TY  - CONF
AU  - Lazić, Anita
AU  - Radovanović, Lidija
AU  - Rogan, Jelena
AU  - Janjić, Goran
AU  - Đorđević, Ivana
AU  - Trišović, Nemanja
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7350
AB  - Proučavano jedinjenje (slika 1) sintetisano je polazeći od cikloheksanona Bučerer- Bergsovom reakcijom i naknadnim acilovanjem dobijenog spirohidantoina. Izgradnja kristalne strukture ovog jedinjenja proučavana je sa aspekta doprinosa jednostavnih dimernih motiva koji se uspostavljaju preko različitih intermolekulskih interakcija.Intermolekulske interakcije dodatno su proučavane pomoću Hiršfeldovih površina i 2D grafičkih prikaza otisaka interakcija. Kristalna struktura, naime, zadržava motiv koji se često sreće kod derivata hidantoina, u kome su dva inverzano orijentisana molekula povezana parom N–H···O vodoničnih veza. Ovaj motiv formira dva tipa dvostrukih lanaca, koji dalje grade sloj (slika 2). Osim toga, slabe C–H⋯O interakcije zajedno sa disperzionim interakcijama (π-π i hidrofobne interakcije) identifikovane su u ovoj kristalnoj strukturi. Kristalografski	podaci:		C19H24N2O3, Mr = 328,4, trikliničan sistem, prostorna grupa P–1, a = 6,2810(2),	b = 12,0586(4),	c = 12,1852(5) Å,α = 77,624(3),	β = 81,039(3),	γ = 79,111(3) °,  V = 878.81(6) Å3, Z = 2, F(000) = 352, ρx = 1,380 g cm–3,µ(MoKα) = 0,084 mm–1. Utačnjavanje sa F2 (220 parametara) dalo je R1 = 0,0520, wR2 = 0,1199, S = 1,033 za sve podatke i R1 = 0,0443 za 3232 uočenih refleksija sa I ≥ 2σ(I).
AB  - The title compound (Figure 1) was prepared from cyclohexanone in the Bucherer-Bergs reaction, followed by acylation of the obtained spirohydantoin. Formation of the crystal structure of this compound was analysed in terms of a number of simple dimeric motifs which are associated with different intermolecular interactions. The crystal structure retains the motif commonly found in hydantoin derivatives, where two molecules related by inversion are linked by a pair of N–H O hydrogen bonds. This motif is involved in two types of double chains, whichfurther form a layer (Figure 2). Intermolecular interactions were also investigated using Hirshfeld surface analysis and 2D fingerprint analysis. Weak C–H⋯O interactions together with thedispersion interactions (π-π and hydrophobic) as the source of attraction are identified in this crystal structure.Crystal data: C19H24N2O3, Mr = 328.4, triclinic system, space group P–1, a = 6.2810(2), b = 12.0586(4), c = 12.1852(5) Å, a = 77.624(3), β = 81.039(3), γ = 79.111(3) °, V = 878.81(6) Å3, Z = 2, F(000) = 352,ρx = 1.380 g cm–3, µ(MoKa) == 0.084 mm–1. The refinement on F2 (220 parameters) yielded R1 = 0.0520, wR2 = 0.1199,S = 1.033 for all data, and R1 = 0.0443 for 3232 observed reflections with I ≥ 2σ(I).
PB  - Beograd : Srpsko kristalografsko društvo
C3  - 28th Conference of the Serbian Crystallographic Society, Abstracts, Čačak, Serbia / XXVIII Konferencija Srpskog kristalografskog društva, Izvodi radova, Čačak, Srbija
T1  - Uloga strukturnih motiva u izgradnji supramolekulske arhitekture 3-(4-terc-butilbenzoil)-1,3-diazaspiro[4.5]Dekan-2,4-diona
T1  - Role of structural motifs in formation of the supramolecular architecture of 3-(4-tert-butylbenzoyl)-1,3-diazaspiro[4.5]Decane-2,4-dione
SP  - 56
EP  - 57
UR  - https://hdl.handle.net/21.15107/rcub_cer_7350
ER  - 

@conference{
author = "Lazić, Anita and Radovanović, Lidija and Rogan, Jelena and Janjić, Goran and Đorđević, Ivana and Trišović, Nemanja",
year = "2023",
abstract = "Proučavano jedinjenje (slika 1) sintetisano je polazeći od cikloheksanona Bučerer- Bergsovom reakcijom i naknadnim acilovanjem dobijenog spirohidantoina. Izgradnja kristalne strukture ovog jedinjenja proučavana je sa aspekta doprinosa jednostavnih dimernih motiva koji se uspostavljaju preko različitih intermolekulskih interakcija.Intermolekulske interakcije dodatno su proučavane pomoću Hiršfeldovih površina i 2D grafičkih prikaza otisaka interakcija. Kristalna struktura, naime, zadržava motiv koji se često sreće kod derivata hidantoina, u kome su dva inverzano orijentisana molekula povezana parom N–H···O vodoničnih veza. Ovaj motiv formira dva tipa dvostrukih lanaca, koji dalje grade sloj (slika 2). Osim toga, slabe C–H⋯O interakcije zajedno sa disperzionim interakcijama (π-π i hidrofobne interakcije) identifikovane su u ovoj kristalnoj strukturi. Kristalografski	podaci:		C19H24N2O3, Mr = 328,4, trikliničan sistem, prostorna grupa P–1, a = 6,2810(2),	b = 12,0586(4),	c = 12,1852(5) Å,α = 77,624(3),	β = 81,039(3),	γ = 79,111(3) °,  V = 878.81(6) Å3, Z = 2, F(000) = 352, ρx = 1,380 g cm–3,µ(MoKα) = 0,084 mm–1. Utačnjavanje sa F2 (220 parametara) dalo je R1 = 0,0520, wR2 = 0,1199, S = 1,033 za sve podatke i R1 = 0,0443 za 3232 uočenih refleksija sa I ≥ 2σ(I)., The title compound (Figure 1) was prepared from cyclohexanone in the Bucherer-Bergs reaction, followed by acylation of the obtained spirohydantoin. Formation of the crystal structure of this compound was analysed in terms of a number of simple dimeric motifs which are associated with different intermolecular interactions. The crystal structure retains the motif commonly found in hydantoin derivatives, where two molecules related by inversion are linked by a pair of N–H O hydrogen bonds. This motif is involved in two types of double chains, whichfurther form a layer (Figure 2). Intermolecular interactions were also investigated using Hirshfeld surface analysis and 2D fingerprint analysis. Weak C–H⋯O interactions together with thedispersion interactions (π-π and hydrophobic) as the source of attraction are identified in this crystal structure.Crystal data: C19H24N2O3, Mr = 328.4, triclinic system, space group P–1, a = 6.2810(2), b = 12.0586(4), c = 12.1852(5) Å, a = 77.624(3), β = 81.039(3), γ = 79.111(3) °, V = 878.81(6) Å3, Z = 2, F(000) = 352,ρx = 1.380 g cm–3, µ(MoKa) == 0.084 mm–1. The refinement on F2 (220 parameters) yielded R1 = 0.0520, wR2 = 0.1199,S = 1.033 for all data, and R1 = 0.0443 for 3232 observed reflections with I ≥ 2σ(I).",
publisher = "Beograd : Srpsko kristalografsko društvo",
journal = "28th Conference of the Serbian Crystallographic Society, Abstracts, Čačak, Serbia / XXVIII Konferencija Srpskog kristalografskog društva, Izvodi radova, Čačak, Srbija",
title = "Uloga strukturnih motiva u izgradnji supramolekulske arhitekture 3-(4-terc-butilbenzoil)-1,3-diazaspiro[4.5]Dekan-2,4-diona, Role of structural motifs in formation of the supramolecular architecture of 3-(4-tert-butylbenzoyl)-1,3-diazaspiro[4.5]Decane-2,4-dione",
pages = "56-57",
url = "https://hdl.handle.net/21.15107/rcub_cer_7350"
}

Lazić, A., Radovanović, L., Rogan, J., Janjić, G., Đorđević, I.,& Trišović, N.. (2023). Uloga strukturnih motiva u izgradnji supramolekulske arhitekture 3-(4-terc-butilbenzoil)-1,3-diazaspiro[4.5]Dekan-2,4-diona. in 28th Conference of the Serbian Crystallographic Society, Abstracts, Čačak, Serbia / XXVIII Konferencija Srpskog kristalografskog društva, Izvodi radova, Čačak, Srbija
Beograd : Srpsko kristalografsko društvo., 56-57.
https://hdl.handle.net/21.15107/rcub_cer_7350

Lazić A, Radovanović L, Rogan J, Janjić G, Đorđević I, Trišović N. Uloga strukturnih motiva u izgradnji supramolekulske arhitekture 3-(4-terc-butilbenzoil)-1,3-diazaspiro[4.5]Dekan-2,4-diona. in 28th Conference of the Serbian Crystallographic Society, Abstracts, Čačak, Serbia / XXVIII Konferencija Srpskog kristalografskog društva, Izvodi radova, Čačak, Srbija. 2023;:56-57.
https://hdl.handle.net/21.15107/rcub_cer_7350 .

Lazić, Anita, Radovanović, Lidija, Rogan, Jelena, Janjić, Goran, Đorđević, Ivana, Trišović, Nemanja, "Uloga strukturnih motiva u izgradnji supramolekulske arhitekture 3-(4-terc-butilbenzoil)-1,3-diazaspiro[4.5]Dekan-2,4-diona" in 28th Conference of the Serbian Crystallographic Society, Abstracts, Čačak, Serbia / XXVIII Konferencija Srpskog kristalografskog društva, Izvodi radova, Čačak, Srbija (2023):56-57,
https://hdl.handle.net/21.15107/rcub_cer_7350 .

TY  - CONF
AU  - Lazić, Anita
AU  - Đorđević, Ivana
AU  - Radovanović, Lidija
AU  - Popović, Dragan
AU  - Rogan, Jelena
AU  - Trišović, Nemanja
AU  - Janjić, Goran
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/6816
AB  - The hierarchical development of the crystal structure of racemic 3-(4-methoxybenzyl)-6,7- benzo-1,3-diazaspiro[4.5]decane-2,4-dione was analyzed through cooperativity of various homo  and heterochiral dimeric motifs associated with the presence of different intermolecular  interactions, namely strong N–H···O and weaker C–H···O, C–H···π and PILOs.1 Although a  bigger number of the contacts in the environment of the tetralin unit results from its larger  contact surface, the 4-methoxybenzyl unit provides a greater contribution to the overall  stabilization. In addition, the investigated compound is identified as a potential inhibitor of  kinase enzymes and AG protein-coupled receptors, with a slightly higher affinity for the later  enzyme. An analysis of the nature of the amino acid residues around the tetralin and 4-methoxy  benzyl units revealed that interactions with nonpolar groups are the most prevalent and even  more numerous than interactions with other amino acid residues (polar, positive and negative).
PB  - COST Action CA21101 "COSY"
C3  - Book of abstracts - COST Training School, COST action CA21101 COSY, "Multiscale modeling of the properties of compounds: From isolated molecules to 3D materials relevant for industrial and astrophysical applications," 19th - 22nd September, 2023, Belgrade
T1  - Self-discriminating assembly and biorecognition of a spirohydantoin derived from α-tetralone
SP  - 47
EP  - 47
UR  - https://hdl.handle.net/21.15107/rcub_cer_6816
ER  - 

@conference{
author = "Lazić, Anita and Đorđević, Ivana and Radovanović, Lidija and Popović, Dragan and Rogan, Jelena and Trišović, Nemanja and Janjić, Goran",
year = "2023",
abstract = "The hierarchical development of the crystal structure of racemic 3-(4-methoxybenzyl)-6,7- benzo-1,3-diazaspiro[4.5]decane-2,4-dione was analyzed through cooperativity of various homo  and heterochiral dimeric motifs associated with the presence of different intermolecular  interactions, namely strong N–H···O and weaker C–H···O, C–H···π and PILOs.1 Although a  bigger number of the contacts in the environment of the tetralin unit results from its larger  contact surface, the 4-methoxybenzyl unit provides a greater contribution to the overall  stabilization. In addition, the investigated compound is identified as a potential inhibitor of  kinase enzymes and AG protein-coupled receptors, with a slightly higher affinity for the later  enzyme. An analysis of the nature of the amino acid residues around the tetralin and 4-methoxy  benzyl units revealed that interactions with nonpolar groups are the most prevalent and even  more numerous than interactions with other amino acid residues (polar, positive and negative).",
publisher = "COST Action CA21101 "COSY"",
journal = "Book of abstracts - COST Training School, COST action CA21101 COSY, "Multiscale modeling of the properties of compounds: From isolated molecules to 3D materials relevant for industrial and astrophysical applications," 19th - 22nd September, 2023, Belgrade",
title = "Self-discriminating assembly and biorecognition of a spirohydantoin derived from α-tetralone",
pages = "47-47",
url = "https://hdl.handle.net/21.15107/rcub_cer_6816"
}

Lazić, A., Đorđević, I., Radovanović, L., Popović, D., Rogan, J., Trišović, N.,& Janjić, G.. (2023). Self-discriminating assembly and biorecognition of a spirohydantoin derived from α-tetralone. in Book of abstracts - COST Training School, COST action CA21101 COSY, "Multiscale modeling of the properties of compounds: From isolated molecules to 3D materials relevant for industrial and astrophysical applications," 19th - 22nd September, 2023, Belgrade
COST Action CA21101 "COSY"., 47-47.
https://hdl.handle.net/21.15107/rcub_cer_6816

Lazić A, Đorđević I, Radovanović L, Popović D, Rogan J, Trišović N, Janjić G. Self-discriminating assembly and biorecognition of a spirohydantoin derived from α-tetralone. in Book of abstracts - COST Training School, COST action CA21101 COSY, "Multiscale modeling of the properties of compounds: From isolated molecules to 3D materials relevant for industrial and astrophysical applications," 19th - 22nd September, 2023, Belgrade. 2023;:47-47.
https://hdl.handle.net/21.15107/rcub_cer_6816 .

Lazić, Anita, Đorđević, Ivana, Radovanović, Lidija, Popović, Dragan, Rogan, Jelena, Trišović, Nemanja, Janjić, Goran, "Self-discriminating assembly and biorecognition of a spirohydantoin derived from α-tetralone" in Book of abstracts - COST Training School, COST action CA21101 COSY, "Multiscale modeling of the properties of compounds: From isolated molecules to 3D materials relevant for industrial and astrophysical applications," 19th - 22nd September, 2023, Belgrade (2023):47-47,
https://hdl.handle.net/21.15107/rcub_cer_6816 .

TY  - JOUR
AU  - Lazić, Anita
AU  - Radovanović, Lidija
AU  - Rogan, Jelena
AU  - Valentić, Nataša
AU  - Janjić, Goran
AU  - Đorđević, Ivana
AU  - Trišović, Nemanja
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7119
AB  - The present study describes representative examples of supramolecular arrangement of 5-phenylhydantoins achieved through various N–H⋯O hydrogen-bonding patterns. Four derivatives, 5-ethyl-5-(4-methylphenyl)hydantoin (1) and three 5-methyl-5-(3- or 4-substituted phenyl)hydantoins (2–4), were synthesized by the Bucherer–Bergs reaction and their crystal structures were determined by the single crystal X-ray diffraction method. A racemate, racemic hydrate and conglomerate as outcomes of crystallization from racemic solutions were found here. The crystal structures were firstly subjected to Hirshfeld surfaces analysis. The development of hydrogen bonding driven two-dimensional assemblies such as tapes, ribbons and sheets was further analysed using DFT calculations in terms of contribution of dimeric motifs as building blocks, which are associated with the presence of intermolecular interactions. To explore qualitative correlations between intermolecular interactions determining the crystal structures of the investigated compounds and those underlying their biological activity, we performed a docking study on the neuronal voltage gated sodium channels, matrix metalloproteinase 12 and aldose reductase. The supramolecular profiles of the investigated compounds are also maintained in biological systems and as such are responsible for differences in their biological activities.
PB  - Royal Society of Chemistry
T2  - CrystEngComm
T1  - Exploring the supramolecular profile of 5-phenylhydantoins
VL  - 25
SP  - 3637
EP  - 3654
DO  - 10.1039/D3CE00213F
ER  - 

@article{
author = "Lazić, Anita and Radovanović, Lidija and Rogan, Jelena and Valentić, Nataša and Janjić, Goran and Đorđević, Ivana and Trišović, Nemanja",
year = "2023",
abstract = "The present study describes representative examples of supramolecular arrangement of 5-phenylhydantoins achieved through various N–H⋯O hydrogen-bonding patterns. Four derivatives, 5-ethyl-5-(4-methylphenyl)hydantoin (1) and three 5-methyl-5-(3- or 4-substituted phenyl)hydantoins (2–4), were synthesized by the Bucherer–Bergs reaction and their crystal structures were determined by the single crystal X-ray diffraction method. A racemate, racemic hydrate and conglomerate as outcomes of crystallization from racemic solutions were found here. The crystal structures were firstly subjected to Hirshfeld surfaces analysis. The development of hydrogen bonding driven two-dimensional assemblies such as tapes, ribbons and sheets was further analysed using DFT calculations in terms of contribution of dimeric motifs as building blocks, which are associated with the presence of intermolecular interactions. To explore qualitative correlations between intermolecular interactions determining the crystal structures of the investigated compounds and those underlying their biological activity, we performed a docking study on the neuronal voltage gated sodium channels, matrix metalloproteinase 12 and aldose reductase. The supramolecular profiles of the investigated compounds are also maintained in biological systems and as such are responsible for differences in their biological activities.",
publisher = "Royal Society of Chemistry",
journal = "CrystEngComm",
title = "Exploring the supramolecular profile of 5-phenylhydantoins",
volume = "25",
pages = "3637-3654",
doi = "10.1039/D3CE00213F"
}

Lazić, A., Radovanović, L., Rogan, J., Valentić, N., Janjić, G., Đorđević, I.,& Trišović, N.. (2023). Exploring the supramolecular profile of 5-phenylhydantoins. in CrystEngComm
Royal Society of Chemistry., 25, 3637-3654.
https://doi.org/10.1039/D3CE00213F

Lazić A, Radovanović L, Rogan J, Valentić N, Janjić G, Đorđević I, Trišović N. Exploring the supramolecular profile of 5-phenylhydantoins. in CrystEngComm. 2023;25:3637-3654.
doi:10.1039/D3CE00213F .

