TY  - JOUR
AU  - Bondžić, Bojan
AU  - Daskalakis, Konstantinos
AU  - Taniguchi, Tohru
AU  - Monde, Kenji
AU  - Hayashi, Yujiro
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5417
AB  - A catalytic, asymmetric Diels-Alder reaction of α-fluoro α,β-unsaturated aldehydes and cyclopentadiene was developed using diarylprolinol silyl ether as an organocatalyst. The reaction proceeds in toluene with trifluoroacetic acid as an additive (condition A). Perchloric acid salt of diarylprolinol silyl ether also promotes the reaction using water as a reaction medium (condition B). In both cases, excellent exo-selectivity and enantioselectivity were obtained with generation of a fluorinated quaternary chiral center.
PB  - USA : American Chemical Society
T2  - Organic Letters
T1  - Stereoselective Construction of Fluorinated Quaternary Stereogenic Centers via an Organocatalytic Asymmetric exo-Selective Diels-Alder Reaction in the Presence of Water
VL  - 24
IS  - 40
SP  - 7455
EP  - 7460
DO  - 10.1021/acs.orglett.2c03043
ER  - 

@article{
author = "Bondžić, Bojan and Daskalakis, Konstantinos and Taniguchi, Tohru and Monde, Kenji and Hayashi, Yujiro",
year = "2022",
abstract = "A catalytic, asymmetric Diels-Alder reaction of α-fluoro α,β-unsaturated aldehydes and cyclopentadiene was developed using diarylprolinol silyl ether as an organocatalyst. The reaction proceeds in toluene with trifluoroacetic acid as an additive (condition A). Perchloric acid salt of diarylprolinol silyl ether also promotes the reaction using water as a reaction medium (condition B). In both cases, excellent exo-selectivity and enantioselectivity were obtained with generation of a fluorinated quaternary chiral center.",
publisher = "USA : American Chemical Society",
journal = "Organic Letters",
title = "Stereoselective Construction of Fluorinated Quaternary Stereogenic Centers via an Organocatalytic Asymmetric exo-Selective Diels-Alder Reaction in the Presence of Water",
volume = "24",
number = "40",
pages = "7455-7460",
doi = "10.1021/acs.orglett.2c03043"
}

Bondžić, B., Daskalakis, K., Taniguchi, T., Monde, K.,& Hayashi, Y.. (2022). Stereoselective Construction of Fluorinated Quaternary Stereogenic Centers via an Organocatalytic Asymmetric exo-Selective Diels-Alder Reaction in the Presence of Water. in Organic Letters
USA : American Chemical Society., 24(40), 7455-7460.
https://doi.org/10.1021/acs.orglett.2c03043

Bondžić B, Daskalakis K, Taniguchi T, Monde K, Hayashi Y. Stereoselective Construction of Fluorinated Quaternary Stereogenic Centers via an Organocatalytic Asymmetric exo-Selective Diels-Alder Reaction in the Presence of Water. in Organic Letters. 2022;24(40):7455-7460.
doi:10.1021/acs.orglett.2c03043 .

Bondžić, Bojan, Daskalakis, Konstantinos, Taniguchi, Tohru, Monde, Kenji, Hayashi, Yujiro, "Stereoselective Construction of Fluorinated Quaternary Stereogenic Centers via an Organocatalytic Asymmetric exo-Selective Diels-Alder Reaction in the Presence of Water" in Organic Letters, 24, no. 40 (2022):7455-7460,
https://doi.org/10.1021/acs.orglett.2c03043 . .

TY  - JOUR
AU  - Bondžić, Aleksandra
AU  - Senćanski, Milan
AU  - Vujačić Nikezić, Ana V.
AU  - Kirillova, Marina V.
AU  - André, Vânia
AU  - Kirillov, Alexander M.
AU  - Bondžić, Bojan
PY  - 2020
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3958
AB  - Three coordination compounds featuring different types of tetracopper(II) cores, namely
[O⊂Cu4{N(CH2CH2O)3}4(BOH)4][BF4]2 (1), [Cu4(μ4-H2edte)(μ5-H2edte)(sal)2]n·7nH2O, (H4edte=N,N,N′,
N′-tetrakis(2-hydroxyethyl)ethylenediamine, H2sal=salicylic acid) (2), and [{Cu4(μ3-Hbes)4(μ-hba)}K
(H2O)3]n, H3bes=N,N-bis(2-hydroxyethyl)-2-aminoethanesulfonic acid (3), were assayed for their potency to
inhibit the acetyl (AChE) and butyrylcholinesterase (BuChE) enzymes aiming to test these compounds as potential
dual inhibitors in the treatment of Alzheimer's disease. All the investigated compounds showed a strong
inhibitory potency toward both enzymes with IC50 values in micromolar range of concentration; compound 1
displayed the most potent inhibitory behaviour toward both enzymes. The mechanism of the AChE and BuChE
inhibition was examined by enzyme kinetic measurements. The obtained kinetic parameters, Vmax and Km indicated
an uncompetitive type of inhibition of both enzymes by compound 1. For the other two compounds a
non-competitive inhibition mode was observed. To get further insight into the mechanism of action and to
elucidate binding modes in details we examined the interactions of 1–3 with acetylcholinesterase, using molecular
docking approach. Grid based docking studies indicated that these compounds can bind to peripheral
anionic site (PAS) of the AChE with Ki values in micromolar range. Moreover, blind docking revealed the
capability of investigated compounds to bind to new allosteric site (i.e. binding site II) distinct from PAS.
Showing that these Cu-based compounds can act as new allosteric inhibitors of AChE and identifying novel
allosteric binding site on AChE represents a significant contribution toward the design of novel and more
effective inhibitors of AChE.
PB  - Elsevier
T2  - Journal of Inorganic Biochemistry
T1  - Aminoalcoholate-driven tetracopper(II) cores as dual acetyl and butyrylcholinesterase inhibitors: Experimental and theoretical elucidation of mechanism of action
VL  - 205
SP  - 110990
DO  - 10.1016/j.jinorgbio.2019.110990
ER  - 

