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  - Cvetković, J.P.
AU  - Božić, Bojan
AU  - Banjac, Nebojša R.
AU  - Petrović, J.
AU  - Soković, Marina
AU  - Vitnik, Vesna
AU  - Vitnik, Željko
AU  - Ušćumlić, Gordana
AU  - Valentić, Nataša V.
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2494
AB  - In the present study, twelve new 1-aryl-3-ethyl-3-methylpyrrolidine-2,5-diones were synthesized and their structures were characterized by FT-IR, 1H NMR, 13C NMR spectroscopy and elemental analysis. In the final step of synthetic rout, condensation between corresponding succinic acid and substituted anilines has been improved using the microwave irradiation. Significantly higher yields compared to conventional condensation have been observed. The preliminary biological results indicated that some of the synthesized compounds showed promising in vitro antifungal activities towards several test fungi. 1-(4-Bromophenyl)-3-ethyl-3-methylpyrrolidine-2,5-dione (8) exhibited significant in vitro inhibitory activities against broad spectra of fungus, and on the basis of obtained data, the investigated bromo derivative has to be observed as novel potential fungicide. The density functional theory (DFT) calculations have been performed in order to study the structure-activity relationship (SAR) of the investigated molecules. In order to prediction of the chemical activity of the molecule, the molecular electrostatic potential (MEP) map was analyzed for the optimized geometry of 1-phenyl-3-ethyl-3-methylpyrrolidine-2,5-dione (4) and 1-(4-bromophenyl)-3-ethyl-3-methylpyrrolidine-2,5-dione (8).
PB  - Elsevier
T2  - Journal of Molecular Structure
T1  - Synthesis, antimicrobial activity and quantum chemical investigation of novel succinimide derivatives
VL  - 1181
SP  - 148
EP  - 156
DO  - 10.1016/j.molstruc.2018.12.083
ER  - 

@article{
author = "Cvetković, J.P. and Božić, Bojan and Banjac, Nebojša R. and Petrović, J. and Soković, Marina and Vitnik, Vesna and Vitnik, Željko and Ušćumlić, Gordana and Valentić, Nataša V.",
year = "2019",
abstract = "In the present study, twelve new 1-aryl-3-ethyl-3-methylpyrrolidine-2,5-diones were synthesized and their structures were characterized by FT-IR, 1H NMR, 13C NMR spectroscopy and elemental analysis. In the final step of synthetic rout, condensation between corresponding succinic acid and substituted anilines has been improved using the microwave irradiation. Significantly higher yields compared to conventional condensation have been observed. The preliminary biological results indicated that some of the synthesized compounds showed promising in vitro antifungal activities towards several test fungi. 1-(4-Bromophenyl)-3-ethyl-3-methylpyrrolidine-2,5-dione (8) exhibited significant in vitro inhibitory activities against broad spectra of fungus, and on the basis of obtained data, the investigated bromo derivative has to be observed as novel potential fungicide. The density functional theory (DFT) calculations have been performed in order to study the structure-activity relationship (SAR) of the investigated molecules. In order to prediction of the chemical activity of the molecule, the molecular electrostatic potential (MEP) map was analyzed for the optimized geometry of 1-phenyl-3-ethyl-3-methylpyrrolidine-2,5-dione (4) and 1-(4-bromophenyl)-3-ethyl-3-methylpyrrolidine-2,5-dione (8).",
publisher = "Elsevier",
journal = "Journal of Molecular Structure",
title = "Synthesis, antimicrobial activity and quantum chemical investigation of novel succinimide derivatives",
volume = "1181",
pages = "148-156",
doi = "10.1016/j.molstruc.2018.12.083"
}

Cvetković, J.P., Božić, B., Banjac, N. R., Petrović, J., Soković, M., Vitnik, V., Vitnik, Ž., Ušćumlić, G.,& Valentić, N. V.. (2019). Synthesis, antimicrobial activity and quantum chemical investigation of novel succinimide derivatives. in Journal of Molecular Structure
Elsevier., 1181, 148-156.
https://doi.org/10.1016/j.molstruc.2018.12.083

Cvetković J, Božić B, Banjac NR, Petrović J, Soković M, Vitnik V, Vitnik Ž, Ušćumlić G, Valentić NV. Synthesis, antimicrobial activity and quantum chemical investigation of novel succinimide derivatives. in Journal of Molecular Structure. 2019;1181:148-156.
doi:10.1016/j.molstruc.2018.12.083 .

Cvetković, J.P., Božić, Bojan, Banjac, Nebojša R., Petrović, J., Soković, Marina, Vitnik, Vesna, Vitnik, Željko, Ušćumlić, Gordana, Valentić, Nataša V., "Synthesis, antimicrobial activity and quantum chemical investigation of novel succinimide derivatives" in Journal of Molecular Structure, 1181 (2019):148-156,
https://doi.org/10.1016/j.molstruc.2018.12.083 . .

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  - Petković Cvetković, Jelena
AU  - Božić, Bojan
AU  - Banjac, Nebojša R.
AU  - Lađarević, Jelena
AU  - Vitnik, Vesna
AU  - Vitnik, Željko
AU  - Valentić, Nataša V.
AU  - Ušćumlić, Gordana
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3206
AB  - Novel succinimide derivatives were synthesized from 3-methyl-3-phenylsuccinic acid and substituted anilines under solvent-free conditions by using microwave irradiation. All obtained compounds were characterized by ultraviolet (UV), Fourier-transform infrared (FT-IR), 1H and 13С nuclear magnetic resonance (NMR) spectroscopy as well as by elemental analysis. The influence of the substituent electronic effects on spectroscopic data was analyzed by applying the Hammett equation. Moreover, a detailed interpretation and comparison of experimentally obtained and theoretically calculated FT-IR, UV and NMR spectra was performed. Density functional theory (DFT) calculated data of the investigated succinimides were obtained and analyzed in order to determine their structural, spectroscopic and electronic properties. Furthermore, ADMET factor profiling and in-silico prediction of potential biological activities of novel succinimide derivatives have been performed.
AB  - Novi derivati sukcinimida sintetisani su polazeći od 3-metil-3-fenilćilibarne kiseline i supstituisanih analina u mikrotalasnom reaktoru u odsustvu rastvarača. Sva jedinjenja su okarakterisana primenom UV-vidljive spektroskopije, infracrvene spektroskopije sa Furijeovom transformacijom (FT-IR), protonske nuklearne magnetne rezonancije (1H NMR), nuklearne magnetne rezonancije ugljenika-13, (13С NMR), kao i elementalnom analizom. Uticaj elektronskih efekata supstituenata na spektroskopske podatke analiziran je upotrebom Hametove jednačine. Takođe, izvršena je detaljna interpretacija, kao i poređenje eksperimentalno dobijenih i teorijski izračunatih FT-IR, UV i NMR spektara. Pored toga, urađeno je ADMET (engl. absorption, distribution, metabolism, excretion and toxicity) profilisanje i in-silico predviđanje potencijalne biološke aktivnosti novosintetisanih derivata sukcinimida.
PB  - Belgrade : Association of the Chemical Engineers of Serbia
T2  - Hemijska industrija
T1  - Spectroscopic and quantum chemical elucidation of newly synthesized 1-aryl-3-methyl-3-phenylpyrrolidine-2,5-diones as potential anticonvulsant agents
VL  - 73
IS  - 2
SP  - 125
EP  - 137
DO  - 10.2298/HEMIND190214011P
ER  - 

@article{
author = "Petković Cvetković, Jelena and Božić, Bojan and Banjac, Nebojša R. and Lađarević, Jelena and Vitnik, Vesna and Vitnik, Željko and Valentić, Nataša V. and Ušćumlić, Gordana",
year = "2019",
abstract = "Novel succinimide derivatives were synthesized from 3-methyl-3-phenylsuccinic acid and substituted anilines under solvent-free conditions by using microwave irradiation. All obtained compounds were characterized by ultraviolet (UV), Fourier-transform infrared (FT-IR), 1H and 13С nuclear magnetic resonance (NMR) spectroscopy as well as by elemental analysis. The influence of the substituent electronic effects on spectroscopic data was analyzed by applying the Hammett equation. Moreover, a detailed interpretation and comparison of experimentally obtained and theoretically calculated FT-IR, UV and NMR spectra was performed. Density functional theory (DFT) calculated data of the investigated succinimides were obtained and analyzed in order to determine their structural, spectroscopic and electronic properties. Furthermore, ADMET factor profiling and in-silico prediction of potential biological activities of novel succinimide derivatives have been performed., Novi derivati sukcinimida sintetisani su polazeći od 3-metil-3-fenilćilibarne kiseline i supstituisanih analina u mikrotalasnom reaktoru u odsustvu rastvarača. Sva jedinjenja su okarakterisana primenom UV-vidljive spektroskopije, infracrvene spektroskopije sa Furijeovom transformacijom (FT-IR), protonske nuklearne magnetne rezonancije (1H NMR), nuklearne magnetne rezonancije ugljenika-13, (13С NMR), kao i elementalnom analizom. Uticaj elektronskih efekata supstituenata na spektroskopske podatke analiziran je upotrebom Hametove jednačine. Takođe, izvršena je detaljna interpretacija, kao i poređenje eksperimentalno dobijenih i teorijski izračunatih FT-IR, UV i NMR spektara. Pored toga, urađeno je ADMET (engl. absorption, distribution, metabolism, excretion and toxicity) profilisanje i in-silico predviđanje potencijalne biološke aktivnosti novosintetisanih derivata sukcinimida.",
publisher = "Belgrade : Association of the Chemical Engineers of Serbia",
journal = "Hemijska industrija",
title = "Spectroscopic and quantum chemical elucidation of newly synthesized 1-aryl-3-methyl-3-phenylpyrrolidine-2,5-diones as potential anticonvulsant agents",
volume = "73",
number = "2",
pages = "125-137",
doi = "10.2298/HEMIND190214011P"
}

Petković Cvetković, J., Božić, B., Banjac, N. R., Lađarević, J., Vitnik, V., Vitnik, Ž., Valentić, N. V.,& Ušćumlić, G.. (2019). Spectroscopic and quantum chemical elucidation of newly synthesized 1-aryl-3-methyl-3-phenylpyrrolidine-2,5-diones as potential anticonvulsant agents. in Hemijska industrija
Belgrade : Association of the Chemical Engineers of Serbia., 73(2), 125-137.
https://doi.org/10.2298/HEMIND190214011P

Petković Cvetković J, Božić B, Banjac NR, Lađarević J, Vitnik V, Vitnik Ž, Valentić NV, Ušćumlić G. Spectroscopic and quantum chemical elucidation of newly synthesized 1-aryl-3-methyl-3-phenylpyrrolidine-2,5-diones as potential anticonvulsant agents. in Hemijska industrija. 2019;73(2):125-137.
doi:10.2298/HEMIND190214011P .

Petković Cvetković, Jelena, Božić, Bojan, Banjac, Nebojša R., Lađarević, Jelena, Vitnik, Vesna, Vitnik, Željko, Valentić, Nataša V., Ušćumlić, Gordana, "Spectroscopic and quantum chemical elucidation of newly synthesized 1-aryl-3-methyl-3-phenylpyrrolidine-2,5-diones as potential anticonvulsant agents" in Hemijska industrija, 73, no. 2 (2019):125-137,
https://doi.org/10.2298/HEMIND190214011P . .