Lazić, Anita, Radovanović, Lidija, Rogan, Jelena, Valentić, Nataša, Janjić, Goran, Đorđević, Ivana, Trišović, Nemanja, "Exploring the supramolecular profile of 5-phenylhydantoins" in CrystEngComm, 25 (2023):3637-3654,
https://doi.org/10.1039/D3CE00213F . .

TY  - CONF
AU  - Lazić, Anita
AU  - Radovanović, Lidija
AU  - Rogan, Jelena
AU  - Janjić, Goran
AU  - Trišović, Nemanja
AU  - Đorđević, Ivana
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7542
AB  - Derivat cikloheksan-5-spirohidantoina (Slika 1) je sintetisan, određena je njegova kristalnastruktura i urađena kvantno-hemijska analiza. Kristalno pakovanje grade mrežesupramolekulskih R64(32) prstenova postavljenih međusobno paralelno, pri čemu seformiraju linearni kanali. Određene su vrednosti energije intermolekulskih interakcija zarazličite dimerne motive dobijene iz kristalne strukture. Uzimajući u razmatranjeprethodno strukturno okarakterisane srodne spirohidantoine [1], dobijena je serijajedinjenja koja je omogućila procenu uticaja supstituenata na njihovu molekulsku ikristalnu strukturu.
AB  - A spirohydantoin derivative (Figure 1) was synthesized and its crystal structure wasdetermined by single crystal X-ray diffraction and analysed by DFT calculations. Thecrystal packing is made of supramolecular nets of R64(32) rings linked together to formstacks that enclose linear channels. The intermolecular interaction energies are quantifiedfor various dimeric motifs. By including the previously reported structurally-relatedspirohydantoins [1], we created a set of compounds that enabled us to evaluate substituenteffects on both molecular and crystal structures.
PB  - Beograd : Srpsko hemijsko društvo
C3  - Kratki izvodi radova ; Knjiga radova / 58. savetovanje Srpskog hemijskog društva, Beograd, 9. i 10. jun 2022. godine
T1  - Proučavanje konformacije i kristalne strukture odabranih derivata cikloheksan-5-spirohidantoina
T1  - Insights into conformational and cristal structure features of selected cyclohexane-5-spirohydantoin derivatives
SP  - 138
EP  - 138
UR  - https://hdl.handle.net/21.15107/rcub_cer_7542
ER  - 

@conference{
author = "Lazić, Anita and Radovanović, Lidija and Rogan, Jelena and Janjić, Goran and Trišović, Nemanja and Đorđević, Ivana",
year = "2022",
abstract = "Derivat cikloheksan-5-spirohidantoina (Slika 1) je sintetisan, određena je njegova kristalnastruktura i urađena kvantno-hemijska analiza. Kristalno pakovanje grade mrežesupramolekulskih R64(32) prstenova postavljenih međusobno paralelno, pri čemu seformiraju linearni kanali. Određene su vrednosti energije intermolekulskih interakcija zarazličite dimerne motive dobijene iz kristalne strukture. Uzimajući u razmatranjeprethodno strukturno okarakterisane srodne spirohidantoine [1], dobijena je serijajedinjenja koja je omogućila procenu uticaja supstituenata na njihovu molekulsku ikristalnu strukturu., A spirohydantoin derivative (Figure 1) was synthesized and its crystal structure wasdetermined by single crystal X-ray diffraction and analysed by DFT calculations. Thecrystal packing is made of supramolecular nets of R64(32) rings linked together to formstacks that enclose linear channels. The intermolecular interaction energies are quantifiedfor various dimeric motifs. By including the previously reported structurally-relatedspirohydantoins [1], we created a set of compounds that enabled us to evaluate substituenteffects on both molecular and crystal structures.",
publisher = "Beograd : Srpsko hemijsko društvo",
journal = "Kratki izvodi radova ; Knjiga radova / 58. savetovanje Srpskog hemijskog društva, Beograd, 9. i 10. jun 2022. godine",
title = "Proučavanje konformacije i kristalne strukture odabranih derivata cikloheksan-5-spirohidantoina, Insights into conformational and cristal structure features of selected cyclohexane-5-spirohydantoin derivatives",
pages = "138-138",
url = "https://hdl.handle.net/21.15107/rcub_cer_7542"
}

Lazić, A., Radovanović, L., Rogan, J., Janjić, G., Trišović, N.,& Đorđević, I.. (2022). Proučavanje konformacije i kristalne strukture odabranih derivata cikloheksan-5-spirohidantoina. in Kratki izvodi radova ; Knjiga radova / 58. savetovanje Srpskog hemijskog društva, Beograd, 9. i 10. jun 2022. godine
Beograd : Srpsko hemijsko društvo., 138-138.
https://hdl.handle.net/21.15107/rcub_cer_7542

Lazić A, Radovanović L, Rogan J, Janjić G, Trišović N, Đorđević I. Proučavanje konformacije i kristalne strukture odabranih derivata cikloheksan-5-spirohidantoina. in Kratki izvodi radova ; Knjiga radova / 58. savetovanje Srpskog hemijskog društva, Beograd, 9. i 10. jun 2022. godine. 2022;:138-138.
https://hdl.handle.net/21.15107/rcub_cer_7542 .

Lazić, Anita, Radovanović, Lidija, Rogan, Jelena, Janjić, Goran, Trišović, Nemanja, Đorđević, Ivana, "Proučavanje konformacije i kristalne strukture odabranih derivata cikloheksan-5-spirohidantoina" in Kratki izvodi radova ; Knjiga radova / 58. savetovanje Srpskog hemijskog društva, Beograd, 9. i 10. jun 2022. godine (2022):138-138,
https://hdl.handle.net/21.15107/rcub_cer_7542 .

TY  - JOUR
AU  - Lazić, Anita
AU  - Radovanović, Lidija
AU  - Gak Simić, Kristina
AU  - Rogan, Jelena
AU  - Janjić, Goran
AU  - Trišović, Nemanja
AU  - Đorđević, Ivana
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5427
AB  - Two spirohydantoin derivatives, 3-(4-chlorobenzoyl)-1,3-diazaspiro[4.5]decane-2,4-dione (1) and 3-(4-bromobenzoyl)-1,3-diazaspiro[4.5]decane-2,4-dione (2), were synthesized and analyzed by single crystal X-ray diffraction, DFT and QTAIM calculations. Simple substitution of the benzoyl unit gave rise to different crystal structures. In 1, a parallel stack along the b-axis with alternating perpendicular separation is formed, while in 2 the R46(32) nets are joined together to form stacks which enclose linear channels. Hierarchical development of these crystal structures was analyzed through dimeric motifs associated with the presence of intermolecular interactions. By including the previously reported structurally-related spirohydantoin derivatives, we created a set of structures which enabled us to evaluate substituent effects on their conformational preferences, i.e., widening of the dihedral angle between the hydantoin and substituted benzoyl unit when going from F to Br. A conformational search revealed that the value of the torsion angle N3-C11-C12-C13 can be regarded as a compromise between the extended conjugation between the carbonyl and phenyl group and intramolecular C-H⋯O interaction between these two groups. This intramolecular effect is more pronounced on the torsion angle C2-N3-C11-C12, which defines the relative orientation between the hydantoin ring and the carbonyl bridge. The present work may provide a basis for design of new cyclohexane-5-spirohydantoins with potential for pharmaceutical applications both at the molecular and supramolecular level.
PB  - USA : Royal Society of Chemistry
T2  - CrystEngComm
T1  - Unravelling conformational and crystal packing preferences of cyclohexane-5-spirohydantoin derivatives incorporating a halogenated benzoyl group
VL  - 24
IS  - 22
SP  - 4106
EP  - 4119
DO  - 10.1039/d2ce00376g
ER  - 

@article{
author = "Lazić, Anita and Radovanović, Lidija and Gak Simić, Kristina and Rogan, Jelena and Janjić, Goran and Trišović, Nemanja and Đorđević, Ivana",
year = "2022",
abstract = "Two spirohydantoin derivatives, 3-(4-chlorobenzoyl)-1,3-diazaspiro[4.5]decane-2,4-dione (1) and 3-(4-bromobenzoyl)-1,3-diazaspiro[4.5]decane-2,4-dione (2), were synthesized and analyzed by single crystal X-ray diffraction, DFT and QTAIM calculations. Simple substitution of the benzoyl unit gave rise to different crystal structures. In 1, a parallel stack along the b-axis with alternating perpendicular separation is formed, while in 2 the R46(32) nets are joined together to form stacks which enclose linear channels. Hierarchical development of these crystal structures was analyzed through dimeric motifs associated with the presence of intermolecular interactions. By including the previously reported structurally-related spirohydantoin derivatives, we created a set of structures which enabled us to evaluate substituent effects on their conformational preferences, i.e., widening of the dihedral angle between the hydantoin and substituted benzoyl unit when going from F to Br. A conformational search revealed that the value of the torsion angle N3-C11-C12-C13 can be regarded as a compromise between the extended conjugation between the carbonyl and phenyl group and intramolecular C-H⋯O interaction between these two groups. This intramolecular effect is more pronounced on the torsion angle C2-N3-C11-C12, which defines the relative orientation between the hydantoin ring and the carbonyl bridge. The present work may provide a basis for design of new cyclohexane-5-spirohydantoins with potential for pharmaceutical applications both at the molecular and supramolecular level.",
publisher = "USA : Royal Society of Chemistry",
journal = "CrystEngComm",
title = "Unravelling conformational and crystal packing preferences of cyclohexane-5-spirohydantoin derivatives incorporating a halogenated benzoyl group",
volume = "24",
number = "22",
pages = "4106-4119",
doi = "10.1039/d2ce00376g"
}

Lazić, A., Radovanović, L., Gak Simić, K., Rogan, J., Janjić, G., Trišović, N.,& Đorđević, I.. (2022). Unravelling conformational and crystal packing preferences of cyclohexane-5-spirohydantoin derivatives incorporating a halogenated benzoyl group. in CrystEngComm
USA : Royal Society of Chemistry., 24(22), 4106-4119.
https://doi.org/10.1039/d2ce00376g

Lazić A, Radovanović L, Gak Simić K, Rogan J, Janjić G, Trišović N, Đorđević I. Unravelling conformational and crystal packing preferences of cyclohexane-5-spirohydantoin derivatives incorporating a halogenated benzoyl group. in CrystEngComm. 2022;24(22):4106-4119.
doi:10.1039/d2ce00376g .

Lazić, Anita, Radovanović, Lidija, Gak Simić, Kristina, Rogan, Jelena, Janjić, Goran, Trišović, Nemanja, Đorđević, Ivana, "Unravelling conformational and crystal packing preferences of cyclohexane-5-spirohydantoin derivatives incorporating a halogenated benzoyl group" in CrystEngComm, 24, no. 22 (2022):4106-4119,
https://doi.org/10.1039/d2ce00376g . .

TY  - CONF
AU  - Lazić, Anita
AU  - Đorđević, Ivana
AU  - Radovanović, Lidija
AU  - Popović, Dragan
AU  - Rogan, Jelena
AU  - Janjić, Goran
AU  - Trišović, Nemanja
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7124
AB  - A racemic spirohydantoin derivative bearing a tetralin and 4-methoxybenzyl group was synthesized
and its crystal structure was determined. The hierarchical development of the crystal packing was
discussed through cooperativity of various homo and heterohiral dimeric motifs associated with the
presence of different intermolecular interactions. A hallmark structural feature of the investigated
compound was alternation of double layers. A larger number of the contact fragments in the
environment of the tetralin unit results from its larger contact surface, while the 4-methoxybenzyl
unit provides a slightly greater contribution to the overall stabilization. Regarding the
pharmacological potential of the investigated compound, we performed a docking study on the
dopamine D3 receptor and IRAK 4 (Interleukin-1 Receptor-Associated Kinase 4) enzyme. The total
number of amino acid, which interact with the 4-methoxybenzyl unit, was slightly larger than the
number of amino acids in the neighborhood of the tetralin unit as a result of its greater flexibility. It
made the 4-methoxybenzyl unit more adaptable for interactions with the biological targets.
PB  - Belgrade : Serbian Chemical Society
C3  - Kratki izvodi radova, Knjiga radova 57. Savetovanje Srpskog hemijskog društva, 18. i 19. juni 2021, Kragujevac / Book of abstracts, Proceedings - 57th Meeting of the Serbian Chemical Society, June 18-19, 2021, Kragujevac, Serbia
T1  - Role of intermolecular interactions in the self-assembly and biorecognition of a spirohydantoin derivative
T1  - Улога интермолекулских интеракција у супрамолекулској организацији и биолошком препознавању деривата спирохидантоина
SP  - 93
EP  - 93
UR  - https://hdl.handle.net/21.15107/rcub_cer_7124
ER  - 

@conference{
author = "Lazić, Anita and Đorđević, Ivana and Radovanović, Lidija and Popović, Dragan and Rogan, Jelena and Janjić, Goran and Trišović, Nemanja",
year = "2021",
abstract = "A racemic spirohydantoin derivative bearing a tetralin and 4-methoxybenzyl group was synthesized
and its crystal structure was determined. The hierarchical development of the crystal packing was
discussed through cooperativity of various homo and heterohiral dimeric motifs associated with the
presence of different intermolecular interactions. A hallmark structural feature of the investigated
compound was alternation of double layers. A larger number of the contact fragments in the
environment of the tetralin unit results from its larger contact surface, while the 4-methoxybenzyl
unit provides a slightly greater contribution to the overall stabilization. Regarding the
pharmacological potential of the investigated compound, we performed a docking study on the
dopamine D3 receptor and IRAK 4 (Interleukin-1 Receptor-Associated Kinase 4) enzyme. The total
number of amino acid, which interact with the 4-methoxybenzyl unit, was slightly larger than the
number of amino acids in the neighborhood of the tetralin unit as a result of its greater flexibility. It
made the 4-methoxybenzyl unit more adaptable for interactions with the biological targets.",
publisher = "Belgrade : Serbian Chemical Society",
journal = "Kratki izvodi radova, Knjiga radova 57. Savetovanje Srpskog hemijskog društva, 18. i 19. juni 2021, Kragujevac / Book of abstracts, Proceedings - 57th Meeting of the Serbian Chemical Society, June 18-19, 2021, Kragujevac, Serbia",
title = "Role of intermolecular interactions in the self-assembly and biorecognition of a spirohydantoin derivative, Улога интермолекулских интеракција у супрамолекулској организацији и биолошком препознавању деривата спирохидантоина",
pages = "93-93",
url = "https://hdl.handle.net/21.15107/rcub_cer_7124"
}

Lazić, A., Đorđević, I., Radovanović, L., Popović, D., Rogan, J., Janjić, G.,& Trišović, N.. (2021). Role of intermolecular interactions in the self-assembly and biorecognition of a spirohydantoin derivative. in Kratki izvodi radova, Knjiga radova 57. Savetovanje Srpskog hemijskog društva, 18. i 19. juni 2021, Kragujevac / Book of abstracts, Proceedings - 57th Meeting of the Serbian Chemical Society, June 18-19, 2021, Kragujevac, Serbia
Belgrade : Serbian Chemical Society., 93-93.
https://hdl.handle.net/21.15107/rcub_cer_7124

Lazić A, Đorđević I, Radovanović L, Popović D, Rogan J, Janjić G, Trišović N. Role of intermolecular interactions in the self-assembly and biorecognition of a spirohydantoin derivative. in Kratki izvodi radova, Knjiga radova 57. Savetovanje Srpskog hemijskog društva, 18. i 19. juni 2021, Kragujevac / Book of abstracts, Proceedings - 57th Meeting of the Serbian Chemical Society, June 18-19, 2021, Kragujevac, Serbia. 2021;:93-93.
https://hdl.handle.net/21.15107/rcub_cer_7124 .