@article{
author = "Bondžić, Aleksandra and Senćanski, Milan and Vujačić Nikezić, Ana V. and Kirillova, Marina V. and André, Vânia and Kirillov, Alexander M. and Bondžić, Bojan",
year = "2020",
abstract = "Three coordination compounds featuring different types of tetracopper(II) cores, namely
[O⊂Cu4{N(CH2CH2O)3}4(BOH)4][BF4]2 (1), [Cu4(μ4-H2edte)(μ5-H2edte)(sal)2]n·7nH2O, (H4edte=N,N,N′,
N′-tetrakis(2-hydroxyethyl)ethylenediamine, H2sal=salicylic acid) (2), and [{Cu4(μ3-Hbes)4(μ-hba)}K
(H2O)3]n, H3bes=N,N-bis(2-hydroxyethyl)-2-aminoethanesulfonic acid (3), were assayed for their potency to
inhibit the acetyl (AChE) and butyrylcholinesterase (BuChE) enzymes aiming to test these compounds as potential
dual inhibitors in the treatment of Alzheimer's disease. All the investigated compounds showed a strong
inhibitory potency toward both enzymes with IC50 values in micromolar range of concentration; compound 1
displayed the most potent inhibitory behaviour toward both enzymes. The mechanism of the AChE and BuChE
inhibition was examined by enzyme kinetic measurements. The obtained kinetic parameters, Vmax and Km indicated
an uncompetitive type of inhibition of both enzymes by compound 1. For the other two compounds a
non-competitive inhibition mode was observed. To get further insight into the mechanism of action and to
elucidate binding modes in details we examined the interactions of 1–3 with acetylcholinesterase, using molecular
docking approach. Grid based docking studies indicated that these compounds can bind to peripheral
anionic site (PAS) of the AChE with Ki values in micromolar range. Moreover, blind docking revealed the
capability of investigated compounds to bind to new allosteric site (i.e. binding site II) distinct from PAS.
Showing that these Cu-based compounds can act as new allosteric inhibitors of AChE and identifying novel
allosteric binding site on AChE represents a significant contribution toward the design of novel and more
effective inhibitors of AChE.",
publisher = "Elsevier",
journal = "Journal of Inorganic Biochemistry",
title = "Aminoalcoholate-driven tetracopper(II) cores as dual acetyl and butyrylcholinesterase inhibitors: Experimental and theoretical elucidation of mechanism of action",
volume = "205",
pages = "110990",
doi = "10.1016/j.jinorgbio.2019.110990"
}

Bondžić, A., Senćanski, M., Vujačić Nikezić, A. V., Kirillova, M. V., André, V., Kirillov, A. M.,& Bondžić, B.. (2020). Aminoalcoholate-driven tetracopper(II) cores as dual acetyl and butyrylcholinesterase inhibitors: Experimental and theoretical elucidation of mechanism of action. in Journal of Inorganic Biochemistry
Elsevier., 205, 110990.
https://doi.org/10.1016/j.jinorgbio.2019.110990

Bondžić A, Senćanski M, Vujačić Nikezić AV, Kirillova MV, André V, Kirillov AM, Bondžić B. Aminoalcoholate-driven tetracopper(II) cores as dual acetyl and butyrylcholinesterase inhibitors: Experimental and theoretical elucidation of mechanism of action. in Journal of Inorganic Biochemistry. 2020;205:110990.
doi:10.1016/j.jinorgbio.2019.110990 .

Bondžić, Aleksandra, Senćanski, Milan, Vujačić Nikezić, Ana V., Kirillova, Marina V., André, Vânia, Kirillov, Alexander M., Bondžić, Bojan, "Aminoalcoholate-driven tetracopper(II) cores as dual acetyl and butyrylcholinesterase inhibitors: Experimental and theoretical elucidation of mechanism of action" in Journal of Inorganic Biochemistry, 205 (2020):110990,
https://doi.org/10.1016/j.jinorgbio.2019.110990 . .

TY  - JOUR
AU  - Baranac-Stojanović, Marija
AU  - Stojanović, Milovan
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2945
AB  - This work was initiated by the increasing interest in BN/CC isosterism and by the long-lasting interest in the concepts of aromaticity and substituent effects. We have theoretically examined the aromaticity and stability of monosubstituted BN isosters of benzene, the three isomeric azaborines. The results provide insight into the effect of substitution on two basic molecular properties, which are influenced, here, by the substituent effects and by the B/N relationship in the ring. The results, along with other examples in the literature, also warn chemists that the general belief that aromaticity accounts for enhanced thermodynamic stability is not always true. The stability of cyclic, conjugated compounds depends on several effects, and only one of them is aromaticity. In addition, our calculations predict a switching of electronic properties of the NH2 group from the usual p-electron donor to a p-electron acceptor when it is moved from the B/C atoms to the nitrogen atom in all isomers, or C6 in 1,3-azaborine. This is the result of the conformational change that places the NLP in the plane of the ring and the NH bonds in a favourable spatial position to act as acceptors of p-electron density
PB  - Royal Society of Chemistry (RSC)
T2  - Physical Chemistry Chemical Physics
T1  - Does aromaticity account for an enhanced thermodynamic stability? The case of monosubstituted azaborines and the stereoelectronic chameleonism of the NH2 group
VL  - 21
IS  - 18
SP  - 9465
EP  - 9476
DO  - 10.1039/C9CP01011D
ER  - 