TY  - JOUR
AU  - Božić, Bojan
AU  - Lović, Jelena
AU  - Banjac, Nebojša R.
AU  - Vitnik, Željko
AU  - Vitnik, Vesna
AU  - Mijin, Dušan
AU  - Ušćumlić, Gordana
AU  - Avramov Ivić, Milka
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2300
AB  - A series of succinimide derivatives were studied using the cyclic and square wave voltammetry. Density function theory was used in order to determinate which of the structural parameters influence the electrochemical activity. The quantum chemical calculations of the investigated succinimides were linked with the experimental electrochemical data and used to propose the oxidation mechanism. The most active among studied succinimides is 1,3-diphenylsuccinimide. The results obtained from the cyclic and square wave voltammetry and quantum chemical calculations indicate that the investigated compounds undergo oxidation by irreversible, diffusion controlled process including transfer of 1e(-) and 1 proton. The voltammetric and DFT results signify that the mechanism of electrochemical oxidation of all compounds involve the conversion of carbonyl-methyne-phenyl segment or methylene group in free radical. This conversion proceeds by the loss of one proton one electron process.
PB  - Esg, Belgrade
T2  - International Journal of Electrochemical Science
T1  - Voltammetric and Quantum Investigation of Selected Succinimides
VL  - 13
IS  - 5
SP  - 4285
EP  - 4297
DO  - 10.20964/2018.05.54
ER  - 

@article{
author = "Božić, Bojan and Lović, Jelena and Banjac, Nebojša R. and Vitnik, Željko and Vitnik, Vesna and Mijin, Dušan and Ušćumlić, Gordana and Avramov Ivić, Milka",
year = "2018",
abstract = "A series of succinimide derivatives were studied using the cyclic and square wave voltammetry. Density function theory was used in order to determinate which of the structural parameters influence the electrochemical activity. The quantum chemical calculations of the investigated succinimides were linked with the experimental electrochemical data and used to propose the oxidation mechanism. The most active among studied succinimides is 1,3-diphenylsuccinimide. The results obtained from the cyclic and square wave voltammetry and quantum chemical calculations indicate that the investigated compounds undergo oxidation by irreversible, diffusion controlled process including transfer of 1e(-) and 1 proton. The voltammetric and DFT results signify that the mechanism of electrochemical oxidation of all compounds involve the conversion of carbonyl-methyne-phenyl segment or methylene group in free radical. This conversion proceeds by the loss of one proton one electron process.",
publisher = "Esg, Belgrade",
journal = "International Journal of Electrochemical Science",
title = "Voltammetric and Quantum Investigation of Selected Succinimides",
volume = "13",
number = "5",
pages = "4285-4297",
doi = "10.20964/2018.05.54"
}

Božić, B., Lović, J., Banjac, N. R., Vitnik, Ž., Vitnik, V., Mijin, D., Ušćumlić, G.,& Avramov Ivić, M.. (2018). Voltammetric and Quantum Investigation of Selected Succinimides. in International Journal of Electrochemical Science
Esg, Belgrade., 13(5), 4285-4297.
https://doi.org/10.20964/2018.05.54

Božić B, Lović J, Banjac NR, Vitnik Ž, Vitnik V, Mijin D, Ušćumlić G, Avramov Ivić M. Voltammetric and Quantum Investigation of Selected Succinimides. in International Journal of Electrochemical Science. 2018;13(5):4285-4297.
doi:10.20964/2018.05.54 .

Božić, Bojan, Lović, Jelena, Banjac, Nebojša R., Vitnik, Željko, Vitnik, Vesna, Mijin, Dušan, Ušćumlić, Gordana, Avramov Ivić, Milka, "Voltammetric and Quantum Investigation of Selected Succinimides" in International Journal of Electrochemical Science, 13, no. 5 (2018):4285-4297,
https://doi.org/10.20964/2018.05.54 . .

TY  - JOUR
AU  - Mirkovic, Jelena
AU  - Božić, Bojan
AU  - Vitnik, Vesna
AU  - Vitnik, Željko
AU  - Rogan, Jelena R.
AU  - Poleti, Dejan
AU  - Ušćumlić, Gordana
AU  - Mijin, Dušan
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2318
AB  - Ten 5-(substituted phenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridones were studied (five new compounds) to provide insight into the electronic effects of diverse substituents located at different positions in their phenyl moieties. The structural features of these dyes were examined by combining experimental and theoretical approaches. The crystal structures of two derivatives were revealed by X-ray crystallography and diverse packing modes owing to different intermolecular interactions (- stacking and lone pair- interactions, as well as hydrogen bonds) were found. A study on lattice energy and energy related to the molecular pairs obtained from their crystal packing was performed. The tautomerism and ionisation of the dyes in ethanol or N,N -dimethylformamide solution were rationalised in terms of diazo component substitution pattern.
PB  - Blackwell Publishing Ltd
T2  - Coloration Technology
T1  - Structural, spectroscopic and computational study of 5-(substituted phenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridones
VL  - 134
IS  - 1
SP  - 33
EP  - 43
DO  - 10.1111/cote.12321
ER  - 

@article{
author = "Mirkovic, Jelena and Božić, Bojan and Vitnik, Vesna and Vitnik, Željko and Rogan, Jelena R. and Poleti, Dejan and Ušćumlić, Gordana and Mijin, Dušan",
year = "2018",
abstract = "Ten 5-(substituted phenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridones were studied (five new compounds) to provide insight into the electronic effects of diverse substituents located at different positions in their phenyl moieties. The structural features of these dyes were examined by combining experimental and theoretical approaches. The crystal structures of two derivatives were revealed by X-ray crystallography and diverse packing modes owing to different intermolecular interactions (- stacking and lone pair- interactions, as well as hydrogen bonds) were found. A study on lattice energy and energy related to the molecular pairs obtained from their crystal packing was performed. The tautomerism and ionisation of the dyes in ethanol or N,N -dimethylformamide solution were rationalised in terms of diazo component substitution pattern.",
publisher = "Blackwell Publishing Ltd",
journal = "Coloration Technology",
title = "Structural, spectroscopic and computational study of 5-(substituted phenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridones",
volume = "134",
number = "1",
pages = "33-43",
doi = "10.1111/cote.12321"
}

Mirkovic, J., Božić, B., Vitnik, V., Vitnik, Ž., Rogan, J. R., Poleti, D., Ušćumlić, G.,& Mijin, D.. (2018). Structural, spectroscopic and computational study of 5-(substituted phenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridones. in Coloration Technology
Blackwell Publishing Ltd., 134(1), 33-43.
https://doi.org/10.1111/cote.12321

Mirkovic J, Božić B, Vitnik V, Vitnik Ž, Rogan JR, Poleti D, Ušćumlić G, Mijin D. Structural, spectroscopic and computational study of 5-(substituted phenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridones. in Coloration Technology. 2018;134(1):33-43.
doi:10.1111/cote.12321 .

Mirkovic, Jelena, Božić, Bojan, Vitnik, Vesna, Vitnik, Željko, Rogan, Jelena R., Poleti, Dejan, Ušćumlić, Gordana, Mijin, Dušan, "Structural, spectroscopic and computational study of 5-(substituted phenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridones" in Coloration Technology, 134, no. 1 (2018):33-43,
https://doi.org/10.1111/cote.12321 . .

TY  - JOUR
AU  - Mijin, Dušan
AU  - Božić, Bojan
AU  - Lađarević, Jelena
AU  - Matović, Luka
AU  - Ušćumlić, Gordana
AU  - Vitnik, Vesna
AU  - Vitnik, Željko
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2412
AB  - Disazo pyridone dye, 4-methyl-2,6-dioxo-5-(2-(4-(phenyldiazenyl)phenyl)hydrazono)-1,2,5,6-tetrahydropyridine-3-carbonitrile, is synthesised and thoroughly characterised by a combination of experimental and computational approaches. Fourier Transform-infrared and nuclear magnetic resonance (NMR) spectra prove the existence of the hydrazone form in the solid state and in dimethyl sulphoxide, which is also supported by vibrational and NMR theoretical studies. Ultraviolet (UV) spectral properties, as well as solvatochromism in 19 solvents of different polarity, are investigated. In most of the solvents, the dye is solely present in the hydrazone form, whereas in certain solvents, an acid–base equilibrium exists. Excellent agreement between computational and experimental UV–visible data was established. Frontier Molecular Orbital analysis was performed and proved the existence of intramolecular charge transfer through the dye molecule. A molecular electrostatic potential surface was plotted over the optimised geometry to lighten the reactivity of the investigated molecule.
PB  - Blackwell Publishing Ltd
T2  - Coloration Technology
T1  - Solvatochromism and quantum mechanical investigation of disazo pyridone dye
VL  - 134
IS  - 6
SP  - 478
EP  - 490
DO  - 10.1111/cote.12369
ER  - 

@article{
author = "Mijin, Dušan and Božić, Bojan and Lađarević, Jelena and Matović, Luka and Ušćumlić, Gordana and Vitnik, Vesna and Vitnik, Željko",
year = "2018",
abstract = "Disazo pyridone dye, 4-methyl-2,6-dioxo-5-(2-(4-(phenyldiazenyl)phenyl)hydrazono)-1,2,5,6-tetrahydropyridine-3-carbonitrile, is synthesised and thoroughly characterised by a combination of experimental and computational approaches. Fourier Transform-infrared and nuclear magnetic resonance (NMR) spectra prove the existence of the hydrazone form in the solid state and in dimethyl sulphoxide, which is also supported by vibrational and NMR theoretical studies. Ultraviolet (UV) spectral properties, as well as solvatochromism in 19 solvents of different polarity, are investigated. In most of the solvents, the dye is solely present in the hydrazone form, whereas in certain solvents, an acid–base equilibrium exists. Excellent agreement between computational and experimental UV–visible data was established. Frontier Molecular Orbital analysis was performed and proved the existence of intramolecular charge transfer through the dye molecule. A molecular electrostatic potential surface was plotted over the optimised geometry to lighten the reactivity of the investigated molecule.",
publisher = "Blackwell Publishing Ltd",
journal = "Coloration Technology",
title = "Solvatochromism and quantum mechanical investigation of disazo pyridone dye",
volume = "134",
number = "6",
pages = "478-490",
doi = "10.1111/cote.12369"
}

Mijin, D., Božić, B., Lađarević, J., Matović, L., Ušćumlić, G., Vitnik, V.,& Vitnik, Ž.. (2018). Solvatochromism and quantum mechanical investigation of disazo pyridone dye. in Coloration Technology
Blackwell Publishing Ltd., 134(6), 478-490.
https://doi.org/10.1111/cote.12369

Mijin D, Božić B, Lađarević J, Matović L, Ušćumlić G, Vitnik V, Vitnik Ž. Solvatochromism and quantum mechanical investigation of disazo pyridone dye. in Coloration Technology. 2018;134(6):478-490.
doi:10.1111/cote.12369 .

Mijin, Dušan, Božić, Bojan, Lađarević, Jelena, Matović, Luka, Ušćumlić, Gordana, Vitnik, Vesna, Vitnik, Željko, "Solvatochromism and quantum mechanical investigation of disazo pyridone dye" in Coloration Technology, 134, no. 6 (2018):478-490,
https://doi.org/10.1111/cote.12369 . .