Lazić, Anita, Đorđević, Ivana, Radovanović, Lidija, Popović, Dragan, Rogan, Jelena, Janjić, Goran, Trišović, Nemanja, "Role of intermolecular interactions in the self-assembly and biorecognition of a spirohydantoin derivative" in Kratki izvodi radova, Knjiga radova 57. Savetovanje Srpskog hemijskog društva, 18. i 19. juni 2021, Kragujevac / Book of abstracts, Proceedings - 57th Meeting of the Serbian Chemical Society, June 18-19, 2021, Kragujevac, Serbia (2021):93-93,
https://hdl.handle.net/21.15107/rcub_cer_7124 .

TY  - CONF
AU  - Gak Simić, Kristina
AU  - Lazić, Anita
AU  - Radovanović, Lidija
AU  - Rogan, Jelena
AU  - Janjić, Goran
AU  - Đorđević, Ivana
AU  - Trišović, Nemanja
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7126
AB  - Синтетисан је дериват циклохексан-5-спирохидантоина и одређена је његова кристална
структура. Хијерархијски развој кристалног паковања дискутован је са аспекта кооперативности димерних мотива који настају преко различитих интермолекулских
интеракција, и то: јаких N–H···O водоничних веза и слабих C–H···O, C–H···Cl и C–H···π
интеракција. Кристално паковање задржава мотив, који се обично среће код деривата
хидантоина, у коме су два инверзано оријентисана молекула повезана паром N–H···O
водоничних веза. Специфична структурна карактеристика јесу паралелни слојеви дуж ac-равни. Пошто овај мотив повезује сваки други слој, растојање између слојева се наизменично мења. Накнадна анализа Хиршфелдове површине омогућила је
разраду квалитативних и квантитативних доприноса интермолекулских интеракција
проучаваном кристалном паковању.
AB  - A derivative of cyclohexane-5-spirohydantoin was synthesized and its crystal structure was determined. The hierarchical development of the crystal packing was discussed through cooperativity of various dimeric motifs associated with the presence of different intermolecular interactions, namely strong N–H···O, and weaker C–H···O, C–H···Cl and C–H···π interactions. The crystal packing retained the motif commonly found in hydantoin derivatives where two molecules related by inversion are linked by a pair of N–H∙∙∙O hydrogen bonds. A hallmark structural feature was a parallel layer arrangement to the ac-plane with alternating perpendicular separation, whereby this motif connect every second layer. An analysis of the Hirshfeld surface further elaborated the qualitative and quantitative contributions of intermolecular interactions to the crystal packing.
PB  - Serbian Crystallographic Society
C3  - Изводи радова - XXVII Конференција Српског кристалографског друштва, Крагујевац / Abstracts - 27th Conference of the Serbian crystallographic society , Kragujevac
T1  - Supramolekulska organizacija 3-(4-hlorbenzoil)-1,3- diazaspiro[4.5]dekan-2,4-diona
T1  - Supramolecular association in 3-(4-chlorobenzoyl)-1,3-diazaspiro[4.5]decane-2,4- dione
SP  - 24
EP  - 25
UR  - https://hdl.handle.net/21.15107/rcub_cer_7126
ER  - 

@conference{
author = "Gak Simić, Kristina and Lazić, Anita and Radovanović, Lidija and Rogan, Jelena and Janjić, Goran and Đorđević, Ivana and Trišović, Nemanja",
year = "2021",
abstract = "Синтетисан је дериват циклохексан-5-спирохидантоина и одређена је његова кристална
структура. Хијерархијски развој кристалног паковања дискутован је са аспекта кооперативности димерних мотива који настају преко различитих интермолекулских
интеракција, и то: јаких N–H···O водоничних веза и слабих C–H···O, C–H···Cl и C–H···π
интеракција. Кристално паковање задржава мотив, који се обично среће код деривата
хидантоина, у коме су два инверзано оријентисана молекула повезана паром N–H···O
водоничних веза. Специфична структурна карактеристика јесу паралелни слојеви дуж ac-равни. Пошто овај мотив повезује сваки други слој, растојање између слојева се наизменично мења. Накнадна анализа Хиршфелдове површине омогућила је
разраду квалитативних и квантитативних доприноса интермолекулских интеракција
проучаваном кристалном паковању., A derivative of cyclohexane-5-spirohydantoin was synthesized and its crystal structure was determined. The hierarchical development of the crystal packing was discussed through cooperativity of various dimeric motifs associated with the presence of different intermolecular interactions, namely strong N–H···O, and weaker C–H···O, C–H···Cl and C–H···π interactions. The crystal packing retained the motif commonly found in hydantoin derivatives where two molecules related by inversion are linked by a pair of N–H∙∙∙O hydrogen bonds. A hallmark structural feature was a parallel layer arrangement to the ac-plane with alternating perpendicular separation, whereby this motif connect every second layer. An analysis of the Hirshfeld surface further elaborated the qualitative and quantitative contributions of intermolecular interactions to the crystal packing.",
publisher = "Serbian Crystallographic Society",
journal = "Изводи радова - XXVII Конференција Српског кристалографског друштва, Крагујевац / Abstracts - 27th Conference of the Serbian crystallographic society , Kragujevac",
title = "Supramolekulska organizacija 3-(4-hlorbenzoil)-1,3- diazaspiro[4.5]dekan-2,4-diona, Supramolecular association in 3-(4-chlorobenzoyl)-1,3-diazaspiro[4.5]decane-2,4- dione",
pages = "24-25",
url = "https://hdl.handle.net/21.15107/rcub_cer_7126"
}

Gak Simić, K., Lazić, A., Radovanović, L., Rogan, J., Janjić, G., Đorđević, I.,& Trišović, N.. (2021). Supramolekulska organizacija 3-(4-hlorbenzoil)-1,3- diazaspiro[4.5]dekan-2,4-diona. in Изводи радова - XXVII Конференција Српског кристалографског друштва, Крагујевац / Abstracts - 27th Conference of the Serbian crystallographic society , Kragujevac
Serbian Crystallographic Society., 24-25.
https://hdl.handle.net/21.15107/rcub_cer_7126

Gak Simić K, Lazić A, Radovanović L, Rogan J, Janjić G, Đorđević I, Trišović N. Supramolekulska organizacija 3-(4-hlorbenzoil)-1,3- diazaspiro[4.5]dekan-2,4-diona. in Изводи радова - XXVII Конференција Српског кристалографског друштва, Крагујевац / Abstracts - 27th Conference of the Serbian crystallographic society , Kragujevac. 2021;:24-25.
https://hdl.handle.net/21.15107/rcub_cer_7126 .

Gak Simić, Kristina, Lazić, Anita, Radovanović, Lidija, Rogan, Jelena, Janjić, Goran, Đorđević, Ivana, Trišović, Nemanja, "Supramolekulska organizacija 3-(4-hlorbenzoil)-1,3- diazaspiro[4.5]dekan-2,4-diona" in Изводи радова - XXVII Конференција Српског кристалографског друштва, Крагујевац / Abstracts - 27th Conference of the Serbian crystallographic society , Kragujevac (2021):24-25,
https://hdl.handle.net/21.15107/rcub_cer_7126 .

TY  - CONF
AU  - Janjić, Goran
AU  - Đorđević, Ivana
AU  - Lazić, Anita
AU  - Radovanović, Lidija
AU  - Petković-Benazzouz, Marija
AU  - Rogan, Jelena
AU  - Trišović, Nemanja
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7127
AB  - Kristalografska i kvantnohemijska studija, koja je usmerena na proučavanje efekata fluorovanja benzoil-grupe vezane za cikloheksan-5-spirohidantoin, pokazala je da aromatični prsten ima najveći afinitet prema cikloheksanskom prstenu (nepolarnim grupama), sa kojim gradi C–H∙∙∙π i 
paralelne interakcije sa velikim pomakom. Uvođenje atoma fluora na aromatični prsten dovodi do 
povećanog afiniteta, usled stvaranja dodatnih C–H∙∙∙F interakcija. Dodatno, ova studija je 
proširena na hlorovane i bromovane derivate. Analizom kristalnog pakovanja četiri derivata spirohidantoina (slika) pokazano je da orijentacija aromatičnog prstena, koja je preko rotabilne 
C(aromatični)–C(karbonilni) veze odvojena od rigidnog spirohidantoinskog jezgra, određuje
trodimenzionalnu supramolekulsku arhitekturu. Energijski profil rotabilne veze (slika) jako zavisi 
od vrste halogenog atoma vezanog za aromatični prsten (X). Najvišu barijeru (najmanju rotacionu 
slobodu) ima aromatični prsten sa Br atomom (oko 36 kcal/mol), dok najnižu barijeru imaju 
prstenovi sa vezanim Cl ili F atomom (oko 7 kcal/mol). Izmerene vrednosti torzionog ugla T 
(slika) u kristalnim stukturama, koji definiše rotabilnost ove veze, odgovaraju minimumima energije na energijskim profilima. Kod ovih orijentacija aromatični prstenovi istovremeno grade C–
H...π interakcije sa hidantoinskim prstenom i C–H...O interakciju sa karbonilnom grupom koja 
premošćuje dva prstena. Na osnovu ovih rezultata može se zaključiti da su orijentacije aromatičnog prstena određene unutarmolekulskim interakcijama, a ne međumolekulskim interakcijama, kao i da su konformacione razlike uzrok razlika u kristalnom pakovanju ovih jedinjenja.
AB  - The crystallographic and quantum chemical study, focused on the effects of fluorination of the 
benzoyl group bound to the spirohydantoin moiety, showed that the aromatic ring has the highest 
affinity towards the cyclohexene ring (nonpolar groups), thus forming C–H∙∙∙π and parallel interactions at large offset. Introduction of a fluorine atom into the aromatic ring leads to higher affinity, due to formation of additional C–H∙∙∙F interactions. Subsequently, the present study has been extended to chlorinated and brominated derivatives. An analysis of the crystal packaging of four spirohydantoin derivatives has shown that the orientation of the aromatic ring, bound to the rigid spirohydantoin moiety by the rotatable C(aromatic)–C(carbonyl) bond, determines the three-dimensional supramolecular architecture. The energy profile of the rotatable bond (Figure) strongly depends on the halogen atom bound to the aromatic ring (X). The highest barrier (the lowest rotational freedom) has been found for the aromatic ring with the Br atom (36 kcal/mol), while the rings with the Cl or F atom have the lowest barrier (7 kcal/mol). The measured values of the torsion angle T in the crystal structures which defines the rotability of the mentioned bond, correspond to the energy minima on the energy profiles. In these orientations, the aromatic ring simultaneously forms C–H...π interactions with the hydantoin ring and C–H...O interaction with the carbonyl spacer group. Based on these results, one can conclude that the orientation of the aromatic ring is defined by intramolecular interactions, not by intermolecular interactions, as well as that the conformational differences further cause differences in the crystal packaging of these compounds.
PB  - Serbian Crystallographic Society
C3  - Изводи радова - XXVII Конференција Српског кристалографског друштва, Крагујевац / Abstracts - 27th Conference of the Serbian crystallographic society , Kragujevac
T1  - Uticaj halogenovanja aromatičnog prstena na konformaciju spirohidantoinskih jedinjenja
T1  - Influence of halogenation of aromatic ring on the conformation of spirohydantoin compounds
SP  - 34
EP  - 35
UR  - https://hdl.handle.net/21.15107/rcub_cer_7127
ER  - 

@conference{
author = "Janjić, Goran and Đorđević, Ivana and Lazić, Anita and Radovanović, Lidija and Petković-Benazzouz, Marija and Rogan, Jelena and Trišović, Nemanja",
year = "2021",
abstract = "Kristalografska i kvantnohemijska studija, koja je usmerena na proučavanje efekata fluorovanja benzoil-grupe vezane za cikloheksan-5-spirohidantoin, pokazala je da aromatični prsten ima najveći afinitet prema cikloheksanskom prstenu (nepolarnim grupama), sa kojim gradi C–H∙∙∙π i 
paralelne interakcije sa velikim pomakom. Uvođenje atoma fluora na aromatični prsten dovodi do 
povećanog afiniteta, usled stvaranja dodatnih C–H∙∙∙F interakcija. Dodatno, ova studija je 
proširena na hlorovane i bromovane derivate. Analizom kristalnog pakovanja četiri derivata spirohidantoina (slika) pokazano je da orijentacija aromatičnog prstena, koja je preko rotabilne 
C(aromatični)–C(karbonilni) veze odvojena od rigidnog spirohidantoinskog jezgra, određuje
trodimenzionalnu supramolekulsku arhitekturu. Energijski profil rotabilne veze (slika) jako zavisi 
od vrste halogenog atoma vezanog za aromatični prsten (X). Najvišu barijeru (najmanju rotacionu 
slobodu) ima aromatični prsten sa Br atomom (oko 36 kcal/mol), dok najnižu barijeru imaju 
prstenovi sa vezanim Cl ili F atomom (oko 7 kcal/mol). Izmerene vrednosti torzionog ugla T 
(slika) u kristalnim stukturama, koji definiše rotabilnost ove veze, odgovaraju minimumima energije na energijskim profilima. Kod ovih orijentacija aromatični prstenovi istovremeno grade C–
H...π interakcije sa hidantoinskim prstenom i C–H...O interakciju sa karbonilnom grupom koja 
premošćuje dva prstena. Na osnovu ovih rezultata može se zaključiti da su orijentacije aromatičnog prstena određene unutarmolekulskim interakcijama, a ne međumolekulskim interakcijama, kao i da su konformacione razlike uzrok razlika u kristalnom pakovanju ovih jedinjenja., The crystallographic and quantum chemical study, focused on the effects of fluorination of the 
benzoyl group bound to the spirohydantoin moiety, showed that the aromatic ring has the highest 
affinity towards the cyclohexene ring (nonpolar groups), thus forming C–H∙∙∙π and parallel interactions at large offset. Introduction of a fluorine atom into the aromatic ring leads to higher affinity, due to formation of additional C–H∙∙∙F interactions. Subsequently, the present study has been extended to chlorinated and brominated derivatives. An analysis of the crystal packaging of four spirohydantoin derivatives has shown that the orientation of the aromatic ring, bound to the rigid spirohydantoin moiety by the rotatable C(aromatic)–C(carbonyl) bond, determines the three-dimensional supramolecular architecture. The energy profile of the rotatable bond (Figure) strongly depends on the halogen atom bound to the aromatic ring (X). The highest barrier (the lowest rotational freedom) has been found for the aromatic ring with the Br atom (36 kcal/mol), while the rings with the Cl or F atom have the lowest barrier (7 kcal/mol). The measured values of the torsion angle T in the crystal structures which defines the rotability of the mentioned bond, correspond to the energy minima on the energy profiles. In these orientations, the aromatic ring simultaneously forms C–H...π interactions with the hydantoin ring and C–H...O interaction with the carbonyl spacer group. Based on these results, one can conclude that the orientation of the aromatic ring is defined by intramolecular interactions, not by intermolecular interactions, as well as that the conformational differences further cause differences in the crystal packaging of these compounds.",
publisher = "Serbian Crystallographic Society",
journal = "Изводи радова - XXVII Конференција Српског кристалографског друштва, Крагујевац / Abstracts - 27th Conference of the Serbian crystallographic society , Kragujevac",
title = "Uticaj halogenovanja aromatičnog prstena na konformaciju spirohidantoinskih jedinjenja, Influence of halogenation of aromatic ring on the conformation of spirohydantoin compounds",
pages = "34-35",
url = "https://hdl.handle.net/21.15107/rcub_cer_7127"
}

Janjić, G., Đorđević, I., Lazić, A., Radovanović, L., Petković-Benazzouz, M., Rogan, J.,& Trišović, N.. (2021). Uticaj halogenovanja aromatičnog prstena na konformaciju spirohidantoinskih jedinjenja. in Изводи радова - XXVII Конференција Српског кристалографског друштва, Крагујевац / Abstracts - 27th Conference of the Serbian crystallographic society , Kragujevac
Serbian Crystallographic Society., 34-35.
https://hdl.handle.net/21.15107/rcub_cer_7127

Janjić G, Đorđević I, Lazić A, Radovanović L, Petković-Benazzouz M, Rogan J, Trišović N. Uticaj halogenovanja aromatičnog prstena na konformaciju spirohidantoinskih jedinjenja. in Изводи радова - XXVII Конференција Српског кристалографског друштва, Крагујевац / Abstracts - 27th Conference of the Serbian crystallographic society , Kragujevac. 2021;:34-35.
https://hdl.handle.net/21.15107/rcub_cer_7127 .

Janjić, Goran, Đorđević, Ivana, Lazić, Anita, Radovanović, Lidija, Petković-Benazzouz, Marija, Rogan, Jelena, Trišović, Nemanja, "Uticaj halogenovanja aromatičnog prstena na konformaciju spirohidantoinskih jedinjenja" in Изводи радова - XXVII Конференција Српског кристалографског друштва, Крагујевац / Abstracts - 27th Conference of the Serbian crystallographic society , Kragujevac (2021):34-35,
https://hdl.handle.net/21.15107/rcub_cer_7127 .