@article{
author = "Baranac-Stojanović, Marija and Stojanović, Milovan",
year = "2019",
abstract = "This work was initiated by the increasing interest in BN/CC isosterism and by the long-lasting interest in the concepts of aromaticity and substituent effects. We have theoretically examined the aromaticity and stability of monosubstituted BN isosters of benzene, the three isomeric azaborines. The results provide insight into the effect of substitution on two basic molecular properties, which are influenced, here, by the substituent effects and by the B/N relationship in the ring. The results, along with other examples in the literature, also warn chemists that the general belief that aromaticity accounts for enhanced thermodynamic stability is not always true. The stability of cyclic, conjugated compounds depends on several effects, and only one of them is aromaticity. In addition, our calculations predict a switching of electronic properties of the NH2 group from the usual p-electron donor to a p-electron acceptor when it is moved from the B/C atoms to the nitrogen atom in all isomers, or C6 in 1,3-azaborine. This is the result of the conformational change that places the NLP in the plane of the ring and the NH bonds in a favourable spatial position to act as acceptors of p-electron density",
publisher = "Royal Society of Chemistry (RSC)",
journal = "Physical Chemistry Chemical Physics",
title = "Does aromaticity account for an enhanced thermodynamic stability? The case of monosubstituted azaborines and the stereoelectronic chameleonism of the NH2 group",
volume = "21",
number = "18",
pages = "9465-9476",
doi = "10.1039/C9CP01011D"
}

Baranac-Stojanović, M.,& Stojanović, M.. (2019). Does aromaticity account for an enhanced thermodynamic stability? The case of monosubstituted azaborines and the stereoelectronic chameleonism of the NH2 group. in Physical Chemistry Chemical Physics
Royal Society of Chemistry (RSC)., 21(18), 9465-9476.
https://doi.org/10.1039/C9CP01011D

Baranac-Stojanović M, Stojanović M. Does aromaticity account for an enhanced thermodynamic stability? The case of monosubstituted azaborines and the stereoelectronic chameleonism of the NH2 group. in Physical Chemistry Chemical Physics. 2019;21(18):9465-9476.
doi:10.1039/C9CP01011D .

Baranac-Stojanović, Marija, Stojanović, Milovan, "Does aromaticity account for an enhanced thermodynamic stability? The case of monosubstituted azaborines and the stereoelectronic chameleonism of the NH2 group" in Physical Chemistry Chemical Physics, 21, no. 18 (2019):9465-9476,
https://doi.org/10.1039/C9CP01011D . .

TY  - JOUR
AU  - Baranac-Stojanović, Marija
AU  - Stojanović, Milovan
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2946
AB  - This work was initiated by the increasing interest in BN/CC isosterism and by the long-lasting interest in the concepts of aromaticity and substituent effects. We have theoretically examined the aromaticity and stability of monosubstituted BN isosters of benzene, the three isomeric azaborines. The results provide insight into the effect of substitution on two basic molecular properties, which are influenced, here, by the substituent effects and by the B/N relationship in the ring. The results, along with other examples in the literature, also warn chemists that the general belief that aromaticity accounts for enhanced thermodynamic stability is not always true. The stability of cyclic, conjugated compounds depends on several effects, and only one of them is aromaticity. In addition, our calculations predict a switching of electronic properties of the NH2 group from the usual p-electron donor to a p-electron acceptor when it is moved from the B/C atoms to the nitrogen atom in all isomers, or C6 in 1,3-azaborine. This is the result of the conformational change that places the NLP in the plane of the ring and the NH bonds in a favourable spatial position to act as acceptors of p-electron density
PB  - Royal Society of Chemistry (RSC)
T2  - Physical Chemistry Chemical Physics
T1  - Does aromaticity account for an enhanced thermodynamic stability? The case of monosubstituted azaborines and the stereoelectronic chameleonism of the NH2 group
VL  - 21
IS  - 18
SP  - 9465
EP  - 9476
DO  - 10.1039/C9CP01011D
ER  - 

@article{
author = "Baranac-Stojanović, Marija and Stojanović, Milovan",
year = "2019",
abstract = "This work was initiated by the increasing interest in BN/CC isosterism and by the long-lasting interest in the concepts of aromaticity and substituent effects. We have theoretically examined the aromaticity and stability of monosubstituted BN isosters of benzene, the three isomeric azaborines. The results provide insight into the effect of substitution on two basic molecular properties, which are influenced, here, by the substituent effects and by the B/N relationship in the ring. The results, along with other examples in the literature, also warn chemists that the general belief that aromaticity accounts for enhanced thermodynamic stability is not always true. The stability of cyclic, conjugated compounds depends on several effects, and only one of them is aromaticity. In addition, our calculations predict a switching of electronic properties of the NH2 group from the usual p-electron donor to a p-electron acceptor when it is moved from the B/C atoms to the nitrogen atom in all isomers, or C6 in 1,3-azaborine. This is the result of the conformational change that places the NLP in the plane of the ring and the NH bonds in a favourable spatial position to act as acceptors of p-electron density",
publisher = "Royal Society of Chemistry (RSC)",
journal = "Physical Chemistry Chemical Physics",
title = "Does aromaticity account for an enhanced thermodynamic stability? The case of monosubstituted azaborines and the stereoelectronic chameleonism of the NH2 group",
volume = "21",
number = "18",
pages = "9465-9476",
doi = "10.1039/C9CP01011D"
}

Baranac-Stojanović, M.,& Stojanović, M.. (2019). Does aromaticity account for an enhanced thermodynamic stability? The case of monosubstituted azaborines and the stereoelectronic chameleonism of the NH2 group. in Physical Chemistry Chemical Physics
Royal Society of Chemistry (RSC)., 21(18), 9465-9476.
https://doi.org/10.1039/C9CP01011D

Baranac-Stojanović M, Stojanović M. Does aromaticity account for an enhanced thermodynamic stability? The case of monosubstituted azaborines and the stereoelectronic chameleonism of the NH2 group. in Physical Chemistry Chemical Physics. 2019;21(18):9465-9476.
doi:10.1039/C9CP01011D .