TY  - JOUR
AU  - Vitnik, Vesna
AU  - Vitnik, Željko
AU  - Božić, Bojan
AU  - Valentić, Nataša V.
AU  - Dilber, Sanda P.
AU  - Mijin, Dušan
AU  - Ušćumlić, Gordana
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2262
AB  - In this paper, spectroscopic and quantum mechanical investigation of nine 4-aryl-5-arylazo-3-cyano-6-hydroxy-2-pyridone dyes was performed, and obtained density functional theory (DFT) results were compared with experimental data. The structural and spectroscopic properties of azo-2-pyridone dyes were studied by DFT using B3LYP, CAM-B3LYP, and M06-2X methods with a 6-311++G(d,p) basis set. Comparison of results reveals that the scaled theoretical vibrational frequencies of azo dyes are in good agreement with experimental data. The time-dependent DFT calculated and experimental ultraviolet-visible (UV-vis) absorption spectra are also in good agreement. The effect of electron-donating -OCH3 and electron-withdrawing -NO2 groups on the structural parameters, vibrational frequencies, UV-vis absorption, and natural bond orbital (NBO) atomic charges were thoroughly analysed. Vibrational, UV-vis, and NBO analyses confirm that investigated dyes exist in the hydrazo tautomeric form in the solid state and ethanol solution. These analyses signify the occurrence of intramolecular charge transfer in these azo-pyridone dyes.
PB  - Blackwell Publishing Ltd
T2  - Coloration Technology
T1  - Experimental and theoretical insight into the electronic properties of 4-aryl-5-arylazo-3-cyano-6-hydroxy-2-pyridone dyes
VL  - 133
IS  - 3
SP  - 223
EP  - 233
DO  - 10.1111/cote.12271
ER  - 

@article{
author = "Vitnik, Vesna and Vitnik, Željko and Božić, Bojan and Valentić, Nataša V. and Dilber, Sanda P. and Mijin, Dušan and Ušćumlić, Gordana",
year = "2017",
abstract = "In this paper, spectroscopic and quantum mechanical investigation of nine 4-aryl-5-arylazo-3-cyano-6-hydroxy-2-pyridone dyes was performed, and obtained density functional theory (DFT) results were compared with experimental data. The structural and spectroscopic properties of azo-2-pyridone dyes were studied by DFT using B3LYP, CAM-B3LYP, and M06-2X methods with a 6-311++G(d,p) basis set. Comparison of results reveals that the scaled theoretical vibrational frequencies of azo dyes are in good agreement with experimental data. The time-dependent DFT calculated and experimental ultraviolet-visible (UV-vis) absorption spectra are also in good agreement. The effect of electron-donating -OCH3 and electron-withdrawing -NO2 groups on the structural parameters, vibrational frequencies, UV-vis absorption, and natural bond orbital (NBO) atomic charges were thoroughly analysed. Vibrational, UV-vis, and NBO analyses confirm that investigated dyes exist in the hydrazo tautomeric form in the solid state and ethanol solution. These analyses signify the occurrence of intramolecular charge transfer in these azo-pyridone dyes.",
publisher = "Blackwell Publishing Ltd",
journal = "Coloration Technology",
title = "Experimental and theoretical insight into the electronic properties of 4-aryl-5-arylazo-3-cyano-6-hydroxy-2-pyridone dyes",
volume = "133",
number = "3",
pages = "223-233",
doi = "10.1111/cote.12271"
}

Vitnik, V., Vitnik, Ž., Božić, B., Valentić, N. V., Dilber, S. P., Mijin, D.,& Ušćumlić, G.. (2017). Experimental and theoretical insight into the electronic properties of 4-aryl-5-arylazo-3-cyano-6-hydroxy-2-pyridone dyes. in Coloration Technology
Blackwell Publishing Ltd., 133(3), 223-233.
https://doi.org/10.1111/cote.12271

Vitnik V, Vitnik Ž, Božić B, Valentić NV, Dilber SP, Mijin D, Ušćumlić G. Experimental and theoretical insight into the electronic properties of 4-aryl-5-arylazo-3-cyano-6-hydroxy-2-pyridone dyes. in Coloration Technology. 2017;133(3):223-233.
doi:10.1111/cote.12271 .

Vitnik, Vesna, Vitnik, Željko, Božić, Bojan, Valentić, Nataša V., Dilber, Sanda P., Mijin, Dušan, Ušćumlić, Gordana, "Experimental and theoretical insight into the electronic properties of 4-aryl-5-arylazo-3-cyano-6-hydroxy-2-pyridone dyes" in Coloration Technology, 133, no. 3 (2017):223-233,
https://doi.org/10.1111/cote.12271 . .

TY  - JOUR
AU  - Banjac, Nebojša R.
AU  - Božić, Bojan
AU  - Mirkovic, Jelena M.
AU  - Vitnik, Vesna
AU  - Vitnik, Željko
AU  - Valentić, Nataša V.
AU  - Ušćumlić, Gordana
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2054
AB  - A series of ten 1-aryl-3-methylsuccinimides was synthesized and their solvatochromic properties were studied in a set of fifteen binary solvent mixtures. The solute-solvent interactions were analyzed on the basis of the linear solvation energy relationship (LSER) concept proposed by Kamlet and Taft. The electronic effect of the substituents on the UV-Vis absorption and NMR spectra was analyzed using the simple Hammett equation. Moreover, the B3LYP, CAM-B3LYP, and M06-2X functionals using the 6-311G(d,p) basic set have been assessed in light of the position of experimental absorption maxima obtained for these compounds. The integration grid effects have also been evaluated. An interpretation of the substituent-effect transmission through the molecular skeleton and the nature of the HOMO and LUMO orbitals based on quantum-chemical calculations is given. The values of partial atomic charges from the atomic polar tenzors (APT), natural population analysis (NBO), and charges fit to the electrostatic potential using the B3LYP, CAM-B3LYP, and M06-2X methods are produced and correlated with different experimental properties. In order to estimate the chemical activity of the molecule, the molecular electrostatic potential (MEP) surface map is calculated for the optimized geometry of 1-phenyl-3-methylsuccinimide.
PB  - Elsevier
T2  - Journal of Molecular Structure
T1  - Experimental and theoretical study on the structure-property relationship of novel 1-aryl-3-methylsuccinimides
VL  - 1129
SP  - 271
EP  - 282
DO  - 10.1016/j.molstruc.2016.09.086
ER  - 

@article{
author = "Banjac, Nebojša R. and Božić, Bojan and Mirkovic, Jelena M. and Vitnik, Vesna and Vitnik, Željko and Valentić, Nataša V. and Ušćumlić, Gordana",
year = "2017",
abstract = "A series of ten 1-aryl-3-methylsuccinimides was synthesized and their solvatochromic properties were studied in a set of fifteen binary solvent mixtures. The solute-solvent interactions were analyzed on the basis of the linear solvation energy relationship (LSER) concept proposed by Kamlet and Taft. The electronic effect of the substituents on the UV-Vis absorption and NMR spectra was analyzed using the simple Hammett equation. Moreover, the B3LYP, CAM-B3LYP, and M06-2X functionals using the 6-311G(d,p) basic set have been assessed in light of the position of experimental absorption maxima obtained for these compounds. The integration grid effects have also been evaluated. An interpretation of the substituent-effect transmission through the molecular skeleton and the nature of the HOMO and LUMO orbitals based on quantum-chemical calculations is given. The values of partial atomic charges from the atomic polar tenzors (APT), natural population analysis (NBO), and charges fit to the electrostatic potential using the B3LYP, CAM-B3LYP, and M06-2X methods are produced and correlated with different experimental properties. In order to estimate the chemical activity of the molecule, the molecular electrostatic potential (MEP) surface map is calculated for the optimized geometry of 1-phenyl-3-methylsuccinimide.",
publisher = "Elsevier",
journal = "Journal of Molecular Structure",
title = "Experimental and theoretical study on the structure-property relationship of novel 1-aryl-3-methylsuccinimides",
volume = "1129",
pages = "271-282",
doi = "10.1016/j.molstruc.2016.09.086"
}

Banjac, N. R., Božić, B., Mirkovic, J. M., Vitnik, V., Vitnik, Ž., Valentić, N. V.,& Ušćumlić, G.. (2017). Experimental and theoretical study on the structure-property relationship of novel 1-aryl-3-methylsuccinimides. in Journal of Molecular Structure
Elsevier., 1129, 271-282.
https://doi.org/10.1016/j.molstruc.2016.09.086

Banjac NR, Božić B, Mirkovic JM, Vitnik V, Vitnik Ž, Valentić NV, Ušćumlić G. Experimental and theoretical study on the structure-property relationship of novel 1-aryl-3-methylsuccinimides. in Journal of Molecular Structure. 2017;1129:271-282.
doi:10.1016/j.molstruc.2016.09.086 .

Banjac, Nebojša R., Božić, Bojan, Mirkovic, Jelena M., Vitnik, Vesna, Vitnik, Željko, Valentić, Nataša V., Ušćumlić, Gordana, "Experimental and theoretical study on the structure-property relationship of novel 1-aryl-3-methylsuccinimides" in Journal of Molecular Structure, 1129 (2017):271-282,
https://doi.org/10.1016/j.molstruc.2016.09.086 . .

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 . .

TY  - JOUR
AU  - Banjac, Nebojša R.
AU  - Božić, Bojan
AU  - Mirkovic, Jelena M.
AU  - Vitnik, Vesna
AU  - Vitnik, Željko
AU  - Valentić, Nataša V.
AU  - Ušćumlić, Gordana
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3029
AB  - A series of ten 1-aryl-3-methylsuccinimides was synthesized and their solvatochromic properties were studied in a set of fifteen binary solvent mixtures. The solute-solvent interactions were analyzed on the basis of the linear solvation energy relationship (LSER) concept proposed by Kamlet and Taft. The electronic effect of the substituents on the UV-Vis absorption and NMR spectra was analyzed using the simple Hammett equation. Moreover, the B3LYP, CAM-B3LYP, and M06-2X functionals using the 6-311G(d,p) basic set have been assessed in light of the position of experimental absorption maxima obtained for these compounds. The integration grid effects have also been evaluated. An interpretation of the substituent-effect transmission through the molecular skeleton and the nature of the HOMO and LUMO orbitals based on quantum-chemical calculations is given. The values of partial atomic charges from the atomic polar tenzors (APT), natural population analysis (NBO), and charges fit to the electrostatic potential using the B3LYP, CAM-B3LYP, and M06-2X methods are produced and correlated with different experimental properties. In order to estimate the chemical activity of the molecule, the molecular electrostatic potential (MEP) surface map is calculated for the optimized geometry of 1-phenyl-3-methylsuccinimide.
PB  - Elsevier
T2  - Journal of Molecular Structure
T1  - Experimental and theoretical study on the structure-property relationship of novel 1-aryl-3-methylsuccinimides
VL  - 1129
SP  - 271
EP  - 282
DO  - 10.1016/j.molstruc.2016.09.086
ER  - 