TY  - DATA
AU  - Radovanović, Lidija D.
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4510
AB  - UREZID : 3-(3,5-dimethylpyridin-1-ium-1-yl)-4-methyl-6-oxo-1,6-dihydropyridin-2-olate tetrahydrate Space Group: P 1 (2), Cell: a 7.4411(15)Å b 10.581(2)Å c 11.235(2)Å, α 108.96(3)° β 96.14(3)° γ 107.41(3)°
PB  - The Cambridge Crystallographic Data Centre (CCDC)
T1  - CCDC 2057270: Experimental Crystal Structure Determination. Crystallographic data for "Charge assisted assembly of zwitterionic pyridone hydrates"
DO  - 10.5517/ccdc.csd.cc271rkm
ER  - 

@misc{
author = "Radovanović, Lidija D.",
year = "2021",
abstract = "UREZID : 3-(3,5-dimethylpyridin-1-ium-1-yl)-4-methyl-6-oxo-1,6-dihydropyridin-2-olate tetrahydrate Space Group: P 1 (2), Cell: a 7.4411(15)Å b 10.581(2)Å c 11.235(2)Å, α 108.96(3)° β 96.14(3)° γ 107.41(3)°",
publisher = "The Cambridge Crystallographic Data Centre (CCDC)",
title = "CCDC 2057270: Experimental Crystal Structure Determination. Crystallographic data for "Charge assisted assembly of zwitterionic pyridone hydrates"",
doi = "10.5517/ccdc.csd.cc271rkm"
}

Radovanović, L. D.. (2021). CCDC 2057270: Experimental Crystal Structure Determination. Crystallographic data for "Charge assisted assembly of zwitterionic pyridone hydrates". 
The Cambridge Crystallographic Data Centre (CCDC)..
https://doi.org/10.5517/ccdc.csd.cc271rkm

Radovanović LD. CCDC 2057270: Experimental Crystal Structure Determination. Crystallographic data for "Charge assisted assembly of zwitterionic pyridone hydrates". 2021;.
doi:10.5517/ccdc.csd.cc271rkm .

Radovanović, Lidija D., "CCDC 2057270: Experimental Crystal Structure Determination. Crystallographic data for "Charge assisted assembly of zwitterionic pyridone hydrates"" (2021),
https://doi.org/10.5517/ccdc.csd.cc271rkm . .

TY  - DATA
AU  - Radovanović, Lidija D.
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4509
AB  - UREZEZ : 4-methyl-6-oxo-5-(pyridin-1-ium-1-yl)-1,6-dihydropyridin-2-olate dihydrate Space Group: P 1 (2), Cell: a 7.2258(14)Å b 8.0470(16)Å c 11.287(2)Å, α 70.71(3)° β 74.88(3)° γ 79.85(3)°
PB  - The Cambridge Crystallographic Data Centre (CCDC)
T1  - CCDC 2057269: Experimental Crystal Structure Determination. Crystallographic data for "Charge assisted assembly of zwitterionic pyridone hydrates"
DO  - 10.5517/ccdc.csd.cc271rjl
ER  - 

@misc{
author = "Radovanović, Lidija D.",
year = "2021",
abstract = "UREZEZ : 4-methyl-6-oxo-5-(pyridin-1-ium-1-yl)-1,6-dihydropyridin-2-olate dihydrate Space Group: P 1 (2), Cell: a 7.2258(14)Å b 8.0470(16)Å c 11.287(2)Å, α 70.71(3)° β 74.88(3)° γ 79.85(3)°",
publisher = "The Cambridge Crystallographic Data Centre (CCDC)",
title = "CCDC 2057269: Experimental Crystal Structure Determination. Crystallographic data for "Charge assisted assembly of zwitterionic pyridone hydrates"",
doi = "10.5517/ccdc.csd.cc271rjl"
}

Radovanović, L. D.. (2021). CCDC 2057269: Experimental Crystal Structure Determination. Crystallographic data for "Charge assisted assembly of zwitterionic pyridone hydrates". 
The Cambridge Crystallographic Data Centre (CCDC)..
https://doi.org/10.5517/ccdc.csd.cc271rjl

Radovanović LD. CCDC 2057269: Experimental Crystal Structure Determination. Crystallographic data for "Charge assisted assembly of zwitterionic pyridone hydrates". 2021;.
doi:10.5517/ccdc.csd.cc271rjl .

Radovanović, Lidija D., "CCDC 2057269: Experimental Crystal Structure Determination. Crystallographic data for "Charge assisted assembly of zwitterionic pyridone hydrates"" (2021),
https://doi.org/10.5517/ccdc.csd.cc271rjl . .

TY  - DATA
AU  - Mašulović, Aleksandra D.
AU  - Lađarević, Jelena M.
AU  - Radovanović, Lidija D.
AU  - Vitnik, Željko
AU  - Vitnik, Vesna
AU  - Rogan, Jelena R.
AU  - Mijin, Dušan
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4508
AB  - Fig. S1 Optimized geometry forms of compound 1 without (1a, 1b, 1c) and with water molecules (1d ,1e, 1f). Table S1 Optimized geometry forms of compound 1·2H2O in comparison with experimental data. Fig. S2 Optimized geometry forms of compound 2 without (2a, 2b, 2c) and with water molecules (2d, 2e, 2f). Table S2 Optimized geometry forms of compound 2·4H2O in comparison with experimental data. Fig. S3 NBO charges of 1a and 1b forms of the compound 1. Table S3 NBO charge of 1a and 1b forms of the compound 1. Fig. S4 The structural segment of 1·2H2O containing water molecule W2. Fig. S5 The structural segment of 2·4H2O containing interlayer water molecule W4. Fig. S6 Hirshfeld surface analysis of 1 without (a) and with (b) zwitterion-water interactions included. Fig. S7 Hirshfeld surface analysis of 2 without (a) and with (b) zwitterion-water interactions included. Fig. S8 Comparable PES study of 1 and 2 with biphenyl. Fig S9. Optimized geometry forms affected by crystal network of compounds 1·2H2O and 2·4H2O. Table S4 Optimized geometry forms of compound 1·2H2O in comparison with experimental data. Table S5 Optimized geometry forms of compound 2·4H2O in comparison with experimental data.
PB  - Elsevier
T2  - Journal of Molecular Structure
T1  - Supporting material for: "Charge assisted assembly of zwitterionic pyridone hydrates"
UR  - https://hdl.handle.net/21.15107/rcub_cer_4508
ER  - 

@misc{
author = "Mašulović, Aleksandra D. and Lađarević, Jelena M. and Radovanović, Lidija D. and Vitnik, Željko and Vitnik, Vesna and Rogan, Jelena R. and Mijin, Dušan",
year = "2021",
abstract = "Fig. S1 Optimized geometry forms of compound 1 without (1a, 1b, 1c) and with water molecules (1d ,1e, 1f). Table S1 Optimized geometry forms of compound 1·2H2O in comparison with experimental data. Fig. S2 Optimized geometry forms of compound 2 without (2a, 2b, 2c) and with water molecules (2d, 2e, 2f). Table S2 Optimized geometry forms of compound 2·4H2O in comparison with experimental data. Fig. S3 NBO charges of 1a and 1b forms of the compound 1. Table S3 NBO charge of 1a and 1b forms of the compound 1. Fig. S4 The structural segment of 1·2H2O containing water molecule W2. Fig. S5 The structural segment of 2·4H2O containing interlayer water molecule W4. Fig. S6 Hirshfeld surface analysis of 1 without (a) and with (b) zwitterion-water interactions included. Fig. S7 Hirshfeld surface analysis of 2 without (a) and with (b) zwitterion-water interactions included. Fig. S8 Comparable PES study of 1 and 2 with biphenyl. Fig S9. Optimized geometry forms affected by crystal network of compounds 1·2H2O and 2·4H2O. Table S4 Optimized geometry forms of compound 1·2H2O in comparison with experimental data. Table S5 Optimized geometry forms of compound 2·4H2O in comparison with experimental data.",
publisher = "Elsevier",
journal = "Journal of Molecular Structure",
title = "Supporting material for: "Charge assisted assembly of zwitterionic pyridone hydrates"",
url = "https://hdl.handle.net/21.15107/rcub_cer_4508"
}

Mašulović, A. D., Lađarević, J. M., Radovanović, L. D., Vitnik, Ž., Vitnik, V., Rogan, J. R.,& Mijin, D.. (2021). Supporting material for: "Charge assisted assembly of zwitterionic pyridone hydrates". in Journal of Molecular Structure
Elsevier..
https://hdl.handle.net/21.15107/rcub_cer_4508

Mašulović AD, Lađarević JM, Radovanović LD, Vitnik Ž, Vitnik V, Rogan JR, Mijin D. Supporting material for: "Charge assisted assembly of zwitterionic pyridone hydrates". in Journal of Molecular Structure. 2021;.
https://hdl.handle.net/21.15107/rcub_cer_4508 .

Mašulović, Aleksandra D., Lađarević, Jelena M., Radovanović, Lidija D., Vitnik, Željko, Vitnik, Vesna, Rogan, Jelena R., Mijin, Dušan, "Supporting material for: "Charge assisted assembly of zwitterionic pyridone hydrates"" in Journal of Molecular Structure (2021),
https://hdl.handle.net/21.15107/rcub_cer_4508 .

TY  - JOUR
AU  - Mašulović, Aleksandra D.
AU  - Lađarević, Jelena M.
AU  - Radovanović, Lidija D.
AU  - Vitnik, Željko
AU  - Vitnik, Vesna
AU  - Rogan, Jelena R.
AU  - Mijin, Dušan
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4507
AB  - Two pyridone derivatives, bearing the pyridinium moiety (1), or dimethylpyridinium moiety (2), have been synthesized and their crystal structures have been determined. The compounds crystalize in hydrated zwitterionic forms with either two (1•2H2O) or four (2•4H2O) water molecules. The zwitterionic networks contain different types of water clusters, generated into channels, incorporating them into the network by sandwiching. The type of channel depends on the crystal lattice and the nature of non-covalent interactions established between zwitterions as well as the number of water molecules incorporated into the architecture. 1 affords tubes filled in with water channels formed by water tetramers, contrary to 2, which affords a layered network altering the zwitterionic layer and the layer formed by water tetramers and hexamers. A detailed study of intermolecular interactions of both crystal structures and a quantification of interaction energies has been performed using PIXEL lattice energy calculations, giving an insight to a quantitative evaluation of interactions through Coulombic, disperse, repulsion and polarization energies. The strongest pairwise, in both structures, is found to be a dipole–dipole interaction between oppositely charged heterocyclic rings. The differences in the crystal packings of these hydrates have been elucidated by the fingerplot analysis. The comparative studies between experimental and calculated (DFT) data of molecules 1•H2O and 2•4H2O for systems of different complexity are performed. Furthermore, correlations of experimental and calculated bond lengths and the simulation of compound solvation with the CPCM model are done.
PB  - Elsevier
T2  - Journal of Molecular Structure
T1  - Charge assisted assembly of zwitterionic pyridone hydrates
VL  - 1237
SP  - 130419
DO  - 10.1016/j.molstruc.2021.130419
ER  - 

@article{
author = "Mašulović, Aleksandra D. and Lađarević, Jelena M. and Radovanović, Lidija D. and Vitnik, Željko and Vitnik, Vesna and Rogan, Jelena R. and Mijin, Dušan",
year = "2021",
abstract = "Two pyridone derivatives, bearing the pyridinium moiety (1), or dimethylpyridinium moiety (2), have been synthesized and their crystal structures have been determined. The compounds crystalize in hydrated zwitterionic forms with either two (1•2H2O) or four (2•4H2O) water molecules. The zwitterionic networks contain different types of water clusters, generated into channels, incorporating them into the network by sandwiching. The type of channel depends on the crystal lattice and the nature of non-covalent interactions established between zwitterions as well as the number of water molecules incorporated into the architecture. 1 affords tubes filled in with water channels formed by water tetramers, contrary to 2, which affords a layered network altering the zwitterionic layer and the layer formed by water tetramers and hexamers. A detailed study of intermolecular interactions of both crystal structures and a quantification of interaction energies has been performed using PIXEL lattice energy calculations, giving an insight to a quantitative evaluation of interactions through Coulombic, disperse, repulsion and polarization energies. The strongest pairwise, in both structures, is found to be a dipole–dipole interaction between oppositely charged heterocyclic rings. The differences in the crystal packings of these hydrates have been elucidated by the fingerplot analysis. The comparative studies between experimental and calculated (DFT) data of molecules 1•H2O and 2•4H2O for systems of different complexity are performed. Furthermore, correlations of experimental and calculated bond lengths and the simulation of compound solvation with the CPCM model are done.",
publisher = "Elsevier",
journal = "Journal of Molecular Structure",
title = "Charge assisted assembly of zwitterionic pyridone hydrates",
volume = "1237",
pages = "130419",
doi = "10.1016/j.molstruc.2021.130419"
}

Mašulović, A. D., Lađarević, J. M., Radovanović, L. D., Vitnik, Ž., Vitnik, V., Rogan, J. R.,& Mijin, D.. (2021). Charge assisted assembly of zwitterionic pyridone hydrates. in Journal of Molecular Structure
Elsevier., 1237, 130419.
https://doi.org/10.1016/j.molstruc.2021.130419

Mašulović AD, Lađarević JM, Radovanović LD, Vitnik Ž, Vitnik V, Rogan JR, Mijin D. Charge assisted assembly of zwitterionic pyridone hydrates. in Journal of Molecular Structure. 2021;1237:130419.
doi:10.1016/j.molstruc.2021.130419 .

Mašulović, Aleksandra D., Lađarević, Jelena M., Radovanović, Lidija D., Vitnik, Željko, Vitnik, Vesna, Rogan, Jelena R., Mijin, Dušan, "Charge assisted assembly of zwitterionic pyridone hydrates" in Journal of Molecular Structure, 1237 (2021):130419,
https://doi.org/10.1016/j.molstruc.2021.130419 . .

TY  - JOUR
AU  - Mašulović, Aleksandra D.
AU  - Lađarević, Jelena M.
AU  - Radovanović, Lidija D.
AU  - Vitnik, Željko
AU  - Vitnik, Vesna
AU  - Rogan, Jelena R.
AU  - Mijin, Dušan
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4506
AB  - Two pyridone derivatives, bearing the pyridinium moiety (1), or dimethylpyridinium moiety (2), have been synthesized and their crystal structures have been determined. The compounds crystalize in hydrated zwitterionic forms with either two (1•2H2O) or four (2•4H2O) water molecules. The zwitterionic networks contain different types of water clusters, generated into channels, incorporating them into the network by sandwiching. The type of channel depends on the crystal lattice and the nature of non-covalent interactions established between zwitterions as well as the number of water molecules incorporated into the architecture. 1 affords tubes filled in with water channels formed by water tetramers, contrary to 2, which affords a layered network altering the zwitterionic layer and the layer formed by water tetramers and hexamers. A detailed study of intermolecular interactions of both crystal structures and a quantification of interaction energies has been performed using PIXEL lattice energy calculations, giving an insight to a quantitative evaluation of interactions through Coulombic, disperse, repulsion and polarization energies. The strongest pairwise, in both structures, is found to be a dipole–dipole interaction between oppositely charged heterocyclic rings. The differences in the crystal packings of these hydrates have been elucidated by the fingerplot analysis. The comparative studies between experimental and calculated (DFT) data of molecules 1•H2O and 2•4H2O for systems of different complexity are performed. Furthermore, correlations of experimental and calculated bond lengths and the simulation of compound solvation with the CPCM model are done.
PB  - Elsevier
T2  - Journal of Molecular Structure
T1  - Charge assisted assembly of zwitterionic pyridone hydrates
VL  - 1237
SP  - 130419
DO  - 10.1016/j.molstruc.2021.130419
ER  - 

@article{
author = "Mašulović, Aleksandra D. and Lađarević, Jelena M. and Radovanović, Lidija D. and Vitnik, Željko and Vitnik, Vesna and Rogan, Jelena R. and Mijin, Dušan",
year = "2021",
abstract = "Two pyridone derivatives, bearing the pyridinium moiety (1), or dimethylpyridinium moiety (2), have been synthesized and their crystal structures have been determined. The compounds crystalize in hydrated zwitterionic forms with either two (1•2H2O) or four (2•4H2O) water molecules. The zwitterionic networks contain different types of water clusters, generated into channels, incorporating them into the network by sandwiching. The type of channel depends on the crystal lattice and the nature of non-covalent interactions established between zwitterions as well as the number of water molecules incorporated into the architecture. 1 affords tubes filled in with water channels formed by water tetramers, contrary to 2, which affords a layered network altering the zwitterionic layer and the layer formed by water tetramers and hexamers. A detailed study of intermolecular interactions of both crystal structures and a quantification of interaction energies has been performed using PIXEL lattice energy calculations, giving an insight to a quantitative evaluation of interactions through Coulombic, disperse, repulsion and polarization energies. The strongest pairwise, in both structures, is found to be a dipole–dipole interaction between oppositely charged heterocyclic rings. The differences in the crystal packings of these hydrates have been elucidated by the fingerplot analysis. The comparative studies between experimental and calculated (DFT) data of molecules 1•H2O and 2•4H2O for systems of different complexity are performed. Furthermore, correlations of experimental and calculated bond lengths and the simulation of compound solvation with the CPCM model are done.",
publisher = "Elsevier",
journal = "Journal of Molecular Structure",
title = "Charge assisted assembly of zwitterionic pyridone hydrates",
volume = "1237",
pages = "130419",
doi = "10.1016/j.molstruc.2021.130419"
}

Mašulović, A. D., Lađarević, J. M., Radovanović, L. D., Vitnik, Ž., Vitnik, V., Rogan, J. R.,& Mijin, D.. (2021). Charge assisted assembly of zwitterionic pyridone hydrates. in Journal of Molecular Structure
Elsevier., 1237, 130419.
https://doi.org/10.1016/j.molstruc.2021.130419

Mašulović AD, Lađarević JM, Radovanović LD, Vitnik Ž, Vitnik V, Rogan JR, Mijin D. Charge assisted assembly of zwitterionic pyridone hydrates. in Journal of Molecular Structure. 2021;1237:130419.
doi:10.1016/j.molstruc.2021.130419 .