Baranac-Stojanović, Marija, Stojanović, Milovan, "Does aromaticity account for an enhanced thermodynamic stability? The case of monosubstituted azaborines and the stereoelectronic chameleonism of the NH2 group" in Physical Chemistry Chemical Physics, 21, no. 18 (2019):9465-9476,
https://doi.org/10.1039/C9CP01011D . .

TY  - JOUR
AU  - Baranac-Stojanović, Marija
AU  - Stojanović, Milovan
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2960
AB  - The effect of two types of dibenzo-fusion of pentalene in the singlet and triplet states on its molecular energies and magnetically induced ring currents was examined via density functional calculations. The isomerization energy decomposition analysis (IEDA) together with the calculated aromaticity indices (NICS(1) zz , HOMA and FLU π ), estimation of resonance energies (RE) and extra cyclic resonance energies (ECRE) via the NBO method, and the NICS-XY-scans revealed that the π-electronic system is the most important factor controlling the molecular energies. The [a,f] topology features greater delocalization, which results in two opposing effects: larger ECRE, but weaker π-bonding. The latter is mainly responsible for the higher energy of [a,f]-dibenzopentalene (DBP) (ΔE iso = 21.7 kcal mol -1 ), with the other effects being σ-orbital and electrostatic interactions. The reversal of energetic stability in the triplet states (ΔE iso = -10.8 kcal mol -1 ) mainly comes from the reduced Pauli repulsion in [a,f]-DBP, which stabilizes the unpaired spin density over the central trimethylenemethane subunit vs. the central pentalene subunit in [a,e]-DBP. Although the [a,e] topology only reduces the diatropic and paratropic currents of the elementary subunits, benzene and pentalene, the [a,f] topology also creates strong global paratropicity involving the benzene rings. Both DBP isomers are characterized by global and smaller semi-global and local diatropic currents in the triplet state.
PB  - Royal Society of Chemistry
T2  - Physical Chemistry Chemical Physics
T1  - The effect of two types of dibenzoannulation of pentalene on molecular energies and magnetically induced currents
VL  - 21
IS  - 6
SP  - 3250
EP  - 3263
DO  - 10.1039/c8cp07875k
ER  - 

@article{
author = "Baranac-Stojanović, Marija and Stojanović, Milovan",
year = "2019",
abstract = "The effect of two types of dibenzo-fusion of pentalene in the singlet and triplet states on its molecular energies and magnetically induced ring currents was examined via density functional calculations. The isomerization energy decomposition analysis (IEDA) together with the calculated aromaticity indices (NICS(1) zz , HOMA and FLU π ), estimation of resonance energies (RE) and extra cyclic resonance energies (ECRE) via the NBO method, and the NICS-XY-scans revealed that the π-electronic system is the most important factor controlling the molecular energies. The [a,f] topology features greater delocalization, which results in two opposing effects: larger ECRE, but weaker π-bonding. The latter is mainly responsible for the higher energy of [a,f]-dibenzopentalene (DBP) (ΔE iso = 21.7 kcal mol -1 ), with the other effects being σ-orbital and electrostatic interactions. The reversal of energetic stability in the triplet states (ΔE iso = -10.8 kcal mol -1 ) mainly comes from the reduced Pauli repulsion in [a,f]-DBP, which stabilizes the unpaired spin density over the central trimethylenemethane subunit vs. the central pentalene subunit in [a,e]-DBP. Although the [a,e] topology only reduces the diatropic and paratropic currents of the elementary subunits, benzene and pentalene, the [a,f] topology also creates strong global paratropicity involving the benzene rings. Both DBP isomers are characterized by global and smaller semi-global and local diatropic currents in the triplet state.",
publisher = "Royal Society of Chemistry",
journal = "Physical Chemistry Chemical Physics",
title = "The effect of two types of dibenzoannulation of pentalene on molecular energies and magnetically induced currents",
volume = "21",
number = "6",
pages = "3250-3263",
doi = "10.1039/c8cp07875k"
}

Baranac-Stojanović, M.,& Stojanović, M.. (2019). The effect of two types of dibenzoannulation of pentalene on molecular energies and magnetically induced currents. in Physical Chemistry Chemical Physics
Royal Society of Chemistry., 21(6), 3250-3263.
https://doi.org/10.1039/c8cp07875k

Baranac-Stojanović M, Stojanović M. The effect of two types of dibenzoannulation of pentalene on molecular energies and magnetically induced currents. in Physical Chemistry Chemical Physics. 2019;21(6):3250-3263.
doi:10.1039/c8cp07875k .

Baranac-Stojanović, Marija, Stojanović, Milovan, "The effect of two types of dibenzoannulation of pentalene on molecular energies and magnetically induced currents" in Physical Chemistry Chemical Physics, 21, no. 6 (2019):3250-3263,
https://doi.org/10.1039/c8cp07875k . .

TY  - JOUR
AU  - Baranac-Stojanović, Marija
AU  - Stojanović, Milovan
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2961
AB  - The effect of two types of dibenzo-fusion of pentalene in the singlet and triplet states on its molecular energies and magnetically induced ring currents was examined via density functional calculations. The isomerization energy decomposition analysis (IEDA) together with the calculated aromaticity indices (NICS(1) zz , HOMA and FLU π ), estimation of resonance energies (RE) and extra cyclic resonance energies (ECRE) via the NBO method, and the NICS-XY-scans revealed that the π-electronic system is the most important factor controlling the molecular energies. The [a,f] topology features greater delocalization, which results in two opposing effects: larger ECRE, but weaker π-bonding. The latter is mainly responsible for the higher energy of [a,f]-dibenzopentalene (DBP) (ΔE iso = 21.7 kcal mol -1 ), with the other effects being σ-orbital and electrostatic interactions. The reversal of energetic stability in the triplet states (ΔE iso = -10.8 kcal mol -1 ) mainly comes from the reduced Pauli repulsion in [a,f]-DBP, which stabilizes the unpaired spin density over the central trimethylenemethane subunit vs. the central pentalene subunit in [a,e]-DBP. Although the [a,e] topology only reduces the diatropic and paratropic currents of the elementary subunits, benzene and pentalene, the [a,f] topology also creates strong global paratropicity involving the benzene rings. Both DBP isomers are characterized by global and smaller semi-global and local diatropic currents in the triplet state.
PB  - Royal Society of Chemistry
T2  - Physical Chemistry Chemical Physics
T1  - The effect of two types of dibenzoannulation of pentalene on molecular energies and magnetically induced currents
VL  - 21
IS  - 6
SP  - 3250
EP  - 3263
DO  - 10.1039/c8cp07875k
ER  - 