@article{
author = "Banjac, Nebojša R. and Božić, Bojan and Mirkovic, Jelena M. and Vitnik, Vesna and Vitnik, Željko and Valentić, Nataša V. and Ušćumlić, Gordana",
year = "2017",
abstract = "A series of ten 1-aryl-3-methylsuccinimides was synthesized and their solvatochromic properties were studied in a set of fifteen binary solvent mixtures. The solute-solvent interactions were analyzed on the basis of the linear solvation energy relationship (LSER) concept proposed by Kamlet and Taft. The electronic effect of the substituents on the UV-Vis absorption and NMR spectra was analyzed using the simple Hammett equation. Moreover, the B3LYP, CAM-B3LYP, and M06-2X functionals using the 6-311G(d,p) basic set have been assessed in light of the position of experimental absorption maxima obtained for these compounds. The integration grid effects have also been evaluated. An interpretation of the substituent-effect transmission through the molecular skeleton and the nature of the HOMO and LUMO orbitals based on quantum-chemical calculations is given. The values of partial atomic charges from the atomic polar tenzors (APT), natural population analysis (NBO), and charges fit to the electrostatic potential using the B3LYP, CAM-B3LYP, and M06-2X methods are produced and correlated with different experimental properties. In order to estimate the chemical activity of the molecule, the molecular electrostatic potential (MEP) surface map is calculated for the optimized geometry of 1-phenyl-3-methylsuccinimide.",
publisher = "Elsevier",
journal = "Journal of Molecular Structure",
title = "Experimental and theoretical study on the structure-property relationship of novel 1-aryl-3-methylsuccinimides",
volume = "1129",
pages = "271-282",
doi = "10.1016/j.molstruc.2016.09.086"
}

Banjac, N. R., Božić, B., Mirkovic, J. M., Vitnik, V., Vitnik, Ž., Valentić, N. V.,& Ušćumlić, G.. (2017). Experimental and theoretical study on the structure-property relationship of novel 1-aryl-3-methylsuccinimides. in Journal of Molecular Structure
Elsevier., 1129, 271-282.
https://doi.org/10.1016/j.molstruc.2016.09.086

Banjac NR, Božić B, Mirkovic JM, Vitnik V, Vitnik Ž, Valentić NV, Ušćumlić G. Experimental and theoretical study on the structure-property relationship of novel 1-aryl-3-methylsuccinimides. in Journal of Molecular Structure. 2017;1129:271-282.
doi:10.1016/j.molstruc.2016.09.086 .

Banjac, Nebojša R., Božić, Bojan, Mirkovic, Jelena M., Vitnik, Vesna, Vitnik, Željko, Valentić, Nataša V., Ušćumlić, Gordana, "Experimental and theoretical study on the structure-property relationship of novel 1-aryl-3-methylsuccinimides" in Journal of Molecular Structure, 1129 (2017):271-282,
https://doi.org/10.1016/j.molstruc.2016.09.086 . .

TY  - JOUR
AU  - Arsovski, Violeta M
AU  - Božić, Bojan
AU  - Mirkovic, Jelena M
AU  - Vitnik, Vesna
AU  - Vitnik, Željko
AU  - Petrović, Slobodan D.
AU  - Ušćumlić, Gordana
AU  - Mijin, Dušan
PY  - 2015
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1719
AB  - To complement a previous UV study, we present a quantitative evaluation of substituent effects on spectroscopic data (H-1 and C-13 NMR chemical shifts as well as FT-IR absorption frequency) applied to N, N'-bisarylmalonamides, using simple and extended Hammett equations as well as the Swain-Lupton equation. Furthermore, the DFT CAM-B3LYP/6-311+G(d,p) method was applied to study the impact of different solvents on the geometry of the molecules and their spectral data. Additionally, experimental data are correlated with theoretical results; excellent linear dependence was obtained. The overall results presented in this paper show that N, N'-bisarylmalonamides are prominent candidates for model molecules.
PB  - Springer, New York
T2  - Journal of Molecular Modeling
T1  - Computational and spectroscopic data correlation study of N,N '-bisarylmalonamides (Part II)
VL  - 21
IS  - 9
DO  - 10.1007/s00894-015-2777-z
ER  - 

@article{
author = "Arsovski, Violeta M and Božić, Bojan and Mirkovic, Jelena M and Vitnik, Vesna and Vitnik, Željko and Petrović, Slobodan D. and Ušćumlić, Gordana and Mijin, Dušan",
year = "2015",
abstract = "To complement a previous UV study, we present a quantitative evaluation of substituent effects on spectroscopic data (H-1 and C-13 NMR chemical shifts as well as FT-IR absorption frequency) applied to N, N'-bisarylmalonamides, using simple and extended Hammett equations as well as the Swain-Lupton equation. Furthermore, the DFT CAM-B3LYP/6-311+G(d,p) method was applied to study the impact of different solvents on the geometry of the molecules and their spectral data. Additionally, experimental data are correlated with theoretical results; excellent linear dependence was obtained. The overall results presented in this paper show that N, N'-bisarylmalonamides are prominent candidates for model molecules.",
publisher = "Springer, New York",
journal = "Journal of Molecular Modeling",
title = "Computational and spectroscopic data correlation study of N,N '-bisarylmalonamides (Part II)",
volume = "21",
number = "9",
doi = "10.1007/s00894-015-2777-z"
}

Arsovski, V. M., Božić, B., Mirkovic, J. M., Vitnik, V., Vitnik, Ž., Petrović, S. D., Ušćumlić, G.,& Mijin, D.. (2015). Computational and spectroscopic data correlation study of N,N '-bisarylmalonamides (Part II). in Journal of Molecular Modeling
Springer, New York., 21(9).
https://doi.org/10.1007/s00894-015-2777-z

Arsovski VM, Božić B, Mirkovic JM, Vitnik V, Vitnik Ž, Petrović SD, Ušćumlić G, Mijin D. Computational and spectroscopic data correlation study of N,N '-bisarylmalonamides (Part II). in Journal of Molecular Modeling. 2015;21(9).
doi:10.1007/s00894-015-2777-z .

Arsovski, Violeta M, Božić, Bojan, Mirkovic, Jelena M, Vitnik, Vesna, Vitnik, Željko, Petrović, Slobodan D., Ušćumlić, Gordana, Mijin, Dušan, "Computational and spectroscopic data correlation study of N,N '-bisarylmalonamides (Part II)" in Journal of Molecular Modeling, 21, no. 9 (2015),
https://doi.org/10.1007/s00894-015-2777-z . .

TY  - JOUR
AU  - Vitnik, Vesna
AU  - Vitnik, Željko
AU  - Banjac, Nebojša R.
AU  - Valentić, Nataša V.
AU  - Ušćumlić, Gordana
AU  - Juranić, Ivan
PY  - 2014
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3160
AB  - This study represents an integrated approach towards understanding the vibrational, electronic, NMR, and structural aspects, and reactivity of 1-(4-chloro-phenyl)-3-phenyl-succinimide (CPPS). A detailed interpretation of the FT-IR, UV and NMR spectra were reported. The equilibrium geometry, bonding features, and harmonic vibrational frequencies have been investigated with the help of density functional theory (DFT) B3LYP method using 6-31G(d,p) and 6-311++G(d,p) basis set. The scaled theoretical wave-number showed very good agreement with the experimental values. The H-1 and C-13 nuclear magnetic resonance (NMR) chemical shifts of the molecule were calculated by the Gauge-Invariant Atomic Orbital (GIAO) method. Stability of the molecule, arising from hyperconjugative interactions and charge delocalization, has been analyzed using Natural Bond Orbital (NBO) analysis. The results show that ED in the sigma* and pi* antibonding orbitals and second order delocalization energies E(2) confirm the occurrence of intramolecular charge transfer (ICT) within the molecule. UV-Vis spectrum of the compound was recorded and the electronic properties, such as HOMO and LUMO energies, were calculated by Time-Dependent (TD-DFT) approach. To estimate chemical reactivity of the molecule, the molecular electrostatic potential (MEP) surface map is calculated for the optimized geometry of the molecule.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy
T1  - Quantum mechanical and spectroscopic (FT-IR, C-13, H-1 NMR and UV) investigations of potent antiepileptic drug 1-(4-chloro-phenyl)-3-phenyl-succinimide
VL  - 117
SP  - 42
EP  - 53
DO  - 10.1016/j.saa.2013.07.099
ER  - 

@article{
author = "Vitnik, Vesna and Vitnik, Željko and Banjac, Nebojša R. and Valentić, Nataša V. and Ušćumlić, Gordana and Juranić, Ivan",
year = "2014",
abstract = "This study represents an integrated approach towards understanding the vibrational, electronic, NMR, and structural aspects, and reactivity of 1-(4-chloro-phenyl)-3-phenyl-succinimide (CPPS). A detailed interpretation of the FT-IR, UV and NMR spectra were reported. The equilibrium geometry, bonding features, and harmonic vibrational frequencies have been investigated with the help of density functional theory (DFT) B3LYP method using 6-31G(d,p) and 6-311++G(d,p) basis set. The scaled theoretical wave-number showed very good agreement with the experimental values. The H-1 and C-13 nuclear magnetic resonance (NMR) chemical shifts of the molecule were calculated by the Gauge-Invariant Atomic Orbital (GIAO) method. Stability of the molecule, arising from hyperconjugative interactions and charge delocalization, has been analyzed using Natural Bond Orbital (NBO) analysis. The results show that ED in the sigma* and pi* antibonding orbitals and second order delocalization energies E(2) confirm the occurrence of intramolecular charge transfer (ICT) within the molecule. UV-Vis spectrum of the compound was recorded and the electronic properties, such as HOMO and LUMO energies, were calculated by Time-Dependent (TD-DFT) approach. To estimate chemical reactivity of the molecule, the molecular electrostatic potential (MEP) surface map is calculated for the optimized geometry of the molecule.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy",
title = "Quantum mechanical and spectroscopic (FT-IR, C-13, H-1 NMR and UV) investigations of potent antiepileptic drug 1-(4-chloro-phenyl)-3-phenyl-succinimide",
volume = "117",
pages = "42-53",
doi = "10.1016/j.saa.2013.07.099"
}

Vitnik, V., Vitnik, Ž., Banjac, N. R., Valentić, N. V., Ušćumlić, G.,& Juranić, I.. (2014). Quantum mechanical and spectroscopic (FT-IR, C-13, H-1 NMR and UV) investigations of potent antiepileptic drug 1-(4-chloro-phenyl)-3-phenyl-succinimide. in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy
Oxford : Pergamon-Elsevier Science Ltd., 117, 42-53.
https://doi.org/10.1016/j.saa.2013.07.099

Vitnik V, Vitnik Ž, Banjac NR, Valentić NV, Ušćumlić G, Juranić I. Quantum mechanical and spectroscopic (FT-IR, C-13, H-1 NMR and UV) investigations of potent antiepileptic drug 1-(4-chloro-phenyl)-3-phenyl-succinimide. in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy. 2014;117:42-53.
doi:10.1016/j.saa.2013.07.099 .

Vitnik, Vesna, Vitnik, Željko, Banjac, Nebojša R., Valentić, Nataša V., Ušćumlić, Gordana, Juranić, Ivan, "Quantum mechanical and spectroscopic (FT-IR, C-13, H-1 NMR and UV) investigations of potent antiepileptic drug 1-(4-chloro-phenyl)-3-phenyl-succinimide" in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy, 117 (2014):42-53,
https://doi.org/10.1016/j.saa.2013.07.099 . .