Mašulović, Aleksandra D., Lađarević, Jelena M., Radovanović, Lidija D., Vitnik, Željko, Vitnik, Vesna, Rogan, Jelena R., Mijin, Dušan, "Charge assisted assembly of zwitterionic pyridone hydrates" in Journal of Molecular Structure, 1237 (2021):130419,
https://doi.org/10.1016/j.molstruc.2021.130419 . .

TY  - JOUR
AU  - Gak Simić, Kristina
AU  - Đorđević, Ivana S.
AU  - Lazić, Anita M.
AU  - Radovanović, Lidija D.
AU  - Petković-Benazzouz, Marija
AU  - Rogan, Jelena R.
AU  - Trišović, Nemanja
AU  - Janjić, Goran
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4678
AB  - The quantitative assessment of intermolecular interactions and their cooperative effects has been performed in spirohydantoin-based model compounds, 3-benzoyl-1,3-diazaspiro[4.5]decane-2,4-dione (1) and 3-(4-fluorobenzoyl)-1,3-diazaspiro[4.5]decane-2,4-dione (2), through single crystal X-ray crystallography and quantum chemical studies. In both crystal structures, molecules generate the same hydrogen-bonded centrosymmetric R22(8) synthon. The extended supramolecular architectures depend on the C-HO, C-Hπ, stacking interactions and parallel interactions at large offsets, which lead to molecular sheets and further, with the assistance of the C-HF interaction in the case of2, to three-dimensional networks. Electrostatic potential maps have indicated that formation of the intermolecular FF interaction in the crystal structure of2results in a new region with a larger surface area and a higher negative potential in comparison to the individual fluorine atoms. Establishment of this interaction leads to strengthening of the interaction of one of the fluorine atoms with a third molecule from the environment which does not interact with both of them. When this third molecule interacts with both fluorine atoms simultaneously, the calculations have shown that the effect of strengthening of the individual interactions due to formation of the FF interaction is absent.
PB  - Royal Society of Chemistry
T2  - CrystEngComm
T1  - On the supramolecular outcomes of fluorination of cyclohexane-5-spirohydantoin derivatives
VL  - 23
IS  - 13
SP  - 2606
EP  - 2622
DO  - 10.1039/d0ce01841d
ER  - 

@article{
author = "Gak Simić, Kristina and Đorđević, Ivana S. and Lazić, Anita M. and Radovanović, Lidija D. and Petković-Benazzouz, Marija and Rogan, Jelena R. and Trišović, Nemanja and Janjić, Goran",
year = "2021",
abstract = "The quantitative assessment of intermolecular interactions and their cooperative effects has been performed in spirohydantoin-based model compounds, 3-benzoyl-1,3-diazaspiro[4.5]decane-2,4-dione (1) and 3-(4-fluorobenzoyl)-1,3-diazaspiro[4.5]decane-2,4-dione (2), through single crystal X-ray crystallography and quantum chemical studies. In both crystal structures, molecules generate the same hydrogen-bonded centrosymmetric R22(8) synthon. The extended supramolecular architectures depend on the C-HO, C-Hπ, stacking interactions and parallel interactions at large offsets, which lead to molecular sheets and further, with the assistance of the C-HF interaction in the case of2, to three-dimensional networks. Electrostatic potential maps have indicated that formation of the intermolecular FF interaction in the crystal structure of2results in a new region with a larger surface area and a higher negative potential in comparison to the individual fluorine atoms. Establishment of this interaction leads to strengthening of the interaction of one of the fluorine atoms with a third molecule from the environment which does not interact with both of them. When this third molecule interacts with both fluorine atoms simultaneously, the calculations have shown that the effect of strengthening of the individual interactions due to formation of the FF interaction is absent.",
publisher = "Royal Society of Chemistry",
journal = "CrystEngComm",
title = "On the supramolecular outcomes of fluorination of cyclohexane-5-spirohydantoin derivatives",
volume = "23",
number = "13",
pages = "2606-2622",
doi = "10.1039/d0ce01841d"
}

Gak Simić, K., Đorđević, I. S., Lazić, A. M., Radovanović, L. D., Petković-Benazzouz, M., Rogan, J. R., Trišović, N.,& Janjić, G.. (2021). On the supramolecular outcomes of fluorination of cyclohexane-5-spirohydantoin derivatives. in CrystEngComm
Royal Society of Chemistry., 23(13), 2606-2622.
https://doi.org/10.1039/d0ce01841d

Gak Simić K, Đorđević IS, Lazić AM, Radovanović LD, Petković-Benazzouz M, Rogan JR, Trišović N, Janjić G. On the supramolecular outcomes of fluorination of cyclohexane-5-spirohydantoin derivatives. in CrystEngComm. 2021;23(13):2606-2622.
doi:10.1039/d0ce01841d .

Gak Simić, Kristina, Đorđević, Ivana S., Lazić, Anita M., Radovanović, Lidija D., Petković-Benazzouz, Marija, Rogan, Jelena R., Trišović, Nemanja, Janjić, Goran, "On the supramolecular outcomes of fluorination of cyclohexane-5-spirohydantoin derivatives" in CrystEngComm, 23, no. 13 (2021):2606-2622,
https://doi.org/10.1039/d0ce01841d . .

TY  - JOUR
AU  - Lazić, Anita M.
AU  - Đorđević, Ivana
AU  - Radovanović, Lidija
AU  - Popović, Dragan
AU  - Rogan, Jelena R.
AU  - Janjić, Goran
AU  - Trišović, Nemanja
PY  - 2020
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3638
AB  - A racemic spirohydantoin derivative with two aromatic substituents, a tetralin and a 4-methoxybenzyl unit, was synthesized and its crystal structure was determined. To define the relationship between molecular stereochemistry and spatial association modes, development of the crystal packing was analyzed through cooperativity of intermolecular interactions. Homo and heterochiral dimeric motifs were stabilized by intermolecular N−H⋅⋅⋅O, C−H⋅⋅⋅O, C−H⋅⋅⋅π interactions and parallel interactions at large offsets (PILO), thus forming alternating double layers. The greatest contribution to the total stabilization came from a motif of opposite enantiomers linked by N−H⋅⋅⋅O bonds (interaction energy=−13.72 kcal/mol), followed by a homochiral motif where the 4-methoxybenzyl units allowed C−H⋅⋅⋅π, C−H⋅⋅⋅O interactions and PILO (interaction energy=−11.56 kcal/mol). The number of the contact fragments in the environment of the tetralin unit was larger, but the 4-methoxybenzyl unit had greater contribution to the total stabilization. The statistical analysis of the data from the Cambridge Structural Database (CSD) showed that this is a general trend. The compound is a potential inhibitor of kinase enzymes and antigen protein-coupled receptors. A correlation between the docking study and the results of the CSD analysis can be drawn. Due to a greater flexibility, the 4-methoxybenzyl unit is more adaptable for interactions with the biological targets than the tetralin unit.
PB  - John Wiley and Sons Inc
T2  - ChemPlusChem
T1  - Self-Assembly and Biorecognition of a Spirohydantoin Derived from α-Tetralone: Interplay between Chirality and Intermolecular Interactions
VL  - 85
IS  - 6
SP  - 1220
EP  - 1232
DO  - 10.1002/cplu.202000273
ER  - 

@article{
author = "Lazić, Anita M. and Đorđević, Ivana and Radovanović, Lidija and Popović, Dragan and Rogan, Jelena R. and Janjić, Goran and Trišović, Nemanja",
year = "2020",
abstract = "A racemic spirohydantoin derivative with two aromatic substituents, a tetralin and a 4-methoxybenzyl unit, was synthesized and its crystal structure was determined. To define the relationship between molecular stereochemistry and spatial association modes, development of the crystal packing was analyzed through cooperativity of intermolecular interactions. Homo and heterochiral dimeric motifs were stabilized by intermolecular N−H⋅⋅⋅O, C−H⋅⋅⋅O, C−H⋅⋅⋅π interactions and parallel interactions at large offsets (PILO), thus forming alternating double layers. The greatest contribution to the total stabilization came from a motif of opposite enantiomers linked by N−H⋅⋅⋅O bonds (interaction energy=−13.72 kcal/mol), followed by a homochiral motif where the 4-methoxybenzyl units allowed C−H⋅⋅⋅π, C−H⋅⋅⋅O interactions and PILO (interaction energy=−11.56 kcal/mol). The number of the contact fragments in the environment of the tetralin unit was larger, but the 4-methoxybenzyl unit had greater contribution to the total stabilization. The statistical analysis of the data from the Cambridge Structural Database (CSD) showed that this is a general trend. The compound is a potential inhibitor of kinase enzymes and antigen protein-coupled receptors. A correlation between the docking study and the results of the CSD analysis can be drawn. Due to a greater flexibility, the 4-methoxybenzyl unit is more adaptable for interactions with the biological targets than the tetralin unit.",
publisher = "John Wiley and Sons Inc",
journal = "ChemPlusChem",
title = "Self-Assembly and Biorecognition of a Spirohydantoin Derived from α-Tetralone: Interplay between Chirality and Intermolecular Interactions",
volume = "85",
number = "6",
pages = "1220-1232",
doi = "10.1002/cplu.202000273"
}

Lazić, A. M., Đorđević, I., Radovanović, L., Popović, D., Rogan, J. R., Janjić, G.,& Trišović, N.. (2020). Self-Assembly and Biorecognition of a Spirohydantoin Derived from α-Tetralone: Interplay between Chirality and Intermolecular Interactions. in ChemPlusChem
John Wiley and Sons Inc., 85(6), 1220-1232.
https://doi.org/10.1002/cplu.202000273

Lazić AM, Đorđević I, Radovanović L, Popović D, Rogan JR, Janjić G, Trišović N. Self-Assembly and Biorecognition of a Spirohydantoin Derived from α-Tetralone: Interplay between Chirality and Intermolecular Interactions. in ChemPlusChem. 2020;85(6):1220-1232.
doi:10.1002/cplu.202000273 .

Lazić, Anita M., Đorđević, Ivana, Radovanović, Lidija, Popović, Dragan, Rogan, Jelena R., Janjić, Goran, Trišović, Nemanja, "Self-Assembly and Biorecognition of a Spirohydantoin Derived from α-Tetralone: Interplay between Chirality and Intermolecular Interactions" in ChemPlusChem, 85, no. 6 (2020):1220-1232,
https://doi.org/10.1002/cplu.202000273 . .

TY  - JOUR
AU  - Lazić, Anita M.
AU  - Đorđević, Ivana
AU  - Radovanović, Lidija
AU  - Popović, Dragan
AU  - Rogan, Jelena R.
AU  - Janjić, Goran
AU  - Trišović, Nemanja
PY  - 2020
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3716
AB  - A racemic spirohydantoin derivative with two aromatic substituents, a tetralin and a 4-methoxybenzyl unit, was synthesized and its crystal structure was determined. To define the relationship between molecular stereochemistry and spatial association modes, development of the crystal packing was analyzed through cooperativity of intermolecular interactions. Homo and heterochiral dimeric motifs were stabilized by intermolecular N−H⋅⋅⋅O, C−H⋅⋅⋅O, C−H⋅⋅⋅π interactions and parallel interactions at large offsets (PILO), thus forming alternating double layers. The greatest contribution to the total stabilization came from a motif of opposite enantiomers linked by N−H⋅⋅⋅O bonds (interaction energy=−13.72 kcal/mol), followed by a homochiral motif where the 4-methoxybenzyl units allowed C−H⋅⋅⋅π, C−H⋅⋅⋅O interactions and PILO (interaction energy=−11.56 kcal/mol). The number of the contact fragments in the environment of the tetralin unit was larger, but the 4-methoxybenzyl unit had greater contribution to the total stabilization. The statistical analysis of the data from the Cambridge Structural Database (CSD) showed that this is a general trend. The compound is a potential inhibitor of kinase enzymes and antigen protein-coupled receptors. A correlation between the docking study and the results of the CSD analysis can be drawn. Due to a greater flexibility, the 4-methoxybenzyl unit is more adaptable for interactions with the biological targets than the tetralin unit.
PB  - John Wiley and Sons Inc.
T2  - ChemPlusChem
T1  - Self-Assembly and Biorecognition of a Spirohydantoin Derived from α-Tetralone: Interplay between Chirality and Intermolecular Interactions
VL  - 85
IS  - 6
SP  - 1220
EP  - 1232
DO  - 10.1002/cplu.202000273
ER  - 

@article{
author = "Lazić, Anita M. and Đorđević, Ivana and Radovanović, Lidija and Popović, Dragan and Rogan, Jelena R. and Janjić, Goran and Trišović, Nemanja",
year = "2020",
abstract = "A racemic spirohydantoin derivative with two aromatic substituents, a tetralin and a 4-methoxybenzyl unit, was synthesized and its crystal structure was determined. To define the relationship between molecular stereochemistry and spatial association modes, development of the crystal packing was analyzed through cooperativity of intermolecular interactions. Homo and heterochiral dimeric motifs were stabilized by intermolecular N−H⋅⋅⋅O, C−H⋅⋅⋅O, C−H⋅⋅⋅π interactions and parallel interactions at large offsets (PILO), thus forming alternating double layers. The greatest contribution to the total stabilization came from a motif of opposite enantiomers linked by N−H⋅⋅⋅O bonds (interaction energy=−13.72 kcal/mol), followed by a homochiral motif where the 4-methoxybenzyl units allowed C−H⋅⋅⋅π, C−H⋅⋅⋅O interactions and PILO (interaction energy=−11.56 kcal/mol). The number of the contact fragments in the environment of the tetralin unit was larger, but the 4-methoxybenzyl unit had greater contribution to the total stabilization. The statistical analysis of the data from the Cambridge Structural Database (CSD) showed that this is a general trend. The compound is a potential inhibitor of kinase enzymes and antigen protein-coupled receptors. A correlation between the docking study and the results of the CSD analysis can be drawn. Due to a greater flexibility, the 4-methoxybenzyl unit is more adaptable for interactions with the biological targets than the tetralin unit.",
publisher = "John Wiley and Sons Inc.",
journal = "ChemPlusChem",
title = "Self-Assembly and Biorecognition of a Spirohydantoin Derived from α-Tetralone: Interplay between Chirality and Intermolecular Interactions",
volume = "85",
number = "6",
pages = "1220-1232",
doi = "10.1002/cplu.202000273"
}

Lazić, A. M., Đorđević, I., Radovanović, L., Popović, D., Rogan, J. R., Janjić, G.,& Trišović, N.. (2020). Self-Assembly and Biorecognition of a Spirohydantoin Derived from α-Tetralone: Interplay between Chirality and Intermolecular Interactions. in ChemPlusChem
John Wiley and Sons Inc.., 85(6), 1220-1232.
https://doi.org/10.1002/cplu.202000273

Lazić AM, Đorđević I, Radovanović L, Popović D, Rogan JR, Janjić G, Trišović N. Self-Assembly and Biorecognition of a Spirohydantoin Derived from α-Tetralone: Interplay between Chirality and Intermolecular Interactions. in ChemPlusChem. 2020;85(6):1220-1232.
doi:10.1002/cplu.202000273 .

Lazić, Anita M., Đorđević, Ivana, Radovanović, Lidija, Popović, Dragan, Rogan, Jelena R., Janjić, Goran, Trišović, Nemanja, "Self-Assembly and Biorecognition of a Spirohydantoin Derived from α-Tetralone: Interplay between Chirality and Intermolecular Interactions" in ChemPlusChem, 85, no. 6 (2020):1220-1232,
https://doi.org/10.1002/cplu.202000273 . .