@article{
author = "Baranac-Stojanović, Marija and Stojanović, Milovan",
year = "2019",
abstract = "The effect of two types of dibenzo-fusion of pentalene in the singlet and triplet states on its molecular energies and magnetically induced ring currents was examined via density functional calculations. The isomerization energy decomposition analysis (IEDA) together with the calculated aromaticity indices (NICS(1) zz , HOMA and FLU π ), estimation of resonance energies (RE) and extra cyclic resonance energies (ECRE) via the NBO method, and the NICS-XY-scans revealed that the π-electronic system is the most important factor controlling the molecular energies. The [a,f] topology features greater delocalization, which results in two opposing effects: larger ECRE, but weaker π-bonding. The latter is mainly responsible for the higher energy of [a,f]-dibenzopentalene (DBP) (ΔE iso = 21.7 kcal mol -1 ), with the other effects being σ-orbital and electrostatic interactions. The reversal of energetic stability in the triplet states (ΔE iso = -10.8 kcal mol -1 ) mainly comes from the reduced Pauli repulsion in [a,f]-DBP, which stabilizes the unpaired spin density over the central trimethylenemethane subunit vs. the central pentalene subunit in [a,e]-DBP. Although the [a,e] topology only reduces the diatropic and paratropic currents of the elementary subunits, benzene and pentalene, the [a,f] topology also creates strong global paratropicity involving the benzene rings. Both DBP isomers are characterized by global and smaller semi-global and local diatropic currents in the triplet state.",
publisher = "Royal Society of Chemistry",
journal = "Physical Chemistry Chemical Physics",
title = "The effect of two types of dibenzoannulation of pentalene on molecular energies and magnetically induced currents",
volume = "21",
number = "6",
pages = "3250-3263",
doi = "10.1039/c8cp07875k"
}

Baranac-Stojanović, M.,& Stojanović, M.. (2019). The effect of two types of dibenzoannulation of pentalene on molecular energies and magnetically induced currents. in Physical Chemistry Chemical Physics
Royal Society of Chemistry., 21(6), 3250-3263.
https://doi.org/10.1039/c8cp07875k

Baranac-Stojanović M, Stojanović M. The effect of two types of dibenzoannulation of pentalene on molecular energies and magnetically induced currents. in Physical Chemistry Chemical Physics. 2019;21(6):3250-3263.
doi:10.1039/c8cp07875k .

Baranac-Stojanović, Marija, Stojanović, Milovan, "The effect of two types of dibenzoannulation of pentalene on molecular energies and magnetically induced currents" in Physical Chemistry Chemical Physics, 21, no. 6 (2019):3250-3263,
https://doi.org/10.1039/c8cp07875k . .

TY  - JOUR
AU  - Džambaski, Zdravko
AU  - Tzaras, Dimitrios‐Ioannis
AU  - Lee, Sunggi
AU  - Kokotos, Christoforos G.
AU  - Bondžić, Bojan
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2953
AB  - α,β‐unsaturated aldehydes have been traditionally used in LUMO lowering asymmetric aminocatalysis (iminium catalysis), while the use of saturated aldehydes as substrates in this type of catalysis has been elusive, until recently. Herein, we demonstrate that organic, single‐electron oxidants in the presence of diarylprolinol silylether type catalysts serve as effective tools for the transformation of electron rich enamines to iminium ions which partake in a subsequent Diels‐Alder reaction. This enantioselective one‐pot transformation represents the first example of saturated aldehydes being used in domino Diels‐Alder reaction processes and demonstrates the power of this protocol for construction of stereo‐defined chiral compounds and building blocks.
PB  - Wiley
T2  - Advanced Synthesis & Catalysis
T1  - Enantioselective Organocatalytic Enamine C−H Oxidation/Diels‐ Alder Reaction
VL  - 361
IS  - 8
SP  - 1792
EP  - 1797
DO  - 10.1002/adsc.201900061
ER  - 

@article{
author = "Džambaski, Zdravko and Tzaras, Dimitrios‐Ioannis and Lee, Sunggi and Kokotos, Christoforos G. and Bondžić, Bojan",
year = "2019",
abstract = "α,β‐unsaturated aldehydes have been traditionally used in LUMO lowering asymmetric aminocatalysis (iminium catalysis), while the use of saturated aldehydes as substrates in this type of catalysis has been elusive, until recently. Herein, we demonstrate that organic, single‐electron oxidants in the presence of diarylprolinol silylether type catalysts serve as effective tools for the transformation of electron rich enamines to iminium ions which partake in a subsequent Diels‐Alder reaction. This enantioselective one‐pot transformation represents the first example of saturated aldehydes being used in domino Diels‐Alder reaction processes and demonstrates the power of this protocol for construction of stereo‐defined chiral compounds and building blocks.",
publisher = "Wiley",
journal = "Advanced Synthesis & Catalysis",
title = "Enantioselective Organocatalytic Enamine C−H Oxidation/Diels‐ Alder Reaction",
volume = "361",
number = "8",
pages = "1792-1797",
doi = "10.1002/adsc.201900061"
}

Džambaski, Z., Tzaras, D., Lee, S., Kokotos, C. G.,& Bondžić, B.. (2019). Enantioselective Organocatalytic Enamine C−H Oxidation/Diels‐ Alder Reaction. in Advanced Synthesis & Catalysis
Wiley., 361(8), 1792-1797.
https://doi.org/10.1002/adsc.201900061

Džambaski Z, Tzaras D, Lee S, Kokotos CG, Bondžić B. Enantioselective Organocatalytic Enamine C−H Oxidation/Diels‐ Alder Reaction. in Advanced Synthesis & Catalysis. 2019;361(8):1792-1797.
doi:10.1002/adsc.201900061 .