TY  - JOUR
AU  - Vitnik, Vesna
AU  - Vitnik, Željko
AU  - Banjac, Nebojša R.
AU  - Valentić, Nataša V.
AU  - Ušćumlić, Gordana
AU  - Juranić, Ivan
PY  - 2014
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1496
AB  - This study represents an integrated approach towards understanding the vibrational, electronic, NMR, and structural aspects, and reactivity of 1-(4-chloro-phenyl)-3-phenyl-succinimide (CPPS). A detailed interpretation of the FT-IR, UV and NMR spectra were reported. The equilibrium geometry, bonding features, and harmonic vibrational frequencies have been investigated with the help of density functional theory (DFT) B3LYP method using 6-31G(d,p) and 6-311++G(d,p) basis set. The scaled theoretical wave-number showed very good agreement with the experimental values. The H-1 and C-13 nuclear magnetic resonance (NMR) chemical shifts of the molecule were calculated by the Gauge-Invariant Atomic Orbital (GIAO) method. Stability of the molecule, arising from hyperconjugative interactions and charge delocalization, has been analyzed using Natural Bond Orbital (NBO) analysis. The results show that ED in the sigma* and pi* antibonding orbitals and second order delocalization energies E(2) confirm the occurrence of intramolecular charge transfer (ICT) within the molecule. UV-Vis spectrum of the compound was recorded and the electronic properties, such as HOMO and LUMO energies, were calculated by Time-Dependent (TD-DFT) approach. To estimate chemical reactivity of the molecule, the molecular electrostatic potential (MEP) surface map is calculated for the optimized geometry of the molecule.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy
T1  - Quantum mechanical and spectroscopic (FT-IR, C-13, H-1 NMR and UV) investigations of potent antiepileptic drug 1-(4-chloro-phenyl)-3-phenyl-succinimide
VL  - 117
SP  - 42
EP  - 53
DO  - 10.1016/j.saa.2013.07.099
ER  - 

@article{
author = "Vitnik, Vesna and Vitnik, Željko and Banjac, Nebojša R. and Valentić, Nataša V. and Ušćumlić, Gordana and Juranić, Ivan",
year = "2014",
abstract = "This study represents an integrated approach towards understanding the vibrational, electronic, NMR, and structural aspects, and reactivity of 1-(4-chloro-phenyl)-3-phenyl-succinimide (CPPS). A detailed interpretation of the FT-IR, UV and NMR spectra were reported. The equilibrium geometry, bonding features, and harmonic vibrational frequencies have been investigated with the help of density functional theory (DFT) B3LYP method using 6-31G(d,p) and 6-311++G(d,p) basis set. The scaled theoretical wave-number showed very good agreement with the experimental values. The H-1 and C-13 nuclear magnetic resonance (NMR) chemical shifts of the molecule were calculated by the Gauge-Invariant Atomic Orbital (GIAO) method. Stability of the molecule, arising from hyperconjugative interactions and charge delocalization, has been analyzed using Natural Bond Orbital (NBO) analysis. The results show that ED in the sigma* and pi* antibonding orbitals and second order delocalization energies E(2) confirm the occurrence of intramolecular charge transfer (ICT) within the molecule. UV-Vis spectrum of the compound was recorded and the electronic properties, such as HOMO and LUMO energies, were calculated by Time-Dependent (TD-DFT) approach. To estimate chemical reactivity of the molecule, the molecular electrostatic potential (MEP) surface map is calculated for the optimized geometry of the molecule.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy",
title = "Quantum mechanical and spectroscopic (FT-IR, C-13, H-1 NMR and UV) investigations of potent antiepileptic drug 1-(4-chloro-phenyl)-3-phenyl-succinimide",
volume = "117",
pages = "42-53",
doi = "10.1016/j.saa.2013.07.099"
}

Vitnik, V., Vitnik, Ž., Banjac, N. R., Valentić, N. V., Ušćumlić, G.,& Juranić, I.. (2014). Quantum mechanical and spectroscopic (FT-IR, C-13, H-1 NMR and UV) investigations of potent antiepileptic drug 1-(4-chloro-phenyl)-3-phenyl-succinimide. in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy
Oxford : Pergamon-Elsevier Science Ltd., 117, 42-53.
https://doi.org/10.1016/j.saa.2013.07.099

Vitnik V, Vitnik Ž, Banjac NR, Valentić NV, Ušćumlić G, Juranić I. Quantum mechanical and spectroscopic (FT-IR, C-13, H-1 NMR and UV) investigations of potent antiepileptic drug 1-(4-chloro-phenyl)-3-phenyl-succinimide. in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy. 2014;117:42-53.
doi:10.1016/j.saa.2013.07.099 .

Vitnik, Vesna, Vitnik, Željko, Banjac, Nebojša R., Valentić, Nataša V., Ušćumlić, Gordana, Juranić, Ivan, "Quantum mechanical and spectroscopic (FT-IR, C-13, H-1 NMR and UV) investigations of potent antiepileptic drug 1-(4-chloro-phenyl)-3-phenyl-succinimide" in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy, 117 (2014):42-53,
https://doi.org/10.1016/j.saa.2013.07.099 . .

TY  - JOUR
AU  - Mirkovic, Jelena
AU  - Rogan, Jelena R.
AU  - Poleti, Dejan
AU  - Vitnik, Vesna
AU  - Vitnik, Željko
AU  - Ušćumlić, Gordana
AU  - Mijin, Dušan
PY  - 2014
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1509
AB  - In this work, a combined experimental and theoretical study on the structures of methoxy substituted 5-phenylazo-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridones has been reported. The dyes under the investigation have been thoroughly characterized. X-ray single-crystal analysis shows that 5-(4-methoxyphenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone crystallizes in the hydrazone form. Quantum chemical calculations of energies, geometrical structure and vibrational wavenumbers of the investigated dyes have been performed using density functional theory. The optimized geometrical parameters obtained by density functional theory calculations are in good conformity with the single-crystal data. The fundamental vibrational wavenumbers, as well as their intensities have been calculated and a good agreement between observed and scaled calculated wavenumbers has been achieved. Stability of the molecule arising from hyperconjugative interactions and charge delocalization has been analyzed using natural bond orbital analysis. Vibrational, nuclear magnetic resonance and natural bond orbital analysis confirm that the prepared dyes exist in the hydrazone tautomeric form in the solid state and dimethyl sulfoxide solution.
PB  - Elsevier Sci Ltd, Oxford
T2  - Dyes and Pigments
T1  - On the structures of 5-(4-, 3-and 2-methoxyphenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone: An experimental and theoretical study
VL  - 104
SP  - 160
EP  - 168
DO  - 10.1016/j.dyepig.2014.01.007
ER  - 

@article{
author = "Mirkovic, Jelena and Rogan, Jelena R. and Poleti, Dejan and Vitnik, Vesna and Vitnik, Željko and Ušćumlić, Gordana and Mijin, Dušan",
year = "2014",
abstract = "In this work, a combined experimental and theoretical study on the structures of methoxy substituted 5-phenylazo-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridones has been reported. The dyes under the investigation have been thoroughly characterized. X-ray single-crystal analysis shows that 5-(4-methoxyphenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone crystallizes in the hydrazone form. Quantum chemical calculations of energies, geometrical structure and vibrational wavenumbers of the investigated dyes have been performed using density functional theory. The optimized geometrical parameters obtained by density functional theory calculations are in good conformity with the single-crystal data. The fundamental vibrational wavenumbers, as well as their intensities have been calculated and a good agreement between observed and scaled calculated wavenumbers has been achieved. Stability of the molecule arising from hyperconjugative interactions and charge delocalization has been analyzed using natural bond orbital analysis. Vibrational, nuclear magnetic resonance and natural bond orbital analysis confirm that the prepared dyes exist in the hydrazone tautomeric form in the solid state and dimethyl sulfoxide solution.",
publisher = "Elsevier Sci Ltd, Oxford",
journal = "Dyes and Pigments",
title = "On the structures of 5-(4-, 3-and 2-methoxyphenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone: An experimental and theoretical study",
volume = "104",
pages = "160-168",
doi = "10.1016/j.dyepig.2014.01.007"
}

Mirkovic, J., Rogan, J. R., Poleti, D., Vitnik, V., Vitnik, Ž., Ušćumlić, G.,& Mijin, D.. (2014). On the structures of 5-(4-, 3-and 2-methoxyphenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone: An experimental and theoretical study. in Dyes and Pigments
Elsevier Sci Ltd, Oxford., 104, 160-168.
https://doi.org/10.1016/j.dyepig.2014.01.007

Mirkovic J, Rogan JR, Poleti D, Vitnik V, Vitnik Ž, Ušćumlić G, Mijin D. On the structures of 5-(4-, 3-and 2-methoxyphenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone: An experimental and theoretical study. in Dyes and Pigments. 2014;104:160-168.
doi:10.1016/j.dyepig.2014.01.007 .

Mirkovic, Jelena, Rogan, Jelena R., Poleti, Dejan, Vitnik, Vesna, Vitnik, Željko, Ušćumlić, Gordana, Mijin, Dušan, "On the structures of 5-(4-, 3-and 2-methoxyphenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone: An experimental and theoretical study" in Dyes and Pigments, 104 (2014):160-168,
https://doi.org/10.1016/j.dyepig.2014.01.007 . .

TY  - JOUR
AU  - Hmuda, Sleem
AU  - Trišović, Nemanja
AU  - Rogan, Jelena R.
AU  - Poleti, Dejan
AU  - Vitnik, Željko
AU  - Vitnik, Vesna
AU  - Valentić, Nataša V.
AU  - Bozic, Biljana
AU  - Ušćumlić, Gordana
PY  - 2014
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1518
AB  - Two new series of hydantoin derivatives, 3-(4-substituted benzyl)-5,5-diphenyl- and 3-(4-substituted benzyl)-5-ethyl-5-phenylhydantoins, were synthesized and their antiproliferative activity was tested against human colon cancer HCT-116 and breast cancer MDA-MB-231 cell lines. The presence of different substituents on both hydantoin and benzyl moieties changed the antiproliferative activity of the investigated hydantoins, whereby most of the compounds showed superior antiproliferative activity against MDA-MB-231 than against the HCT-116 cell line. The structure of three compounds was studied by single-crystal X-ray diffraction. The general structural characteristic is the presence of N-H center dot center dot center dot O hydrogen bonds in crystal packings. The molecular geometry and bonding features of the investigated hydantoins in the ground states were calculated using the density functional method. The relationship between structure and antiproliferative activity was discussed. The data presented in this investigation afford guidelines for the preparation of new hydantoin derivatives with greater antiproliferative activity.
PB  - Springer Wien, Wien
T2  - Monatshefte Fur Chemie
T1  - New derivatives of hydantoin as potential antiproliferative agents: biological and structural characterization in combination with quantum chemical calculations
VL  - 145
IS  - 5
SP  - 821
EP  - 833
DO  - 10.1007/s00706-013-1149-6
ER  - 