TY  - CONF
AU  - Đorđević, Ivana
AU  - Janjić, Goran
AU  - Lazić, Anita
AU  - Gak, Kristina
AU  - Valentić, Nataša
AU  - Trišović, Nemanja
AU  - Radovanović, Lidija
AU  - Rogan, Jelena
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7541
AB  - Nekovalentne interakcije imaju značajnu ulogu u formiranju supramolekulskogkristalnog pakovanja molekula. Interakcije koje uključuju atome halogena obezbeđujuslabo, ali visoko usmerenu kontrolu pakovanja molekula u čvrstom stanju. UvođenjeF-atoma može dovesti do značajnih promena u 2D ili 3D strukturama [1], povećanjastabilnosti biomolekula [2] ili poboljšanja dizajna lekova [3]. Da bi se ispitao efekatsupstitucije H-atoma F-atomom, sintetisana su i strukturno okarakterisana dva derivatahidantoina: C15H16N2O3 (1) i C15H15N2O3F (2) (slika).Analiza kristalnih pakovanja 1 i 2 pokazala je da suNH…O i CH…O vodonične veze najbrojnije. U strukturi2 se zbog fluorovanja povećava broj interakcijacikloheksilnog (Ch) i fenil-grupe (Ph) prstena (CH…πinterakcije), kao i između dva Ph prstena (π-πinterakcije). Kvantno-hemijski proračuni na modelsistemima koji predstavljaju dimere derivata hidantoinai izolovanih cikličnih jedinjenja, pokazali su dafluorovanje utiče na stvaranje jačih CH…π i π-πinterakcija. Atom F u 2 učestvuje u formiranju triCH…F i jedne F…F interakcije, što je u saglasnosti sarezultatima Kembridžke baze podataka, koji su pokazalida su najbrojnije CH…F i F…F interakcije, a njihovajačina dostiže vrednost 2 kcal∙mol–1.Kristalogafski podaci: 1, P–1, a = 6,3079(13),b = 10,573(2), c = 11,415(2) Å, α = 67,21(3), β = 78,84(3),γ = 76,16(3)°, R1 = 6,06%; 2, P–1, a = 5,9981(12), b =11,148(2), c = 12,073(2) Å, α = 108,98(3), β = 101,57(3),γ = 105,27(3)°, R1 = 4,82%.
AB  - Non-covalent interactions have a significant role in supramolecular crystal packingsof the molecules. Halogen interactions provide weak but highly directed control of thepacking of molecules in the solid state. Introduction of F atom can leads to significantdifferences in 2D or 3D structures [1], higher structural stability of biomolecules [2] orimprove drug design [3]. In order to examine the substitution effect of H atom with Fatom, two hydantoin derivatives were synthesized and structurally characterized:C15H16N2O3 (1) i C15H15N2O3F (2) (Figure).Crystallographic analysis of 1 and 2 showed thatNH…O and CH…O hydrogen bonds are the most numerousin their crystal packings. Due to fluoridation in 2, the number of interactions among cyclohexyl (Ch) and phenyl ring(Ph) rings (CH…π interactions), as well as among two Phrings (π-π interactions) is increased. Quantum-chemicalcalculations on the model systems presented by dimmersof hydantoin derivatives and isolated cyclic compounds,verified that fluoridation caused the formation of strongerCH…π and π-π interactions. The F atom in 2 is involved inthree CH…F and one F…F interactions, which is in agreement with the results from the Cambridge Structural Database, which have shown that CH…F and F…F interactionsare the most numerous, and their strength reaches the valueof 2 kcal∙mol–1.Crystallographic data: 1, P–1, a = 6.3079(13),b = 10.573(2), c = 11.415(2) Å, α = 67.21(3), β = 78.84(3),γ = 76.16(3)°, R1 = 6.06%; 2, P–1, a = 5.9981(12),b = 11.148(2), c = 12.073(2) Å, α = 108.98(3), β = 101.57(3), γ = 105.27(3)°, R1 = 4.82%.
PB  - Beograd : Srpsko kristalografsko društvo
C3  - Izvodi radova / XXVI konferencija Srpskog kristalografskog društva, Srebrno jezero, 27–28. jun 2019
T1  - Uloga nekovalentnih interakcija fluora u pakovanju motiva: analiza kristalografskih podataka i kvantno-hemijski proračuni
T1  - The role of non-covalent fluorine interactions in packing motifs: crystallographic data analysis and quantum chemical calculations
SP  - 38
EP  - 39
UR  - https://hdl.handle.net/21.15107/rcub_cer_7541
ER  - 

@conference{
author = "Đorđević, Ivana and Janjić, Goran and Lazić, Anita and Gak, Kristina and Valentić, Nataša and Trišović, Nemanja and Radovanović, Lidija and Rogan, Jelena",
year = "2019",
abstract = "Nekovalentne interakcije imaju značajnu ulogu u formiranju supramolekulskogkristalnog pakovanja molekula. Interakcije koje uključuju atome halogena obezbeđujuslabo, ali visoko usmerenu kontrolu pakovanja molekula u čvrstom stanju. UvođenjeF-atoma može dovesti do značajnih promena u 2D ili 3D strukturama [1], povećanjastabilnosti biomolekula [2] ili poboljšanja dizajna lekova [3]. Da bi se ispitao efekatsupstitucije H-atoma F-atomom, sintetisana su i strukturno okarakterisana dva derivatahidantoina: C15H16N2O3 (1) i C15H15N2O3F (2) (slika).Analiza kristalnih pakovanja 1 i 2 pokazala je da suNH…O i CH…O vodonične veze najbrojnije. U strukturi2 se zbog fluorovanja povećava broj interakcijacikloheksilnog (Ch) i fenil-grupe (Ph) prstena (CH…πinterakcije), kao i između dva Ph prstena (π-πinterakcije). Kvantno-hemijski proračuni na modelsistemima koji predstavljaju dimere derivata hidantoinai izolovanih cikličnih jedinjenja, pokazali su dafluorovanje utiče na stvaranje jačih CH…π i π-πinterakcija. Atom F u 2 učestvuje u formiranju triCH…F i jedne F…F interakcije, što je u saglasnosti sarezultatima Kembridžke baze podataka, koji su pokazalida su najbrojnije CH…F i F…F interakcije, a njihovajačina dostiže vrednost 2 kcal∙mol–1.Kristalogafski podaci: 1, P–1, a = 6,3079(13),b = 10,573(2), c = 11,415(2) Å, α = 67,21(3), β = 78,84(3),γ = 76,16(3)°, R1 = 6,06%; 2, P–1, a = 5,9981(12), b =11,148(2), c = 12,073(2) Å, α = 108,98(3), β = 101,57(3),γ = 105,27(3)°, R1 = 4,82%., Non-covalent interactions have a significant role in supramolecular crystal packingsof the molecules. Halogen interactions provide weak but highly directed control of thepacking of molecules in the solid state. Introduction of F atom can leads to significantdifferences in 2D or 3D structures [1], higher structural stability of biomolecules [2] orimprove drug design [3]. In order to examine the substitution effect of H atom with Fatom, two hydantoin derivatives were synthesized and structurally characterized:C15H16N2O3 (1) i C15H15N2O3F (2) (Figure).Crystallographic analysis of 1 and 2 showed thatNH…O and CH…O hydrogen bonds are the most numerousin their crystal packings. Due to fluoridation in 2, the number of interactions among cyclohexyl (Ch) and phenyl ring(Ph) rings (CH…π interactions), as well as among two Phrings (π-π interactions) is increased. Quantum-chemicalcalculations on the model systems presented by dimmersof hydantoin derivatives and isolated cyclic compounds,verified that fluoridation caused the formation of strongerCH…π and π-π interactions. The F atom in 2 is involved inthree CH…F and one F…F interactions, which is in agreement with the results from the Cambridge Structural Database, which have shown that CH…F and F…F interactionsare the most numerous, and their strength reaches the valueof 2 kcal∙mol–1.Crystallographic data: 1, P–1, a = 6.3079(13),b = 10.573(2), c = 11.415(2) Å, α = 67.21(3), β = 78.84(3),γ = 76.16(3)°, R1 = 6.06%; 2, P–1, a = 5.9981(12),b = 11.148(2), c = 12.073(2) Å, α = 108.98(3), β = 101.57(3), γ = 105.27(3)°, R1 = 4.82%.",
publisher = "Beograd : Srpsko kristalografsko društvo",
journal = "Izvodi radova / XXVI konferencija Srpskog kristalografskog društva, Srebrno jezero, 27–28. jun 2019",
title = "Uloga nekovalentnih interakcija fluora u pakovanju motiva: analiza kristalografskih podataka i kvantno-hemijski proračuni, The role of non-covalent fluorine interactions in packing motifs: crystallographic data analysis and quantum chemical calculations",
pages = "38-39",
url = "https://hdl.handle.net/21.15107/rcub_cer_7541"
}

Đorđević, I., Janjić, G., Lazić, A., Gak, K., Valentić, N., Trišović, N., Radovanović, L.,& Rogan, J.. (2019). Uloga nekovalentnih interakcija fluora u pakovanju motiva: analiza kristalografskih podataka i kvantno-hemijski proračuni. in Izvodi radova / XXVI konferencija Srpskog kristalografskog društva, Srebrno jezero, 27–28. jun 2019
Beograd : Srpsko kristalografsko društvo., 38-39.
https://hdl.handle.net/21.15107/rcub_cer_7541

Đorđević I, Janjić G, Lazić A, Gak K, Valentić N, Trišović N, Radovanović L, Rogan J. Uloga nekovalentnih interakcija fluora u pakovanju motiva: analiza kristalografskih podataka i kvantno-hemijski proračuni. in Izvodi radova / XXVI konferencija Srpskog kristalografskog društva, Srebrno jezero, 27–28. jun 2019. 2019;:38-39.
https://hdl.handle.net/21.15107/rcub_cer_7541 .

Đorđević, Ivana, Janjić, Goran, Lazić, Anita, Gak, Kristina, Valentić, Nataša, Trišović, Nemanja, Radovanović, Lidija, Rogan, Jelena, "Uloga nekovalentnih interakcija fluora u pakovanju motiva: analiza kristalografskih podataka i kvantno-hemijski proračuni" in Izvodi radova / XXVI konferencija Srpskog kristalografskog društva, Srebrno jezero, 27–28. jun 2019 (2019):38-39,
https://hdl.handle.net/21.15107/rcub_cer_7541 .

TY  - JOUR
AU  - Jegdić, Bore
AU  - Bobić, Biljana
AU  - Radojković, Bojana
AU  - Alić, Behar
AU  - Radovanović, Lidija D.
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2498
AB  - This paper considers the influence of nitrogen in the shielding gas during TIG welding as well as the influence of a welding current level on the resistance to pitting corrosion and intergranular corrosion in welded joints of X5CrNi18-10 stainless steel. Testing of pitting corrosion was carried out using the potentiodynamic method, while intergranular corrosion was tested with the Double-Loop Electrochemical Potentiokinetic Reactivation method. Pitting corrosion resistance of welded joints (the weld metal and the heat affected zone) is higher in the presence of nitrogen in the shielding gas, while integranular corrosion resistance remains unchanged. Pitting corrosion resistance of the heat affected zone in the welded joint formed in nitrogen-free shielding gas is lower than in the base metal, while the weld metal has similar pitting corrosion resistance as the base metal. With an increase in a welding current level, pitting corrosion resistance and resistance to intergranular corrosion of welded joints decrease. The passivation current density is shown to be a good indicator of pitting corrosion resistance of welded joints. Hardness values of the weld metal and the heat affected zone are slightly lower than the base metal hardness value.
PB  - Elsevier
T2  - Journal of Materials Processing Technology
T1  - Corrosion resistance of welded joints of X5CrNi18-10 stainless steel
VL  - 266
SP  - 579
EP  - 587
DO  - 10.1016/j.jmatprotec.2018.11.029
ER  - 

@article{
author = "Jegdić, Bore and Bobić, Biljana and Radojković, Bojana and Alić, Behar and Radovanović, Lidija D.",
year = "2019",
abstract = "This paper considers the influence of nitrogen in the shielding gas during TIG welding as well as the influence of a welding current level on the resistance to pitting corrosion and intergranular corrosion in welded joints of X5CrNi18-10 stainless steel. Testing of pitting corrosion was carried out using the potentiodynamic method, while intergranular corrosion was tested with the Double-Loop Electrochemical Potentiokinetic Reactivation method. Pitting corrosion resistance of welded joints (the weld metal and the heat affected zone) is higher in the presence of nitrogen in the shielding gas, while integranular corrosion resistance remains unchanged. Pitting corrosion resistance of the heat affected zone in the welded joint formed in nitrogen-free shielding gas is lower than in the base metal, while the weld metal has similar pitting corrosion resistance as the base metal. With an increase in a welding current level, pitting corrosion resistance and resistance to intergranular corrosion of welded joints decrease. The passivation current density is shown to be a good indicator of pitting corrosion resistance of welded joints. Hardness values of the weld metal and the heat affected zone are slightly lower than the base metal hardness value.",
publisher = "Elsevier",
journal = "Journal of Materials Processing Technology",
title = "Corrosion resistance of welded joints of X5CrNi18-10 stainless steel",
volume = "266",
pages = "579-587",
doi = "10.1016/j.jmatprotec.2018.11.029"
}

Jegdić, B., Bobić, B., Radojković, B., Alić, B.,& Radovanović, L. D.. (2019). Corrosion resistance of welded joints of X5CrNi18-10 stainless steel. in Journal of Materials Processing Technology
Elsevier., 266, 579-587.
https://doi.org/10.1016/j.jmatprotec.2018.11.029

Jegdić B, Bobić B, Radojković B, Alić B, Radovanović LD. Corrosion resistance of welded joints of X5CrNi18-10 stainless steel. in Journal of Materials Processing Technology. 2019;266:579-587.
doi:10.1016/j.jmatprotec.2018.11.029 .

Jegdić, Bore, Bobić, Biljana, Radojković, Bojana, Alić, Behar, Radovanović, Lidija D., "Corrosion resistance of welded joints of X5CrNi18-10 stainless steel" in Journal of Materials Processing Technology, 266 (2019):579-587,
https://doi.org/10.1016/j.jmatprotec.2018.11.029 . .

TY  - JOUR
AU  - Trišović, Nemanja
AU  - Radovanović, Lidija
AU  - Janjić, Goran
AU  - Jelić, Stefan
AU  - Rogan, Jelena R.
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3277
AB  - A series of five derivatives of the anticonvulsant drug phenytoin was synthesized, and their crystal structures were determined. The relationship between the molecular and crystal structure of the investigated compounds was rationalized in the context of contribution of intermolecular interactions and supramolecular structural motifs. The conformational preferences were analyzed by comparing the rotational freedom of the phenyl groups in the investigated compounds with 5,5-diphenylhydantoins from the Cambridge Structural Database. With the exception of compound 3 bearing the cyclopropyl group, the crystal packing of the investigated compounds contains centrosymmetric dimers linked by paired N–H···O hydrogen bonds, which further self-organize through pairs of C–H···O interactions and a parallel interaction of two phenyl rings at a large offset into chains running along the c-axis. The principal feature of the crystal structure of compound 3 is formation of the chains by N–H···O hydrogen bonds and C–H···O and C–H···π interactions. The coordination of phenytoin enables more rotational freedom for the phenyl groups. An emphasis was placed on docking of the investigated compounds into the voltage-gated ion channel in the open and closed state. The obtained results indicate that hydrogen bonding and hydrophobic interactions are dominant in stabilizing energetically favored orientations of the investigated compounds bound to the protein.
PB  - American Chemical Society (ACS)
T2  - Crystal Growth & Design
T1  - Substituent Effects on the Patterns of Intermolecular Interactions of 3-Alkyl and 3-Cycloalkyl Derivatives of Phenytoin: A Crystallographic and Quantum-Chemical Study
VL  - 19
IS  - 4
SP  - 2163
EP  - 2174
DO  - 10.1021/acs.cgd.8b01776
ER  - 

@article{
author = "Trišović, Nemanja and Radovanović, Lidija and Janjić, Goran and Jelić, Stefan and Rogan, Jelena R.",
year = "2019",
abstract = "A series of five derivatives of the anticonvulsant drug phenytoin was synthesized, and their crystal structures were determined. The relationship between the molecular and crystal structure of the investigated compounds was rationalized in the context of contribution of intermolecular interactions and supramolecular structural motifs. The conformational preferences were analyzed by comparing the rotational freedom of the phenyl groups in the investigated compounds with 5,5-diphenylhydantoins from the Cambridge Structural Database. With the exception of compound 3 bearing the cyclopropyl group, the crystal packing of the investigated compounds contains centrosymmetric dimers linked by paired N–H···O hydrogen bonds, which further self-organize through pairs of C–H···O interactions and a parallel interaction of two phenyl rings at a large offset into chains running along the c-axis. The principal feature of the crystal structure of compound 3 is formation of the chains by N–H···O hydrogen bonds and C–H···O and C–H···π interactions. The coordination of phenytoin enables more rotational freedom for the phenyl groups. An emphasis was placed on docking of the investigated compounds into the voltage-gated ion channel in the open and closed state. The obtained results indicate that hydrogen bonding and hydrophobic interactions are dominant in stabilizing energetically favored orientations of the investigated compounds bound to the protein.",
publisher = "American Chemical Society (ACS)",
journal = "Crystal Growth & Design",
title = "Substituent Effects on the Patterns of Intermolecular Interactions of 3-Alkyl and 3-Cycloalkyl Derivatives of Phenytoin: A Crystallographic and Quantum-Chemical Study",
volume = "19",
number = "4",
pages = "2163-2174",
doi = "10.1021/acs.cgd.8b01776"
}

Trišović, N., Radovanović, L., Janjić, G., Jelić, S.,& Rogan, J. R.. (2019). Substituent Effects on the Patterns of Intermolecular Interactions of 3-Alkyl and 3-Cycloalkyl Derivatives of Phenytoin: A Crystallographic and Quantum-Chemical Study. in Crystal Growth & Design
American Chemical Society (ACS)., 19(4), 2163-2174.
https://doi.org/10.1021/acs.cgd.8b01776

Trišović N, Radovanović L, Janjić G, Jelić S, Rogan JR. Substituent Effects on the Patterns of Intermolecular Interactions of 3-Alkyl and 3-Cycloalkyl Derivatives of Phenytoin: A Crystallographic and Quantum-Chemical Study. in Crystal Growth & Design. 2019;19(4):2163-2174.
doi:10.1021/acs.cgd.8b01776 .