Džambaski, Zdravko, Tzaras, Dimitrios‐Ioannis, Lee, Sunggi, Kokotos, Christoforos G., Bondžić, Bojan, "Enantioselective Organocatalytic Enamine C−H Oxidation/Diels‐ Alder Reaction" in Advanced Synthesis & Catalysis, 361, no. 8 (2019):1792-1797,
https://doi.org/10.1002/adsc.201900061 . .

TY  - JOUR
AU  - Džambaski, Zdravko
AU  - Tzaras, Dimitrios‐Ioannis
AU  - Lee, Sunggi
AU  - Kokotos, Christoforos G.
AU  - Bondžić, Bojan
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2954
AB  - α,β‐unsaturated aldehydes have been traditionally used in LUMO lowering asymmetric aminocatalysis (iminium catalysis), while the use of saturated aldehydes as substrates in this type of catalysis has been elusive, until recently. Herein, we demonstrate that organic, single‐electron oxidants in the presence of diarylprolinol silylether type catalysts serve as effective tools for the transformation of electron rich enamines to iminium ions which partake in a subsequent Diels‐Alder reaction. This enantioselective one‐pot transformation represents the first example of saturated aldehydes being used in domino Diels‐Alder reaction processes and demonstrates the power of this protocol for construction of stereo‐defined chiral compounds and building blocks.
PB  - Wiley
T2  - Advanced Synthesis & Catalysis
T1  - Enantioselective Organocatalytic Enamine C−H Oxidation/Diels‐ Alder Reaction
VL  - 361
IS  - 8
SP  - 1792
EP  - 1797
DO  - 10.1002/adsc.201900061
ER  - 

@article{
author = "Džambaski, Zdravko and Tzaras, Dimitrios‐Ioannis and Lee, Sunggi and Kokotos, Christoforos G. and Bondžić, Bojan",
year = "2019",
abstract = "α,β‐unsaturated aldehydes have been traditionally used in LUMO lowering asymmetric aminocatalysis (iminium catalysis), while the use of saturated aldehydes as substrates in this type of catalysis has been elusive, until recently. Herein, we demonstrate that organic, single‐electron oxidants in the presence of diarylprolinol silylether type catalysts serve as effective tools for the transformation of electron rich enamines to iminium ions which partake in a subsequent Diels‐Alder reaction. This enantioselective one‐pot transformation represents the first example of saturated aldehydes being used in domino Diels‐Alder reaction processes and demonstrates the power of this protocol for construction of stereo‐defined chiral compounds and building blocks.",
publisher = "Wiley",
journal = "Advanced Synthesis & Catalysis",
title = "Enantioselective Organocatalytic Enamine C−H Oxidation/Diels‐ Alder Reaction",
volume = "361",
number = "8",
pages = "1792-1797",
doi = "10.1002/adsc.201900061"
}

Džambaski, Z., Tzaras, D., Lee, S., Kokotos, C. G.,& Bondžić, B.. (2019). Enantioselective Organocatalytic Enamine C−H Oxidation/Diels‐ Alder Reaction. in Advanced Synthesis & Catalysis
Wiley., 361(8), 1792-1797.
https://doi.org/10.1002/adsc.201900061

Džambaski Z, Tzaras D, Lee S, Kokotos CG, Bondžić B. Enantioselective Organocatalytic Enamine C−H Oxidation/Diels‐ Alder Reaction. in Advanced Synthesis & Catalysis. 2019;361(8):1792-1797.
doi:10.1002/adsc.201900061 .

Džambaski, Zdravko, Tzaras, Dimitrios‐Ioannis, Lee, Sunggi, Kokotos, Christoforos G., Bondžić, Bojan, "Enantioselective Organocatalytic Enamine C−H Oxidation/Diels‐ Alder Reaction" in Advanced Synthesis & Catalysis, 361, no. 8 (2019):1792-1797,
https://doi.org/10.1002/adsc.201900061 . .

TY  - JOUR
AU  - Džambaski, Zdravko
AU  - Bondžić, Bojan
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3063
AB  - The organocatalyzed Mannich reaction of unsubstituted and N-aryl-substituted tetrahydroisoquinolines (THIQs) and the Strecker reaction of several N-aryl-substituted THIQs through dehydrogenative C(sp3)–H bond functionalization (cross-dehydrogenative coupling) promoted by organic single electron oxidants DDQ and IBX are presented. The C–H oxidation/Mannich reaction of less reactive N-aryl substituted pyrrolidines is achieved via metal catalyzed photoredox catalysis. Operationally simple procedures provide desired products in an effective and time preserving manner.
PB  - Royal Society of Chemistry (RSC)
T2  - Organic & Biomolecular Chemistry
T1  - Dehydrogenative C(sp3)–H bond functionalization of tetrahydroisoquinolines mediated by organic oxidants under mild conditions
VL  - 17
IS  - 26
SP  - 6420
EP  - 6425
DO  - 10.1039/C9OB01090D
ER  - 