@article{
author = "Hmuda, Sleem and Trišović, Nemanja and Rogan, Jelena R. and Poleti, Dejan and Vitnik, Željko and Vitnik, Vesna and Valentić, Nataša V. and Bozic, Biljana and Ušćumlić, Gordana",
year = "2014",
abstract = "Two new series of hydantoin derivatives, 3-(4-substituted benzyl)-5,5-diphenyl- and 3-(4-substituted benzyl)-5-ethyl-5-phenylhydantoins, were synthesized and their antiproliferative activity was tested against human colon cancer HCT-116 and breast cancer MDA-MB-231 cell lines. The presence of different substituents on both hydantoin and benzyl moieties changed the antiproliferative activity of the investigated hydantoins, whereby most of the compounds showed superior antiproliferative activity against MDA-MB-231 than against the HCT-116 cell line. The structure of three compounds was studied by single-crystal X-ray diffraction. The general structural characteristic is the presence of N-H center dot center dot center dot O hydrogen bonds in crystal packings. The molecular geometry and bonding features of the investigated hydantoins in the ground states were calculated using the density functional method. The relationship between structure and antiproliferative activity was discussed. The data presented in this investigation afford guidelines for the preparation of new hydantoin derivatives with greater antiproliferative activity.",
publisher = "Springer Wien, Wien",
journal = "Monatshefte Fur Chemie",
title = "New derivatives of hydantoin as potential antiproliferative agents: biological and structural characterization in combination with quantum chemical calculations",
volume = "145",
number = "5",
pages = "821-833",
doi = "10.1007/s00706-013-1149-6"
}

Hmuda, S., Trišović, N., Rogan, J. R., Poleti, D., Vitnik, Ž., Vitnik, V., Valentić, N. V., Bozic, B.,& Ušćumlić, G.. (2014). New derivatives of hydantoin as potential antiproliferative agents: biological and structural characterization in combination with quantum chemical calculations. in Monatshefte Fur Chemie
Springer Wien, Wien., 145(5), 821-833.
https://doi.org/10.1007/s00706-013-1149-6

Hmuda S, Trišović N, Rogan JR, Poleti D, Vitnik Ž, Vitnik V, Valentić NV, Bozic B, Ušćumlić G. New derivatives of hydantoin as potential antiproliferative agents: biological and structural characterization in combination with quantum chemical calculations. in Monatshefte Fur Chemie. 2014;145(5):821-833.
doi:10.1007/s00706-013-1149-6 .

Hmuda, Sleem, Trišović, Nemanja, Rogan, Jelena R., Poleti, Dejan, Vitnik, Željko, Vitnik, Vesna, Valentić, Nataša V., Bozic, Biljana, Ušćumlić, Gordana, "New derivatives of hydantoin as potential antiproliferative agents: biological and structural characterization in combination with quantum chemical calculations" in Monatshefte Fur Chemie, 145, no. 5 (2014):821-833,
https://doi.org/10.1007/s00706-013-1149-6 . .

TY  - JOUR
AU  - Dostanić, Jasmina
AU  - Mijin, Dušan
AU  - Ušćumlić, Gordana
AU  - Jovanović, Dušan M.
AU  - Zlatar, Matija
AU  - Lončarević, Davor
PY  - 2014
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1512
AB  - A series of 5-(4-substituted arylazo)-6-hydroxy-4-methyl-3-cyano-2-pyridone dyes was synthesized and the structure of the dyes was confirmed by UV-Vis, FT-IR, H-1 NMR and C-13 NMR spectroscopic techniques. The azo-hydrazone tautomeric equilibrium was found to depend on the substituents as well as on the acidity and basicity of the media. Ionization constant, pK(a), of the dyes was determined by UV-Vis spectroscopy and correlated with the Hammett substituent constants, sigma(p) and sigma(I). The interpretation of the effect of different substituent in phenyl ring of arylazo pyridone dyes on their spectroscopic and structural properties was based on quantum chemical calculations performed by the density functional theory (DET/M06-2X) method. The DFT calculations confirmed the existence of two forms in water solution: hydrazone form in acidic and neutral media and anionic form in basic media. The different contribution of azo and hydrazone canonical forms of anionic form is observed for dyes with electron-donating and dyes with electron-withdrawing groups. The dependence of absorption spectra and determined pK(a) values to the substituent type seems to be mostly due to azo/hydrazone canonical structure ratio in their anionic form.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy
T1  - Spectroscopic and quantum chemical investigations of substituent effects on the azo-hydrazone tautomerism and acid-base properties of arylazo pyridone dyes
VL  - 123
SP  - 37
EP  - 45
DO  - 10.1016/j.saa.2013.12.064
ER  - 

@article{
author = "Dostanić, Jasmina and Mijin, Dušan and Ušćumlić, Gordana and Jovanović, Dušan M. and Zlatar, Matija and Lončarević, Davor",
year = "2014",
abstract = "A series of 5-(4-substituted arylazo)-6-hydroxy-4-methyl-3-cyano-2-pyridone dyes was synthesized and the structure of the dyes was confirmed by UV-Vis, FT-IR, H-1 NMR and C-13 NMR spectroscopic techniques. The azo-hydrazone tautomeric equilibrium was found to depend on the substituents as well as on the acidity and basicity of the media. Ionization constant, pK(a), of the dyes was determined by UV-Vis spectroscopy and correlated with the Hammett substituent constants, sigma(p) and sigma(I). The interpretation of the effect of different substituent in phenyl ring of arylazo pyridone dyes on their spectroscopic and structural properties was based on quantum chemical calculations performed by the density functional theory (DET/M06-2X) method. The DFT calculations confirmed the existence of two forms in water solution: hydrazone form in acidic and neutral media and anionic form in basic media. The different contribution of azo and hydrazone canonical forms of anionic form is observed for dyes with electron-donating and dyes with electron-withdrawing groups. The dependence of absorption spectra and determined pK(a) values to the substituent type seems to be mostly due to azo/hydrazone canonical structure ratio in their anionic form.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy",
title = "Spectroscopic and quantum chemical investigations of substituent effects on the azo-hydrazone tautomerism and acid-base properties of arylazo pyridone dyes",
volume = "123",
pages = "37-45",
doi = "10.1016/j.saa.2013.12.064"
}

Dostanić, J., Mijin, D., Ušćumlić, G., Jovanović, D. M., Zlatar, M.,& Lončarević, D.. (2014). Spectroscopic and quantum chemical investigations of substituent effects on the azo-hydrazone tautomerism and acid-base properties of arylazo pyridone dyes. in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy
Oxford : Pergamon-Elsevier Science Ltd., 123, 37-45.
https://doi.org/10.1016/j.saa.2013.12.064

Dostanić J, Mijin D, Ušćumlić G, Jovanović DM, Zlatar M, Lončarević D. Spectroscopic and quantum chemical investigations of substituent effects on the azo-hydrazone tautomerism and acid-base properties of arylazo pyridone dyes. in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy. 2014;123:37-45.
doi:10.1016/j.saa.2013.12.064 .

Dostanić, Jasmina, Mijin, Dušan, Ušćumlić, Gordana, Jovanović, Dušan M., Zlatar, Matija, Lončarević, Davor, "Spectroscopic and quantum chemical investigations of substituent effects on the azo-hydrazone tautomerism and acid-base properties of arylazo pyridone dyes" in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy, 123 (2014):37-45,
https://doi.org/10.1016/j.saa.2013.12.064 . .

TY  - JOUR
AU  - Banjac, Nebojša R.
AU  - Trišović, Nemanja
AU  - Vitnik, Željko
AU  - Vitnik, Vesna
AU  - Valentić, Nataša V.
AU  - Ušćumlić, Gordana
AU  - Juranić, Ivan
PY  - 2013
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1173
AB  - Two series of 1-aryl-3-phenyl- and 1-aryl-3,3-diphenylpyrrolidine-2,5-diones were synthesized and their solvatochromic properties were studied in a set of 15 solvents of different polarity. The effect of specific and non-specific solvent-solute interactions on the position of their absorption bands was evaluated by using the solvent parameter sets of Kamlet and Taft. The interpretation of the effect of different substituent patterns on the solvatochromic properties of the investigated compounds was based on quantum chemical calculations performed by the density functional theory (DFT)/CAM-B3LYP method using the 6-311G(d,p) basis set. The theoretical absorption frequencies show very good agreement with the experimental values. The energy gaps between the HOMO and LUMO orbitals were also analyzed. It is demonstrated that different substituents change the conjugation effect and further determine the pathways of intramolecular charge transfer.
PB  - Springer Wien, Wien
T2  - Monatshefte Fur Chemie
T1  - Solvatochromic and quantum chemical investigations of newly synthesized succinimides: substituent effect on intramolecular charge transfer
VL  - 144
IS  - 10
SP  - 1525
EP  - 1535
DO  - 10.1007/s00706-013-1052-1
ER  - 

@article{
author = "Banjac, Nebojša R. and Trišović, Nemanja and Vitnik, Željko and Vitnik, Vesna and Valentić, Nataša V. and Ušćumlić, Gordana and Juranić, Ivan",
year = "2013",
abstract = "Two series of 1-aryl-3-phenyl- and 1-aryl-3,3-diphenylpyrrolidine-2,5-diones were synthesized and their solvatochromic properties were studied in a set of 15 solvents of different polarity. The effect of specific and non-specific solvent-solute interactions on the position of their absorption bands was evaluated by using the solvent parameter sets of Kamlet and Taft. The interpretation of the effect of different substituent patterns on the solvatochromic properties of the investigated compounds was based on quantum chemical calculations performed by the density functional theory (DFT)/CAM-B3LYP method using the 6-311G(d,p) basis set. The theoretical absorption frequencies show very good agreement with the experimental values. The energy gaps between the HOMO and LUMO orbitals were also analyzed. It is demonstrated that different substituents change the conjugation effect and further determine the pathways of intramolecular charge transfer.",
publisher = "Springer Wien, Wien",
journal = "Monatshefte Fur Chemie",
title = "Solvatochromic and quantum chemical investigations of newly synthesized succinimides: substituent effect on intramolecular charge transfer",
volume = "144",
number = "10",
pages = "1525-1535",
doi = "10.1007/s00706-013-1052-1"
}

Banjac, N. R., Trišović, N., Vitnik, Ž., Vitnik, V., Valentić, N. V., Ušćumlić, G.,& Juranić, I.. (2013). Solvatochromic and quantum chemical investigations of newly synthesized succinimides: substituent effect on intramolecular charge transfer. in Monatshefte Fur Chemie
Springer Wien, Wien., 144(10), 1525-1535.
https://doi.org/10.1007/s00706-013-1052-1

Banjac NR, Trišović N, Vitnik Ž, Vitnik V, Valentić NV, Ušćumlić G, Juranić I. Solvatochromic and quantum chemical investigations of newly synthesized succinimides: substituent effect on intramolecular charge transfer. in Monatshefte Fur Chemie. 2013;144(10):1525-1535.
doi:10.1007/s00706-013-1052-1 .

Banjac, Nebojša R., Trišović, Nemanja, Vitnik, Željko, Vitnik, Vesna, Valentić, Nataša V., Ušćumlić, Gordana, Juranić, Ivan, "Solvatochromic and quantum chemical investigations of newly synthesized succinimides: substituent effect on intramolecular charge transfer" in Monatshefte Fur Chemie, 144, no. 10 (2013):1525-1535,
https://doi.org/10.1007/s00706-013-1052-1 . .