Trišović, Nemanja, Radovanović, Lidija, Janjić, Goran, Jelić, Stefan, Rogan, Jelena R., "Substituent Effects on the Patterns of Intermolecular Interactions of 3-Alkyl and 3-Cycloalkyl Derivatives of Phenytoin: A Crystallographic and Quantum-Chemical Study" in Crystal Growth & Design, 19, no. 4 (2019):2163-2174,
https://doi.org/10.1021/acs.cgd.8b01776 . .

TY  - JOUR
AU  - Trišović, Nemanja
AU  - Radovanović, Lidija
AU  - Janjić, Goran
AU  - Jelić, Stefan
AU  - Rogan, Jelena R.
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3278
AB  - A series of five derivatives of the anticonvulsant drug phenytoin was synthesized, and their crystal structures were determined. The relationship between the molecular and crystal structure of the investigated compounds was rationalized in the context of contribution of intermolecular interactions and supramolecular structural motifs. The conformational preferences were analyzed by comparing the rotational freedom of the phenyl groups in the investigated compounds with 5,5-diphenylhydantoins from the Cambridge Structural Database. With the exception of compound 3 bearing the cyclopropyl group, the crystal packing of the investigated compounds contains centrosymmetric dimers linked by paired N–H···O hydrogen bonds, which further self-organize through pairs of C–H···O interactions and a parallel interaction of two phenyl rings at a large offset into chains running along the c-axis. The principal feature of the crystal structure of compound 3 is formation of the chains by N–H···O hydrogen bonds and C–H···O and C–H···π interactions. The coordination of phenytoin enables more rotational freedom for the phenyl groups. An emphasis was placed on docking of the investigated compounds into the voltage-gated ion channel in the open and closed state. The obtained results indicate that hydrogen bonding and hydrophobic interactions are dominant in stabilizing energetically favored orientations of the investigated compounds bound to the protein.
PB  - American Chemical Society (ACS)
T2  - Crystal Growth & Design
T1  - Substituent Effects on the Patterns of Intermolecular Interactions of 3-Alkyl and 3-Cycloalkyl Derivatives of Phenytoin: A Crystallographic and Quantum-Chemical Study
VL  - 19
IS  - 4
SP  - 2163
EP  - 2174
DO  - 10.1021/acs.cgd.8b01776
ER  - 

@article{
author = "Trišović, Nemanja and Radovanović, Lidija and Janjić, Goran and Jelić, Stefan and Rogan, Jelena R.",
year = "2019",
abstract = "A series of five derivatives of the anticonvulsant drug phenytoin was synthesized, and their crystal structures were determined. The relationship between the molecular and crystal structure of the investigated compounds was rationalized in the context of contribution of intermolecular interactions and supramolecular structural motifs. The conformational preferences were analyzed by comparing the rotational freedom of the phenyl groups in the investigated compounds with 5,5-diphenylhydantoins from the Cambridge Structural Database. With the exception of compound 3 bearing the cyclopropyl group, the crystal packing of the investigated compounds contains centrosymmetric dimers linked by paired N–H···O hydrogen bonds, which further self-organize through pairs of C–H···O interactions and a parallel interaction of two phenyl rings at a large offset into chains running along the c-axis. The principal feature of the crystal structure of compound 3 is formation of the chains by N–H···O hydrogen bonds and C–H···O and C–H···π interactions. The coordination of phenytoin enables more rotational freedom for the phenyl groups. An emphasis was placed on docking of the investigated compounds into the voltage-gated ion channel in the open and closed state. The obtained results indicate that hydrogen bonding and hydrophobic interactions are dominant in stabilizing energetically favored orientations of the investigated compounds bound to the protein.",
publisher = "American Chemical Society (ACS)",
journal = "Crystal Growth & Design",
title = "Substituent Effects on the Patterns of Intermolecular Interactions of 3-Alkyl and 3-Cycloalkyl Derivatives of Phenytoin: A Crystallographic and Quantum-Chemical Study",
volume = "19",
number = "4",
pages = "2163-2174",
doi = "10.1021/acs.cgd.8b01776"
}

Trišović, N., Radovanović, L., Janjić, G., Jelić, S.,& Rogan, J. R.. (2019). Substituent Effects on the Patterns of Intermolecular Interactions of 3-Alkyl and 3-Cycloalkyl Derivatives of Phenytoin: A Crystallographic and Quantum-Chemical Study. in Crystal Growth & Design
American Chemical Society (ACS)., 19(4), 2163-2174.
https://doi.org/10.1021/acs.cgd.8b01776

Trišović N, Radovanović L, Janjić G, Jelić S, Rogan JR. Substituent Effects on the Patterns of Intermolecular Interactions of 3-Alkyl and 3-Cycloalkyl Derivatives of Phenytoin: A Crystallographic and Quantum-Chemical Study. in Crystal Growth & Design. 2019;19(4):2163-2174.
doi:10.1021/acs.cgd.8b01776 .

Trišović, Nemanja, Radovanović, Lidija, Janjić, Goran, Jelić, Stefan, Rogan, Jelena R., "Substituent Effects on the Patterns of Intermolecular Interactions of 3-Alkyl and 3-Cycloalkyl Derivatives of Phenytoin: A Crystallographic and Quantum-Chemical Study" in Crystal Growth & Design, 19, no. 4 (2019):2163-2174,
https://doi.org/10.1021/acs.cgd.8b01776 . .

TY  - JOUR
AU  - Lazić, Anita M.
AU  - Radovanović, Lidija D.
AU  - Božić, Bojan
AU  - Božić, Nedeljković B.
AU  - Vitnik, Vesna
AU  - Vitnik, Željko
AU  - Rogan, Jelena R.
AU  - Valentić, Nataša V.
AU  - Ušćumlić, Gordana
AU  - Trišović, Nemanja
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2489
AB  - Two series of cycloalkanespiro-5-hydantoins, namely cyclohexanespiro-5-hydantoins and cycloheptanespiro-5-hydantoins with a 4-substituted benzyl or a 2-(4-substituted phenyl)-2-oxoethyl group at N3 position, were synthesized and their effects on proliferation of human colon (HCT-116), leukemia (K562) and breast (MDA-MB-231) cancer cell lines were tested. For comparison, we also described the 5,5-diphenylhydantoin analogues. The structural features of the investigated compounds were characterized by elemental analysis, FT-IR, UV–Vis, 1H and 13C NMR spectroscopy and X-ray crystallography. Regarding their structure–activity relationships, it was shown that the substitution on the benzyl moiety with the methoxy, chloro or bromo group potentiated the antiproliferative activity relative to the parent compounds, while an increase in the size of the cycloalkyl group resulted mostly in a decrease of the antiproliferative activity. The single crystal X-ray analysis revealed the existence of dimers and chains formed by the N–H⋯O hydrogen bonds. The analysis of the molecular descriptors of Lipinski demonstrated that all investigated compounds obeyed the rule of five. To further understand their geometry and electronic structure, DFT calculations with B3LYP method using 6-311++G(d,p) basic set were performed. In this context, the UV–Vis spectra of the investigated compounds were analyzed in detail, whereby the predicted absorption spectra from DFT calculation matched the experimentally obtained ones, with a good correlation. The interesting physico-chemical and pharmacologically relevant properties of the investigated compounds warrant their further investigation.
PB  - Elsevier
T2  - Journal of Molecular Structure
T1  - Synthesis, structural characterization, DFT calculations and antiproliferative evaluation of novel spirohydantoin derivatives containing a substituted benzyl moiety
VL  - 1180
SP  - 48
EP  - 62
DO  - 10.1016/j.molstruc.2018.11.071
ER  - 

@article{
author = "Lazić, Anita M. and Radovanović, Lidija D. and Božić, Bojan and Božić, Nedeljković B. and Vitnik, Vesna and Vitnik, Željko and Rogan, Jelena R. and Valentić, Nataša V. and Ušćumlić, Gordana and Trišović, Nemanja",
year = "2019",
abstract = "Two series of cycloalkanespiro-5-hydantoins, namely cyclohexanespiro-5-hydantoins and cycloheptanespiro-5-hydantoins with a 4-substituted benzyl or a 2-(4-substituted phenyl)-2-oxoethyl group at N3 position, were synthesized and their effects on proliferation of human colon (HCT-116), leukemia (K562) and breast (MDA-MB-231) cancer cell lines were tested. For comparison, we also described the 5,5-diphenylhydantoin analogues. The structural features of the investigated compounds were characterized by elemental analysis, FT-IR, UV–Vis, 1H and 13C NMR spectroscopy and X-ray crystallography. Regarding their structure–activity relationships, it was shown that the substitution on the benzyl moiety with the methoxy, chloro or bromo group potentiated the antiproliferative activity relative to the parent compounds, while an increase in the size of the cycloalkyl group resulted mostly in a decrease of the antiproliferative activity. The single crystal X-ray analysis revealed the existence of dimers and chains formed by the N–H⋯O hydrogen bonds. The analysis of the molecular descriptors of Lipinski demonstrated that all investigated compounds obeyed the rule of five. To further understand their geometry and electronic structure, DFT calculations with B3LYP method using 6-311++G(d,p) basic set were performed. In this context, the UV–Vis spectra of the investigated compounds were analyzed in detail, whereby the predicted absorption spectra from DFT calculation matched the experimentally obtained ones, with a good correlation. The interesting physico-chemical and pharmacologically relevant properties of the investigated compounds warrant their further investigation.",
publisher = "Elsevier",
journal = "Journal of Molecular Structure",
title = "Synthesis, structural characterization, DFT calculations and antiproliferative evaluation of novel spirohydantoin derivatives containing a substituted benzyl moiety",
volume = "1180",
pages = "48-62",
doi = "10.1016/j.molstruc.2018.11.071"
}

Lazić, A. M., Radovanović, L. D., Božić, B., Božić, N. B., Vitnik, V., Vitnik, Ž., Rogan, J. R., Valentić, N. V., Ušćumlić, G.,& Trišović, N.. (2019). Synthesis, structural characterization, DFT calculations and antiproliferative evaluation of novel spirohydantoin derivatives containing a substituted benzyl moiety. in Journal of Molecular Structure
Elsevier., 1180, 48-62.
https://doi.org/10.1016/j.molstruc.2018.11.071

Lazić AM, Radovanović LD, Božić B, Božić NB, Vitnik V, Vitnik Ž, Rogan JR, Valentić NV, Ušćumlić G, Trišović N. Synthesis, structural characterization, DFT calculations and antiproliferative evaluation of novel spirohydantoin derivatives containing a substituted benzyl moiety. in Journal of Molecular Structure. 2019;1180:48-62.
doi:10.1016/j.molstruc.2018.11.071 .

Lazić, Anita M., Radovanović, Lidija D., Božić, Bojan, Božić, Nedeljković B., Vitnik, Vesna, Vitnik, Željko, Rogan, Jelena R., Valentić, Nataša V., Ušćumlić, Gordana, Trišović, Nemanja, "Synthesis, structural characterization, DFT calculations and antiproliferative evaluation of novel spirohydantoin derivatives containing a substituted benzyl moiety" in Journal of Molecular Structure, 1180 (2019):48-62,
https://doi.org/10.1016/j.molstruc.2018.11.071 . .

TY  - JOUR
AU  - Lazić, Anita M.
AU  - Radovanović, Lidija D.
AU  - Božić, Bojan
AU  - Božić, Nedeljković B.
AU  - Vitnik, Vesna
AU  - Vitnik, Željko
AU  - Rogan, Jelena R.
AU  - Valentić, Nataša V.
AU  - Ušćumlić, Gordana
AU  - Trišović, Nemanja
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2906
AB  - Two series of cycloalkanespiro-5-hydantoins, namely cyclohexanespiro-5-hydantoins and cycloheptanespiro-5-hydantoins with a 4-substituted benzyl or a 2-(4-substituted phenyl)-2-oxoethyl group at N3 position, were synthesized and their effects on proliferation of human colon (HCT-116), leukemia (K562) and breast (MDA-MB-231) cancer cell lines were tested. For comparison, we also described the 5,5-diphenylhydantoin analogues. The structural features of the investigated compounds were characterized by elemental analysis, FT-IR, UV–Vis, 1H and 13C NMR spectroscopy and X-ray crystallography. Regarding their structure–activity relationships, it was shown that the substitution on the benzyl moiety with the methoxy, chloro or bromo group potentiated the antiproliferative activity relative to the parent compounds, while an increase in the size of the cycloalkyl group resulted mostly in a decrease of the antiproliferative activity. The single crystal X-ray analysis revealed the existence of dimers and chains formed by the N–H⋯O hydrogen bonds. The analysis of the molecular descriptors of Lipinski demonstrated that all investigated compounds obeyed the rule of five. To further understand their geometry and electronic structure, DFT calculations with B3LYP method using 6-311++G(d,p) basic set were performed. In this context, the UV–Vis spectra of the investigated compounds were analyzed in detail, whereby the predicted absorption spectra from DFT calculation matched the experimentally obtained ones, with a good correlation. The interesting physico-chemical and pharmacologically relevant properties of the investigated compounds warrant their further investigation.
PB  - Elsevier
T2  - Journal of Molecular Structure
T1  - Synthesis, structural characterization, DFT calculations and antiproliferative evaluation of novel spirohydantoin derivatives containing a substituted benzyl moiety
VL  - 1180
SP  - 48
EP  - 62
DO  - 10.1016/j.molstruc.2018.11.071
ER  - 

@article{
author = "Lazić, Anita M. and Radovanović, Lidija D. and Božić, Bojan and Božić, Nedeljković B. and Vitnik, Vesna and Vitnik, Željko and Rogan, Jelena R. and Valentić, Nataša V. and Ušćumlić, Gordana and Trišović, Nemanja",
year = "2019",
abstract = "Two series of cycloalkanespiro-5-hydantoins, namely cyclohexanespiro-5-hydantoins and cycloheptanespiro-5-hydantoins with a 4-substituted benzyl or a 2-(4-substituted phenyl)-2-oxoethyl group at N3 position, were synthesized and their effects on proliferation of human colon (HCT-116), leukemia (K562) and breast (MDA-MB-231) cancer cell lines were tested. For comparison, we also described the 5,5-diphenylhydantoin analogues. The structural features of the investigated compounds were characterized by elemental analysis, FT-IR, UV–Vis, 1H and 13C NMR spectroscopy and X-ray crystallography. Regarding their structure–activity relationships, it was shown that the substitution on the benzyl moiety with the methoxy, chloro or bromo group potentiated the antiproliferative activity relative to the parent compounds, while an increase in the size of the cycloalkyl group resulted mostly in a decrease of the antiproliferative activity. The single crystal X-ray analysis revealed the existence of dimers and chains formed by the N–H⋯O hydrogen bonds. The analysis of the molecular descriptors of Lipinski demonstrated that all investigated compounds obeyed the rule of five. To further understand their geometry and electronic structure, DFT calculations with B3LYP method using 6-311++G(d,p) basic set were performed. In this context, the UV–Vis spectra of the investigated compounds were analyzed in detail, whereby the predicted absorption spectra from DFT calculation matched the experimentally obtained ones, with a good correlation. The interesting physico-chemical and pharmacologically relevant properties of the investigated compounds warrant their further investigation.",
publisher = "Elsevier",
journal = "Journal of Molecular Structure",
title = "Synthesis, structural characterization, DFT calculations and antiproliferative evaluation of novel spirohydantoin derivatives containing a substituted benzyl moiety",
volume = "1180",
pages = "48-62",
doi = "10.1016/j.molstruc.2018.11.071"
}

Lazić, A. M., Radovanović, L. D., Božić, B., Božić, N. B., Vitnik, V., Vitnik, Ž., Rogan, J. R., Valentić, N. V., Ušćumlić, G.,& Trišović, N.. (2019). Synthesis, structural characterization, DFT calculations and antiproliferative evaluation of novel spirohydantoin derivatives containing a substituted benzyl moiety. in Journal of Molecular Structure
Elsevier., 1180, 48-62.
https://doi.org/10.1016/j.molstruc.2018.11.071

Lazić AM, Radovanović LD, Božić B, Božić NB, Vitnik V, Vitnik Ž, Rogan JR, Valentić NV, Ušćumlić G, Trišović N. Synthesis, structural characterization, DFT calculations and antiproliferative evaluation of novel spirohydantoin derivatives containing a substituted benzyl moiety. in Journal of Molecular Structure. 2019;1180:48-62.
doi:10.1016/j.molstruc.2018.11.071 .

Lazić, Anita M., Radovanović, Lidija D., Božić, Bojan, Božić, Nedeljković B., Vitnik, Vesna, Vitnik, Željko, Rogan, Jelena R., Valentić, Nataša V., Ušćumlić, Gordana, Trišović, Nemanja, "Synthesis, structural characterization, DFT calculations and antiproliferative evaluation of novel spirohydantoin derivatives containing a substituted benzyl moiety" in Journal of Molecular Structure, 1180 (2019):48-62,
https://doi.org/10.1016/j.molstruc.2018.11.071 . .