@article{
author = "Džambaski, Zdravko and Bondžić, Bojan",
year = "2019",
abstract = "The organocatalyzed Mannich reaction of unsubstituted and N-aryl-substituted tetrahydroisoquinolines (THIQs) and the Strecker reaction of several N-aryl-substituted THIQs through dehydrogenative C(sp3)–H bond functionalization (cross-dehydrogenative coupling) promoted by organic single electron oxidants DDQ and IBX are presented. The C–H oxidation/Mannich reaction of less reactive N-aryl substituted pyrrolidines is achieved via metal catalyzed photoredox catalysis. Operationally simple procedures provide desired products in an effective and time preserving manner.",
publisher = "Royal Society of Chemistry (RSC)",
journal = "Organic & Biomolecular Chemistry",
title = "Dehydrogenative C(sp3)–H bond functionalization of tetrahydroisoquinolines mediated by organic oxidants under mild conditions",
volume = "17",
number = "26",
pages = "6420-6425",
doi = "10.1039/C9OB01090D"
}

Džambaski, Z.,& Bondžić, B.. (2019). Dehydrogenative C(sp3)–H bond functionalization of tetrahydroisoquinolines mediated by organic oxidants under mild conditions. in Organic & Biomolecular Chemistry
Royal Society of Chemistry (RSC)., 17(26), 6420-6425.
https://doi.org/10.1039/C9OB01090D

Džambaski Z, Bondžić B. Dehydrogenative C(sp3)–H bond functionalization of tetrahydroisoquinolines mediated by organic oxidants under mild conditions. in Organic & Biomolecular Chemistry. 2019;17(26):6420-6425.
doi:10.1039/C9OB01090D .

Džambaski, Zdravko, Bondžić, Bojan, "Dehydrogenative C(sp3)–H bond functionalization of tetrahydroisoquinolines mediated by organic oxidants under mild conditions" in Organic & Biomolecular Chemistry, 17, no. 26 (2019):6420-6425,
https://doi.org/10.1039/C9OB01090D . .

TY  - JOUR
AU  - Bondžić, Bojan
AU  - Džambaski, Zdravko
AU  - Kolarević, Ana
AU  - Đorđević, Aleksandra
AU  - Anderluh, Marko
AU  - Šmelcerović, Andrija
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3957
AB  - Eight new benzocyclobutane-2,5-diones (1a–1h) were synthesized, and their inhibitory properties
against bovine pancreatic DNase I were examined in vitro. Methods & results: Compounds 1a–1h
were synthesized using photocycloaddition of duroquinone with various phenyl-substituted ethylenes
in the presence of 18W compact fluorescent lamp (visible light). Two compounds, 1,3,4,6-tetramethyl-7-
phenylbicyclo[4.2.0]oct-3-ene-2,5-dione (1a) and 1,3,4,6-tetramethyl-7-p-tolylbicyclo[4.2.0]oct-3-ene-2,5-
dione (1b) inhibited DNase I in a noncompetitive manner with IC50 values below 150 μM and showed to
be more potent DNase I inhibitors than crystal violet, used as a positive control. In order to analyze potential
binding sites for the studied compounds with DNase I, molecular docking study was performed.
Conclusion: The studied benzocyclobutane-2,5-diones offer a good starting point for a design of new
DNase I inhibitors.
PB  - Future Medicine Ltd.
T2  - Future Medicinal Chemistry
T1  - Synthesis and DNase I inhibitory properties of new benzocyclobutane-2,5-diones
VL  - 11
VL  - 2426
IS  - 18
SP  - 2415
DO  - 10.4155/fmc-2019-0032
ER  - 

@article{
author = "Bondžić, Bojan and Džambaski, Zdravko and Kolarević, Ana and Đorđević, Aleksandra and Anderluh, Marko and Šmelcerović, Andrija",
year = "2019",
abstract = "Eight new benzocyclobutane-2,5-diones (1a–1h) were synthesized, and their inhibitory properties
against bovine pancreatic DNase I were examined in vitro. Methods & results: Compounds 1a–1h
were synthesized using photocycloaddition of duroquinone with various phenyl-substituted ethylenes
in the presence of 18W compact fluorescent lamp (visible light). Two compounds, 1,3,4,6-tetramethyl-7-
phenylbicyclo[4.2.0]oct-3-ene-2,5-dione (1a) and 1,3,4,6-tetramethyl-7-p-tolylbicyclo[4.2.0]oct-3-ene-2,5-
dione (1b) inhibited DNase I in a noncompetitive manner with IC50 values below 150 μM and showed to
be more potent DNase I inhibitors than crystal violet, used as a positive control. In order to analyze potential
binding sites for the studied compounds with DNase I, molecular docking study was performed.
Conclusion: The studied benzocyclobutane-2,5-diones offer a good starting point for a design of new
DNase I inhibitors.",
publisher = "Future Medicine Ltd.",
journal = "Future Medicinal Chemistry",
title = "Synthesis and DNase I inhibitory properties of new benzocyclobutane-2,5-diones",
volume = "11, 2426",
number = "18",
pages = "2415",
doi = "10.4155/fmc-2019-0032"
}

Bondžić, B., Džambaski, Z., Kolarević, A., Đorđević, A., Anderluh, M.,& Šmelcerović, A.. (2019). Synthesis and DNase I inhibitory properties of new benzocyclobutane-2,5-diones. in Future Medicinal Chemistry
Future Medicine Ltd.., 11(18), 2415.
https://doi.org/10.4155/fmc-2019-0032

Bondžić B, Džambaski Z, Kolarević A, Đorđević A, Anderluh M, Šmelcerović A. Synthesis and DNase I inhibitory properties of new benzocyclobutane-2,5-diones. in Future Medicinal Chemistry. 2019;11(18):2415.
doi:10.4155/fmc-2019-0032 .

Bondžić, Bojan, Džambaski, Zdravko, Kolarević, Ana, Đorđević, Aleksandra, Anderluh, Marko, Šmelcerović, Andrija, "Synthesis and DNase I inhibitory properties of new benzocyclobutane-2,5-diones" in Future Medicinal Chemistry, 11, no. 18 (2019):2415,
https://doi.org/10.4155/fmc-2019-0032 . .