TY  - JOUR
AU  - Alimmari, Adel SA
AU  - Mijin, Dušan
AU  - Vukicevic, Radovan
AU  - Božić, Bojan
AU  - Valentić, Nataša V.
AU  - Vitnik, Vesna
AU  - Vitnik, Željko
AU  - Ušćumlić, Gordana
PY  - 2012
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1048
AB  - Background: A series of some novel arylazo pyridone dyes was synthesized from the corresponding diazonium salt and 6-hydroxy-4-phenyl-3-cyano-2-pyridone using a classical reaction for the synthesis of the azo compounds. Results: The structure of the dyes was confirmed by UV-vis, FT-IR, H-1 NMR and C-13 NMR spectroscopic techniques and elemental analysis. The solvatochromic behavior of the dyes was evaluated with respect to their visible absorption properties in various solvents. Conclusions: The azo-hydrazone tautomeric equilibration was found to depend on the substituents as well as on the solvent. The geometry data of the investigated dyes were obtained using DFT quantum-chemical calculations. The obtained calculational results are in very good agreement with the experimental data.
PB  - BMC
T2  - Chemistry Central Journal
T1  - Synthesis, structure and solvatochromic properties of some novel 5-arylazo-6-hydroxy-4-phenyl-3-cyano-2-pyridone dyes
VL  - 6
DO  - 10.1186/1752-153X-6-71
ER  - 

@article{
author = "Alimmari, Adel SA and Mijin, Dušan and Vukicevic, Radovan and Božić, Bojan and Valentić, Nataša V. and Vitnik, Vesna and Vitnik, Željko and Ušćumlić, Gordana",
year = "2012",
abstract = "Background: A series of some novel arylazo pyridone dyes was synthesized from the corresponding diazonium salt and 6-hydroxy-4-phenyl-3-cyano-2-pyridone using a classical reaction for the synthesis of the azo compounds. Results: The structure of the dyes was confirmed by UV-vis, FT-IR, H-1 NMR and C-13 NMR spectroscopic techniques and elemental analysis. The solvatochromic behavior of the dyes was evaluated with respect to their visible absorption properties in various solvents. Conclusions: The azo-hydrazone tautomeric equilibration was found to depend on the substituents as well as on the solvent. The geometry data of the investigated dyes were obtained using DFT quantum-chemical calculations. The obtained calculational results are in very good agreement with the experimental data.",
publisher = "BMC",
journal = "Chemistry Central Journal",
title = "Synthesis, structure and solvatochromic properties of some novel 5-arylazo-6-hydroxy-4-phenyl-3-cyano-2-pyridone dyes",
volume = "6",
doi = "10.1186/1752-153X-6-71"
}

Alimmari, A. S., Mijin, D., Vukicevic, R., Božić, B., Valentić, N. V., Vitnik, V., Vitnik, Ž.,& Ušćumlić, G.. (2012). Synthesis, structure and solvatochromic properties of some novel 5-arylazo-6-hydroxy-4-phenyl-3-cyano-2-pyridone dyes. in Chemistry Central Journal
BMC., 6.
https://doi.org/10.1186/1752-153X-6-71

Alimmari AS, Mijin D, Vukicevic R, Božić B, Valentić NV, Vitnik V, Vitnik Ž, Ušćumlić G. Synthesis, structure and solvatochromic properties of some novel 5-arylazo-6-hydroxy-4-phenyl-3-cyano-2-pyridone dyes. in Chemistry Central Journal. 2012;6.
doi:10.1186/1752-153X-6-71 .

Alimmari, Adel SA, Mijin, Dušan, Vukicevic, Radovan, Božić, Bojan, Valentić, Nataša V., Vitnik, Vesna, Vitnik, Željko, Ušćumlić, Gordana, "Synthesis, structure and solvatochromic properties of some novel 5-arylazo-6-hydroxy-4-phenyl-3-cyano-2-pyridone dyes" in Chemistry Central Journal, 6 (2012),
https://doi.org/10.1186/1752-153X-6-71 . .

TY  - JOUR
AU  - Božić, Bojan
AU  - Avramov Ivić, Milka
AU  - Trišović, Nemanja
AU  - Petrović, Slobodan D.
AU  - Ušćumlić, Gordana
PY  - 2012
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1065
AB  - As the very first electrochemical investigation of oxaprozin, nonsteroidal anti-inflammatory drug, using cyclic voltammetry on gold electrode in 0.05 mol dm(-3) NaHCO3, the synthesized drug, its analytical standard and its content in Duraprox (R) tablets were characterized with one oxidation reaction and the three reduction reactions. All they exhibited the linear concentration dependency of anodic currents at 0.83V for the analytical standard and 0.85V for Duraprox (R) tablets in the range of concentrations 8.44 - 32.78x10(-6) mol dm(-3). The strong adsorption of bovine serum albumin (BSA) on gold electrode in 0.1 mol dm(-3) phosphate buffer solution (pH 7.4) is shown and concentration dependency of anodic currents of oxaprozin standard on BSA/Au is studied. Following the Langmuir adsorption thermodynamic equation, the binding constants of oxaprozin on BSA/Au electrode was calculated with the results 1.23x10(5) dm(3) mol(-1).
PB  - Esg, Belgrade
T2  - International Journal of Electrochemical Science
T1  - Electrochemical Characterization of Oxaprozin on Bare Gold Electrode and Electrode Modified with Bovine Serum Albumin
VL  - 7
IS  - 11
SP  - 11609
EP  - 11616
UR  - https://hdl.handle.net/21.15107/rcub_cer_1065
ER  - 

@article{
author = "Božić, Bojan and Avramov Ivić, Milka and Trišović, Nemanja and Petrović, Slobodan D. and Ušćumlić, Gordana",
year = "2012",
abstract = "As the very first electrochemical investigation of oxaprozin, nonsteroidal anti-inflammatory drug, using cyclic voltammetry on gold electrode in 0.05 mol dm(-3) NaHCO3, the synthesized drug, its analytical standard and its content in Duraprox (R) tablets were characterized with one oxidation reaction and the three reduction reactions. All they exhibited the linear concentration dependency of anodic currents at 0.83V for the analytical standard and 0.85V for Duraprox (R) tablets in the range of concentrations 8.44 - 32.78x10(-6) mol dm(-3). The strong adsorption of bovine serum albumin (BSA) on gold electrode in 0.1 mol dm(-3) phosphate buffer solution (pH 7.4) is shown and concentration dependency of anodic currents of oxaprozin standard on BSA/Au is studied. Following the Langmuir adsorption thermodynamic equation, the binding constants of oxaprozin on BSA/Au electrode was calculated with the results 1.23x10(5) dm(3) mol(-1).",
publisher = "Esg, Belgrade",
journal = "International Journal of Electrochemical Science",
title = "Electrochemical Characterization of Oxaprozin on Bare Gold Electrode and Electrode Modified with Bovine Serum Albumin",
volume = "7",
number = "11",
pages = "11609-11616",
url = "https://hdl.handle.net/21.15107/rcub_cer_1065"
}

Božić, B., Avramov Ivić, M., Trišović, N., Petrović, S. D.,& Ušćumlić, G.. (2012). Electrochemical Characterization of Oxaprozin on Bare Gold Electrode and Electrode Modified with Bovine Serum Albumin. in International Journal of Electrochemical Science
Esg, Belgrade., 7(11), 11609-11616.
https://hdl.handle.net/21.15107/rcub_cer_1065

Božić B, Avramov Ivić M, Trišović N, Petrović SD, Ušćumlić G. Electrochemical Characterization of Oxaprozin on Bare Gold Electrode and Electrode Modified with Bovine Serum Albumin. in International Journal of Electrochemical Science. 2012;7(11):11609-11616.
https://hdl.handle.net/21.15107/rcub_cer_1065 .

Božić, Bojan, Avramov Ivić, Milka, Trišović, Nemanja, Petrović, Slobodan D., Ušćumlić, Gordana, "Electrochemical Characterization of Oxaprozin on Bare Gold Electrode and Electrode Modified with Bovine Serum Albumin" in International Journal of Electrochemical Science, 7, no. 11 (2012):11609-11616,
https://hdl.handle.net/21.15107/rcub_cer_1065 .

TY  - JOUR
AU  - Dostanić, Jasmina
AU  - Valentić, Nataša V.
AU  - Ušćumlić, Gordana
AU  - Mijin, Dušan
PY  - 2011
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/886
AB  - A new procedure for the synthesis of known azo pyridone dyes is presented. A series of 5-(substituted arylazo)-6-hydroxy-4-methyl-3-cyano-2-pyridones were prepared from ethyl 3-oxo-2-(substituted phenylazo)butanoates and cyanoacetamide in acetone using potassium hydroxide as a catalyst by simple refluxing the reaction mixture. The structure of these dyes was confirmed by FT-IR, NMR and UV-Vis spectroscopy.
AB  - Novi postupak za sintezu poznatih azo-piridonskih boja je opisan u radu. Serija 5-(supstituisanih fenilazo)-6-hidroksi-4-metil-3-cijano-2-piridona je pripremljena iz etil-3-okso-2-(supstituisanih fenilazo)butanoata i cijanoacetamida u acetonu korišćenjem kalijum-hidroksida kao katalizatora uz zagrevanje.
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Synthesis of 5-(substituted phenylazo)-6-hydroxy-4-methyl-3-cyano-2-pyridones from ethyl 3-oxo-2-(substituted phenylazo)butanoates
T1  - Sinteza 5-(supstituisanih fenilazo)-6-hidroksi-4-metil-3-cijano-2-piridona iz etil-3-okso-2-(supstituisanih fenilazo)butanoata
VL  - 76
IS  - 4
SP  - 499
EP  - 504
DO  - 10.2298/JSC100618044D
ER  - 

@article{
author = "Dostanić, Jasmina and Valentić, Nataša V. and Ušćumlić, Gordana and Mijin, Dušan",
year = "2011",
abstract = "A new procedure for the synthesis of known azo pyridone dyes is presented. A series of 5-(substituted arylazo)-6-hydroxy-4-methyl-3-cyano-2-pyridones were prepared from ethyl 3-oxo-2-(substituted phenylazo)butanoates and cyanoacetamide in acetone using potassium hydroxide as a catalyst by simple refluxing the reaction mixture. The structure of these dyes was confirmed by FT-IR, NMR and UV-Vis spectroscopy., Novi postupak za sintezu poznatih azo-piridonskih boja je opisan u radu. Serija 5-(supstituisanih fenilazo)-6-hidroksi-4-metil-3-cijano-2-piridona je pripremljena iz etil-3-okso-2-(supstituisanih fenilazo)butanoata i cijanoacetamida u acetonu korišćenjem kalijum-hidroksida kao katalizatora uz zagrevanje.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Synthesis of 5-(substituted phenylazo)-6-hydroxy-4-methyl-3-cyano-2-pyridones from ethyl 3-oxo-2-(substituted phenylazo)butanoates, Sinteza 5-(supstituisanih fenilazo)-6-hidroksi-4-metil-3-cijano-2-piridona iz etil-3-okso-2-(supstituisanih fenilazo)butanoata",
volume = "76",
number = "4",
pages = "499-504",
doi = "10.2298/JSC100618044D"
}

Dostanić, J., Valentić, N. V., Ušćumlić, G.,& Mijin, D.. (2011). Synthesis of 5-(substituted phenylazo)-6-hydroxy-4-methyl-3-cyano-2-pyridones from ethyl 3-oxo-2-(substituted phenylazo)butanoates. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 76(4), 499-504.
https://doi.org/10.2298/JSC100618044D

Dostanić J, Valentić NV, Ušćumlić G, Mijin D. Synthesis of 5-(substituted phenylazo)-6-hydroxy-4-methyl-3-cyano-2-pyridones from ethyl 3-oxo-2-(substituted phenylazo)butanoates. in Journal of the Serbian Chemical Society. 2011;76(4):499-504.
doi:10.2298/JSC100618044D .