TY  - JOUR
AU  - Lazić, Anita M.
AU  - Božić, Bojan
AU  - Vitnik, Vesna
AU  - Vitnik, Željko
AU  - Rogan, Jelena R.
AU  - Radovanović, Lidija D.
AU  - Valentić, Nataša V.
AU  - Ušćumlić, Gordana
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2073
AB  - The structure-property relationship of newly synthesized 3-(4-substituted benzyl)-1,3-diazaspiro [4.4] nonane-2,4-diones was studied by experimental and calculated methods. The prepared compounds were characterized by UV-Vis, FT-IR, H-1 NMR and C-13 NMR spectroscopy and elemental analysis. The crystal structure was elucidated by single-crystal X-ray diffraction. The 3-benzy1-1,3-diazaspiro[4.41nonane-2,4-dione crystallizes in triclinic P-1 space group, with two crystallographically independent molecules in the asymmetric unit. Cyclopentane ring adopts an envelope conformation. A three-dimensional crystal packing is governed by hydrogen N-H center dot center dot center dot O bonds, numerous C-H center dot center dot center dot O/N and C-H center dot center dot center dot pi interactions between neighboring molecules. Density functional theory (DFT) calculations with B3LYP and M06-2X methods using 6-311++G(d,p) basis set were performed to provide structural and spectroscopic information. Comparisons between experimental and calculated UV-Vis spectral properties suggest that the monomeric form of the investigated spirohydantoins is dominant in all used solvents. The effects of substituents on the absorption spectra of spirohydantoins are interpreted by correlation of absorption frequencies with Hammett equation. The lipophilicities of the investigated molecules were estimated by calculation of their log P values. Some of the spirohydantoins synthesized in this work, exhibit the lipophilicities comparable to the standard medicine anticonvulsant drug Phenytoin. The results obtained in this investigation afford guidelines for the preparation of new derivatives of spirohydantoin as potential anticonvulsant agents and for better understanding the structure-activity relationship.
PB  - Elsevier
T2  - Journal of Molecular Structure
T1  - Structure-property relationship of 3-(4-substituted benzyl)-1,3-diazaspiro[4.4]nonane-2,4-diones as new potentional anticonvulsant agents. An experimental and theoretical study
VL  - 1127
SP  - 88
EP  - 98
DO  - 10.1016/j.molstruc.2016.07.069
ER  - 

@article{
author = "Lazić, Anita M. and Božić, Bojan and Vitnik, Vesna and Vitnik, Željko and Rogan, Jelena R. and Radovanović, Lidija D. and Valentić, Nataša V. and Ušćumlić, Gordana",
year = "2017",
abstract = "The structure-property relationship of newly synthesized 3-(4-substituted benzyl)-1,3-diazaspiro [4.4] nonane-2,4-diones was studied by experimental and calculated methods. The prepared compounds were characterized by UV-Vis, FT-IR, H-1 NMR and C-13 NMR spectroscopy and elemental analysis. The crystal structure was elucidated by single-crystal X-ray diffraction. The 3-benzy1-1,3-diazaspiro[4.41nonane-2,4-dione crystallizes in triclinic P-1 space group, with two crystallographically independent molecules in the asymmetric unit. Cyclopentane ring adopts an envelope conformation. A three-dimensional crystal packing is governed by hydrogen N-H center dot center dot center dot O bonds, numerous C-H center dot center dot center dot O/N and C-H center dot center dot center dot pi interactions between neighboring molecules. Density functional theory (DFT) calculations with B3LYP and M06-2X methods using 6-311++G(d,p) basis set were performed to provide structural and spectroscopic information. Comparisons between experimental and calculated UV-Vis spectral properties suggest that the monomeric form of the investigated spirohydantoins is dominant in all used solvents. The effects of substituents on the absorption spectra of spirohydantoins are interpreted by correlation of absorption frequencies with Hammett equation. The lipophilicities of the investigated molecules were estimated by calculation of their log P values. Some of the spirohydantoins synthesized in this work, exhibit the lipophilicities comparable to the standard medicine anticonvulsant drug Phenytoin. The results obtained in this investigation afford guidelines for the preparation of new derivatives of spirohydantoin as potential anticonvulsant agents and for better understanding the structure-activity relationship.",
publisher = "Elsevier",
journal = "Journal of Molecular Structure",
title = "Structure-property relationship of 3-(4-substituted benzyl)-1,3-diazaspiro[4.4]nonane-2,4-diones as new potentional anticonvulsant agents. An experimental and theoretical study",
volume = "1127",
pages = "88-98",
doi = "10.1016/j.molstruc.2016.07.069"
}

Lazić, A. M., Božić, B., Vitnik, V., Vitnik, Ž., Rogan, J. R., Radovanović, L. D., Valentić, N. V.,& Ušćumlić, G.. (2017). Structure-property relationship of 3-(4-substituted benzyl)-1,3-diazaspiro[4.4]nonane-2,4-diones as new potentional anticonvulsant agents. An experimental and theoretical study. in Journal of Molecular Structure
Elsevier., 1127, 88-98.
https://doi.org/10.1016/j.molstruc.2016.07.069

Lazić AM, Božić B, Vitnik V, Vitnik Ž, Rogan JR, Radovanović LD, Valentić NV, Ušćumlić G. Structure-property relationship of 3-(4-substituted benzyl)-1,3-diazaspiro[4.4]nonane-2,4-diones as new potentional anticonvulsant agents. An experimental and theoretical study. in Journal of Molecular Structure. 2017;1127:88-98.
doi:10.1016/j.molstruc.2016.07.069 .

Lazić, Anita M., Božić, Bojan, Vitnik, Vesna, Vitnik, Željko, Rogan, Jelena R., Radovanović, Lidija D., Valentić, Nataša V., Ušćumlić, Gordana, "Structure-property relationship of 3-(4-substituted benzyl)-1,3-diazaspiro[4.4]nonane-2,4-diones as new potentional anticonvulsant agents. An experimental and theoretical study" in Journal of Molecular Structure, 1127 (2017):88-98,
https://doi.org/10.1016/j.molstruc.2016.07.069 . .

TY  - JOUR
AU  - Lazić, Anita M.
AU  - Trišović, Nemanja
AU  - Radovanović, Lidija D.
AU  - Rogan, Jelena R.
AU  - Poleti, Dejan
AU  - Vitnik, Željko
AU  - Vitnik, Vesna
AU  - Ušćumlić, Gordana
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2204
AB  - A series of cycloalkane-5-spirohydantoins bearing a halogeno substituted benzyl group (X = Cl and Br) in position 3 has been synthesized and their structures (1-6) have been determined by a single crystal X-ray diffraction method. These compounds have multiple functional groups, which allow greater competition and/ or cooperation among the different intermolecular interactions in the formation of their crystal structures. The molecules are linked together by paired N-H... O hydrogen bonds in R22(8) rings, while the CH. O interactions lead to their further association into double chains. The contribution of the cycloalkyl ring depends on its conformational flexibility and the multiple C-H donor implications. In the case of compounds 1-4 bearing the cyclopentyl or the cyclohexyl ring, halogen bonding (X...O) interactions give rise to a supramolecular pseudo-hexagonal network. In addition, the C-H... X interactions with a higher degree of multifurcation at the halogen acceptor have an important role in the formation of the crystal structure. Regarding compounds 5 and 6 with the cycloheptane ring, the X. O interaction is absent, and along with the C-H. X interactions, these compounds realize an alternative crystal structure with an emphasis on the X. p interactions. The lattice energies of all these crystal structures, as well as the intermolecular pair energies, have been calculated using PIXEL and further partitioned into coulombic, dispersive, polarization and repulsive factors. The crystal structures have also been subjected to Hirshfeld surface analysis which reveals that approximately 75% of the close contacts correspond to relatively weak interactions. The application of both concepts has provided a new insight into the relationship between the molecular interactions and crystal structures of the hydantoin derivatives.
PB  - Royal Soc Chemistry, Cambridge
T2  - Crystengcomm
T1  - Towards understanding intermolecular interactions in hydantoin derivatives: the case of cycloalkane-5-spirohydantoins tethered with a halogenated benzyl moiety
VL  - 19
IS  - 3
SP  - 469
EP  - 483
DO  - 10.1039/c6ce02210c
ER  - 

@article{
author = "Lazić, Anita M. and Trišović, Nemanja and Radovanović, Lidija D. and Rogan, Jelena R. and Poleti, Dejan and Vitnik, Željko and Vitnik, Vesna and Ušćumlić, Gordana",
year = "2017",
abstract = "A series of cycloalkane-5-spirohydantoins bearing a halogeno substituted benzyl group (X = Cl and Br) in position 3 has been synthesized and their structures (1-6) have been determined by a single crystal X-ray diffraction method. These compounds have multiple functional groups, which allow greater competition and/ or cooperation among the different intermolecular interactions in the formation of their crystal structures. The molecules are linked together by paired N-H... O hydrogen bonds in R22(8) rings, while the CH. O interactions lead to their further association into double chains. The contribution of the cycloalkyl ring depends on its conformational flexibility and the multiple C-H donor implications. In the case of compounds 1-4 bearing the cyclopentyl or the cyclohexyl ring, halogen bonding (X...O) interactions give rise to a supramolecular pseudo-hexagonal network. In addition, the C-H... X interactions with a higher degree of multifurcation at the halogen acceptor have an important role in the formation of the crystal structure. Regarding compounds 5 and 6 with the cycloheptane ring, the X. O interaction is absent, and along with the C-H. X interactions, these compounds realize an alternative crystal structure with an emphasis on the X. p interactions. The lattice energies of all these crystal structures, as well as the intermolecular pair energies, have been calculated using PIXEL and further partitioned into coulombic, dispersive, polarization and repulsive factors. The crystal structures have also been subjected to Hirshfeld surface analysis which reveals that approximately 75% of the close contacts correspond to relatively weak interactions. The application of both concepts has provided a new insight into the relationship between the molecular interactions and crystal structures of the hydantoin derivatives.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Crystengcomm",
title = "Towards understanding intermolecular interactions in hydantoin derivatives: the case of cycloalkane-5-spirohydantoins tethered with a halogenated benzyl moiety",
volume = "19",
number = "3",
pages = "469-483",
doi = "10.1039/c6ce02210c"
}

Lazić, A. M., Trišović, N., Radovanović, L. D., Rogan, J. R., Poleti, D., Vitnik, Ž., Vitnik, V.,& Ušćumlić, G.. (2017). Towards understanding intermolecular interactions in hydantoin derivatives: the case of cycloalkane-5-spirohydantoins tethered with a halogenated benzyl moiety. in Crystengcomm
Royal Soc Chemistry, Cambridge., 19(3), 469-483.
https://doi.org/10.1039/c6ce02210c

Lazić AM, Trišović N, Radovanović LD, Rogan JR, Poleti D, Vitnik Ž, Vitnik V, Ušćumlić G. Towards understanding intermolecular interactions in hydantoin derivatives: the case of cycloalkane-5-spirohydantoins tethered with a halogenated benzyl moiety. in Crystengcomm. 2017;19(3):469-483.
doi:10.1039/c6ce02210c .

Lazić, Anita M., Trišović, Nemanja, Radovanović, Lidija D., Rogan, Jelena R., Poleti, Dejan, Vitnik, Željko, Vitnik, Vesna, Ušćumlić, Gordana, "Towards understanding intermolecular interactions in hydantoin derivatives: the case of cycloalkane-5-spirohydantoins tethered with a halogenated benzyl moiety" in Crystengcomm, 19, no. 3 (2017):469-483,
https://doi.org/10.1039/c6ce02210c . .

TY  - JOUR
AU  - Lazić, Anita M.
AU  - Trišović, Nemanja
AU  - Radovanović, Lidija D.
AU  - Rogan, Jelena R.
AU  - Poleti, Dejan
AU  - Vitnik, Željko
AU  - Vitnik, Vesna
AU  - Ušćumlić, Gordana
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3002
AB  - A series of cycloalkane-5-spirohydantoins bearing a halogeno substituted benzyl group (X = Cl and Br) in position 3 has been synthesized and their structures (1-6) have been determined by a single crystal X-ray diffraction method. These compounds have multiple functional groups, which allow greater competition and/ or cooperation among the different intermolecular interactions in the formation of their crystal structures. The molecules are linked together by paired N-H... O hydrogen bonds in R22(8) rings, while the CH. O interactions lead to their further association into double chains. The contribution of the cycloalkyl ring depends on its conformational flexibility and the multiple C-H donor implications. In the case of compounds 1-4 bearing the cyclopentyl or the cyclohexyl ring, halogen bonding (X...O) interactions give rise to a supramolecular pseudo-hexagonal network. In addition, the C-H... X interactions with a higher degree of multifurcation at the halogen acceptor have an important role in the formation of the crystal structure. Regarding compounds 5 and 6 with the cycloheptane ring, the X. O interaction is absent, and along with the C-H. X interactions, these compounds realize an alternative crystal structure with an emphasis on the X. p interactions. The lattice energies of all these crystal structures, as well as the intermolecular pair energies, have been calculated using PIXEL and further partitioned into coulombic, dispersive, polarization and repulsive factors. The crystal structures have also been subjected to Hirshfeld surface analysis which reveals that approximately 75% of the close contacts correspond to relatively weak interactions. The application of both concepts has provided a new insight into the relationship between the molecular interactions and crystal structures of the hydantoin derivatives.
PB  - Royal Soc Chemistry, Cambridge
T2  - CrystEngComm
T1  - Towards understanding intermolecular interactions in hydantoin derivatives: the case of cycloalkane-5-spirohydantoins tethered with a halogenated benzyl moiety
VL  - 19
IS  - 3
SP  - 469
EP  - 483
DO  - 10.1039/c6ce02210c
ER  - 

@article{
author = "Lazić, Anita M. and Trišović, Nemanja and Radovanović, Lidija D. and Rogan, Jelena R. and Poleti, Dejan and Vitnik, Željko and Vitnik, Vesna and Ušćumlić, Gordana",
year = "2017",
abstract = "A series of cycloalkane-5-spirohydantoins bearing a halogeno substituted benzyl group (X = Cl and Br) in position 3 has been synthesized and their structures (1-6) have been determined by a single crystal X-ray diffraction method. These compounds have multiple functional groups, which allow greater competition and/ or cooperation among the different intermolecular interactions in the formation of their crystal structures. The molecules are linked together by paired N-H... O hydrogen bonds in R22(8) rings, while the CH. O interactions lead to their further association into double chains. The contribution of the cycloalkyl ring depends on its conformational flexibility and the multiple C-H donor implications. In the case of compounds 1-4 bearing the cyclopentyl or the cyclohexyl ring, halogen bonding (X...O) interactions give rise to a supramolecular pseudo-hexagonal network. In addition, the C-H... X interactions with a higher degree of multifurcation at the halogen acceptor have an important role in the formation of the crystal structure. Regarding compounds 5 and 6 with the cycloheptane ring, the X. O interaction is absent, and along with the C-H. X interactions, these compounds realize an alternative crystal structure with an emphasis on the X. p interactions. The lattice energies of all these crystal structures, as well as the intermolecular pair energies, have been calculated using PIXEL and further partitioned into coulombic, dispersive, polarization and repulsive factors. The crystal structures have also been subjected to Hirshfeld surface analysis which reveals that approximately 75% of the close contacts correspond to relatively weak interactions. The application of both concepts has provided a new insight into the relationship between the molecular interactions and crystal structures of the hydantoin derivatives.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "CrystEngComm",
title = "Towards understanding intermolecular interactions in hydantoin derivatives: the case of cycloalkane-5-spirohydantoins tethered with a halogenated benzyl moiety",
volume = "19",
number = "3",
pages = "469-483",
doi = "10.1039/c6ce02210c"
}

Lazić, A. M., Trišović, N., Radovanović, L. D., Rogan, J. R., Poleti, D., Vitnik, Ž., Vitnik, V.,& Ušćumlić, G.. (2017). Towards understanding intermolecular interactions in hydantoin derivatives: the case of cycloalkane-5-spirohydantoins tethered with a halogenated benzyl moiety. in CrystEngComm
Royal Soc Chemistry, Cambridge., 19(3), 469-483.
https://doi.org/10.1039/c6ce02210c

Lazić AM, Trišović N, Radovanović LD, Rogan JR, Poleti D, Vitnik Ž, Vitnik V, Ušćumlić G. Towards understanding intermolecular interactions in hydantoin derivatives: the case of cycloalkane-5-spirohydantoins tethered with a halogenated benzyl moiety. in CrystEngComm. 2017;19(3):469-483.
doi:10.1039/c6ce02210c .

Lazić, Anita M., Trišović, Nemanja, Radovanović, Lidija D., Rogan, Jelena R., Poleti, Dejan, Vitnik, Željko, Vitnik, Vesna, Ušćumlić, Gordana, "Towards understanding intermolecular interactions in hydantoin derivatives: the case of cycloalkane-5-spirohydantoins tethered with a halogenated benzyl moiety" in CrystEngComm, 19, no. 3 (2017):469-483,
https://doi.org/10.1039/c6ce02210c . .