Dostanić, Jasmina, Valentić, Nataša V., Ušćumlić, Gordana, Mijin, Dušan, "Synthesis of 5-(substituted phenylazo)-6-hydroxy-4-methyl-3-cyano-2-pyridones from ethyl 3-oxo-2-(substituted phenylazo)butanoates" in Journal of the Serbian Chemical Society, 76, no. 4 (2011):499-504,
https://doi.org/10.2298/JSC100618044D . .

TY  - JOUR
AU  - Alimmari, Adel SA
AU  - Marinković, Aleksandar D.
AU  - Mijin, Dušan
AU  - Valentić, Nataša V.
AU  - Todorović, Nina
AU  - Ušćumlić, Gordana
PY  - 2010
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/712
AB  - A series of some new pyridone arylazo dyes was synthesized from the corresponding diazonium salts and 3-cyano-4,6-diphenyl-2-pyridone using the classical reaction for the synthesis of the azo compounds. The structures of these dyes were confirmed by UV-Vis, FT-IR and 1H-NMR spectroscopic techniques. The solvatochromism of the dyes was evaluated with respect to visible absorption properties in various solvents. The effects of solvent dipolarity/polarizability and solvent/solute hydrogen bonding interactions were analyzed by means of the linear solvation energy relationship concept proposed by Kamlet and Taft. The 2-pyridone/2-hydroxypiridine tautomeric equilibration was found to depend on the substituents as well as on the solvents.
AB  - Serija novih piridonskih arilazo boja je sintetisana reakcijom odgovarajućih diazonijum soli i 3-cijano-4,6-difenil-2-piridona primenom klasične sinteze azo jedinjenja. Struktura sintetisanih boja je potvrđena na osnovu podataka dobijenih iz UV, FT-IR i 1H-NMR spektara. Solvatohromna svojstva boja su procenjena u odnosu na njihovu apsorpciju u vidljivom delu spektra u različitim rastvračima. Efekti rastvarača, dipolarnost/polarizabilnost i vodonične interakcije rastvarač/rastvorak, su analizirane primenom linearne korelacije solvatohromnih efekata predložene od strane Kamlet-a i Taft-a. Tautomerna ravnoteža 2-piridon/2-hidroksipiridin zavisi kako od efekata supstituenta tako i od uticaja rastvarača.
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Synthesis, structure and solvatochromic properties of 3-cyano-4,6-diphenyl-5-(3- and 4-substituted phenylazo)-2-pyridones
T1  - Sinteza, struktura i solvatohromna svojstva 3-cijano-4,6-difenil-5-(3- i 4-supstituisanih fenilazo)-2-piridona
VL  - 75
IS  - 8
SP  - 1019
EP  - 1032
DO  - 10.2298/JSC091009074A
ER  - 

@article{
author = "Alimmari, Adel SA and Marinković, Aleksandar D. and Mijin, Dušan and Valentić, Nataša V. and Todorović, Nina and Ušćumlić, Gordana",
year = "2010",
abstract = "A series of some new pyridone arylazo dyes was synthesized from the corresponding diazonium salts and 3-cyano-4,6-diphenyl-2-pyridone using the classical reaction for the synthesis of the azo compounds. The structures of these dyes were confirmed by UV-Vis, FT-IR and 1H-NMR spectroscopic techniques. The solvatochromism of the dyes was evaluated with respect to visible absorption properties in various solvents. The effects of solvent dipolarity/polarizability and solvent/solute hydrogen bonding interactions were analyzed by means of the linear solvation energy relationship concept proposed by Kamlet and Taft. The 2-pyridone/2-hydroxypiridine tautomeric equilibration was found to depend on the substituents as well as on the solvents., Serija novih piridonskih arilazo boja je sintetisana reakcijom odgovarajućih diazonijum soli i 3-cijano-4,6-difenil-2-piridona primenom klasične sinteze azo jedinjenja. Struktura sintetisanih boja je potvrđena na osnovu podataka dobijenih iz UV, FT-IR i 1H-NMR spektara. Solvatohromna svojstva boja su procenjena u odnosu na njihovu apsorpciju u vidljivom delu spektra u različitim rastvračima. Efekti rastvarača, dipolarnost/polarizabilnost i vodonične interakcije rastvarač/rastvorak, su analizirane primenom linearne korelacije solvatohromnih efekata predložene od strane Kamlet-a i Taft-a. Tautomerna ravnoteža 2-piridon/2-hidroksipiridin zavisi kako od efekata supstituenta tako i od uticaja rastvarača.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Synthesis, structure and solvatochromic properties of 3-cyano-4,6-diphenyl-5-(3- and 4-substituted phenylazo)-2-pyridones, Sinteza, struktura i solvatohromna svojstva 3-cijano-4,6-difenil-5-(3- i 4-supstituisanih fenilazo)-2-piridona",
volume = "75",
number = "8",
pages = "1019-1032",
doi = "10.2298/JSC091009074A"
}

Alimmari, A. S., Marinković, A. D., Mijin, D., Valentić, N. V., Todorović, N.,& Ušćumlić, G.. (2010). Synthesis, structure and solvatochromic properties of 3-cyano-4,6-diphenyl-5-(3- and 4-substituted phenylazo)-2-pyridones. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 75(8), 1019-1032.
https://doi.org/10.2298/JSC091009074A

Alimmari AS, Marinković AD, Mijin D, Valentić NV, Todorović N, Ušćumlić G. Synthesis, structure and solvatochromic properties of 3-cyano-4,6-diphenyl-5-(3- and 4-substituted phenylazo)-2-pyridones. in Journal of the Serbian Chemical Society. 2010;75(8):1019-1032.
doi:10.2298/JSC091009074A .

Alimmari, Adel SA, Marinković, Aleksandar D., Mijin, Dušan, Valentić, Nataša V., Todorović, Nina, Ušćumlić, Gordana, "Synthesis, structure and solvatochromic properties of 3-cyano-4,6-diphenyl-5-(3- and 4-substituted phenylazo)-2-pyridones" in Journal of the Serbian Chemical Society, 75, no. 8 (2010):1019-1032,
https://doi.org/10.2298/JSC091009074A . .

TY  - JOUR
AU  - Valentić, Nataša V.
AU  - Vitnik, Željko
AU  - Mijin, Dušan
AU  - Ušćumlić, Gordana
AU  - Todorović, Nina
AU  - Juranić, Ivan
PY  - 2009
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3994
AB  - The C-13 NMR chemical shifts of the C2 carbon atom in the heteroaromatic nuclei of seventeen 5-(3- and 4-substituted arylazo)-4,6-dimethyl-3-cyano-2-pyridones were determined in deuterated DMSO solution. For quantitative assessment of the substituent effects on the C-13 NMR chemical shifts simple and extended Hammett equations and Swain-Lupton equation were used. The mode of transmission of substituent effects have been discussed in a relation to the geometry of investigated molecules. The geometry data were obtained using semiempirical MNDO-PM6 energy calculations. The observed C-13 NMR substituent chemical shifts were correlated with literature C-13 NMR data for the corresponding 3- and 4-substituted- 2',6'-dimethylazobenzenes and 3- and 4-substituted azobenzenes. A good linear dependence obtained in this way, provided a basis to discuss the influence of the ortho-methyl groups on the degree of coplanarity of azobenzene and pyridone systems, and on the efficiency of transmission of electronic substituent effect from one ring to the other one.
PB  - Arkat USA Inc.
T2  - ARKIVOC - Online Journal of Organic Chemistry
T1  - Linear Free Energy Relationships of the C-13 NMR chemical shifts in 5-(3-and 4-substituted arylazo)-4,6-dimethyl-3-cyano-2-pyridones
VL  - 2009
IS  - 13
SP  - 227
EP  - 240
DO  - 10.3998/ark.5550190.0010.d20
ER  - 

@article{
author = "Valentić, Nataša V. and Vitnik, Željko and Mijin, Dušan and Ušćumlić, Gordana and Todorović, Nina and Juranić, Ivan",
year = "2009",
abstract = "The C-13 NMR chemical shifts of the C2 carbon atom in the heteroaromatic nuclei of seventeen 5-(3- and 4-substituted arylazo)-4,6-dimethyl-3-cyano-2-pyridones were determined in deuterated DMSO solution. For quantitative assessment of the substituent effects on the C-13 NMR chemical shifts simple and extended Hammett equations and Swain-Lupton equation were used. The mode of transmission of substituent effects have been discussed in a relation to the geometry of investigated molecules. The geometry data were obtained using semiempirical MNDO-PM6 energy calculations. The observed C-13 NMR substituent chemical shifts were correlated with literature C-13 NMR data for the corresponding 3- and 4-substituted- 2',6'-dimethylazobenzenes and 3- and 4-substituted azobenzenes. A good linear dependence obtained in this way, provided a basis to discuss the influence of the ortho-methyl groups on the degree of coplanarity of azobenzene and pyridone systems, and on the efficiency of transmission of electronic substituent effect from one ring to the other one.",
publisher = "Arkat USA Inc.",
journal = "ARKIVOC - Online Journal of Organic Chemistry",
title = "Linear Free Energy Relationships of the C-13 NMR chemical shifts in 5-(3-and 4-substituted arylazo)-4,6-dimethyl-3-cyano-2-pyridones",
volume = "2009",
number = "13",
pages = "227-240",
doi = "10.3998/ark.5550190.0010.d20"
}

Valentić, N. V., Vitnik, Ž., Mijin, D., Ušćumlić, G., Todorović, N.,& Juranić, I.. (2009). Linear Free Energy Relationships of the C-13 NMR chemical shifts in 5-(3-and 4-substituted arylazo)-4,6-dimethyl-3-cyano-2-pyridones. in ARKIVOC - Online Journal of Organic Chemistry
Arkat USA Inc.., 2009(13), 227-240.
https://doi.org/10.3998/ark.5550190.0010.d20

Valentić NV, Vitnik Ž, Mijin D, Ušćumlić G, Todorović N, Juranić I. Linear Free Energy Relationships of the C-13 NMR chemical shifts in 5-(3-and 4-substituted arylazo)-4,6-dimethyl-3-cyano-2-pyridones. in ARKIVOC - Online Journal of Organic Chemistry. 2009;2009(13):227-240.
doi:10.3998/ark.5550190.0010.d20 .

Valentić, Nataša V., Vitnik, Željko, Mijin, Dušan, Ušćumlić, Gordana, Todorović, Nina, Juranić, Ivan, "Linear Free Energy Relationships of the C-13 NMR chemical shifts in 5-(3-and 4-substituted arylazo)-4,6-dimethyl-3-cyano-2-pyridones" in ARKIVOC - Online Journal of Organic Chemistry, 2009, no. 13 (2009):227-240,
https://doi.org/10.3998/ark.5550190.0010.d20 . .