TY  - JOUR
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2386
AB  - Relatively scarce literature data on BN/CC isosterism in 4nπ-electronic systems have prompted us to investigate theoretically the influence of BN pair position within the central butadiene fragment of dibenzo[a,e]pentalene on two fundamental molecular properties: stability and (anti)aromaticity. It was found that stability and aromaticity follow the same trend only for BN-orientational isomers. The source of different stability of other isomers was examined first by an analysis of bond types and their dissociation energies and then by isomerization energy decomposition analysis and was explained in terms of classical electrostatic interactions, quantum-mechanical orbital interactions, structural changes and electronic changes (transition from charge-separated π-system to the neutral one). (Anti)aromaticity was investigated by using three kinds of indices, HOMA, FLUπ, and NICS(1)zz, which indicated that delocalization at the central pentalene motif is almost unaffected by various BN arrangements, molecular perimeter is slightly affected, while the most affected subunits are five-membered rings and benzene-fused five-membered rings containing only one heteroatom.
PB  - Wiley-VCH Verlag
T2  - European Journal of Organic Chemistry
T1  - Analysis of Stability and (Anti)aromaticity of BN-Dibenzo[a,e]pentalenes
VL  - 2018
IS  - 45
SP  - 6230
EP  - 6240
DO  - 10.1002/ejoc.201801047
ER  - 

@article{
author = "Stojanović, Milovan and Baranac-Stojanović, Marija",
year = "2018",
abstract = "Relatively scarce literature data on BN/CC isosterism in 4nπ-electronic systems have prompted us to investigate theoretically the influence of BN pair position within the central butadiene fragment of dibenzo[a,e]pentalene on two fundamental molecular properties: stability and (anti)aromaticity. It was found that stability and aromaticity follow the same trend only for BN-orientational isomers. The source of different stability of other isomers was examined first by an analysis of bond types and their dissociation energies and then by isomerization energy decomposition analysis and was explained in terms of classical electrostatic interactions, quantum-mechanical orbital interactions, structural changes and electronic changes (transition from charge-separated π-system to the neutral one). (Anti)aromaticity was investigated by using three kinds of indices, HOMA, FLUπ, and NICS(1)zz, which indicated that delocalization at the central pentalene motif is almost unaffected by various BN arrangements, molecular perimeter is slightly affected, while the most affected subunits are five-membered rings and benzene-fused five-membered rings containing only one heteroatom.",
publisher = "Wiley-VCH Verlag",
journal = "European Journal of Organic Chemistry",
title = "Analysis of Stability and (Anti)aromaticity of BN-Dibenzo[a,e]pentalenes",
volume = "2018",
number = "45",
pages = "6230-6240",
doi = "10.1002/ejoc.201801047"
}

Stojanović, M.,& Baranac-Stojanović, M.. (2018). Analysis of Stability and (Anti)aromaticity of BN-Dibenzo[a,e]pentalenes. in European Journal of Organic Chemistry
Wiley-VCH Verlag., 2018(45), 6230-6240.
https://doi.org/10.1002/ejoc.201801047

Stojanović M, Baranac-Stojanović M. Analysis of Stability and (Anti)aromaticity of BN-Dibenzo[a,e]pentalenes. in European Journal of Organic Chemistry. 2018;2018(45):6230-6240.
doi:10.1002/ejoc.201801047 .

Stojanović, Milovan, Baranac-Stojanović, Marija, "Analysis of Stability and (Anti)aromaticity of BN-Dibenzo[a,e]pentalenes" in European Journal of Organic Chemistry, 2018, no. 45 (2018):6230-6240,
https://doi.org/10.1002/ejoc.201801047 . .

TY  - JOUR
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2432
AB  - All isomeric BN isosteres of naphthalene have been studied theoretically, at the B3LYP/6-311+G(d,p) level, in order to investigate the effect of the BN position in a molecule on relative stability, aromaticity and frontier orbital energies. The results show that the orientational isomers of m,n/n,m type have similar aromaticity, similar HOMO-LUMO gaps and similar stability, though the latter only when both heteroatoms occupy external ring positions. This latter finding is explained by an analysis of partial atomic charges in the parent hydrocarbon and final BN-compound. Racing the BN pair in one ring results in larger stability and larger HOMO-LUMO gaps than when it is placed in separate rings. The stability order of the former series is predictable on the basis of charge distribution in the nitrogen-polarized naphthalenic system and is related to partial atomic charges at the boron and nitrogen atoms in a BN-heterocycle. The HOMO-LUMO gap of the parental hydrocarbon is retained only in the 1,4-isomer, it is slightly increased in 1,2/2,1 and 5,10 isomers and more or less decreased in all other isomers. The aromaticity of a benzene unit in naphthalene is retained/increased only in a carbocycle, when it can be represented as having a pi-electronic sextet. The aromaticity of heterocyclic rings is more or less reduced relative to naphthalene and is the weakest in the rings featuring the push-pull pi-electronic structure while the BN pair resides at the external ring positions.
PB  - Royal Soc Chemistry, Cambridge
T2  - New Journal of Chemistry
T1  - Mono BN-substituted analogues of naphthalene: a theoretical analysis of the effect of BN position on stability, aromaticity and frontier orbital energies
VL  - 42
IS  - 15
SP  - 12968
EP  - 12976
DO  - 10.1039/c8nj01529e
ER  - 

@article{
author = "Stojanović, Milovan and Baranac-Stojanović, Marija",
year = "2018",
abstract = "All isomeric BN isosteres of naphthalene have been studied theoretically, at the B3LYP/6-311+G(d,p) level, in order to investigate the effect of the BN position in a molecule on relative stability, aromaticity and frontier orbital energies. The results show that the orientational isomers of m,n/n,m type have similar aromaticity, similar HOMO-LUMO gaps and similar stability, though the latter only when both heteroatoms occupy external ring positions. This latter finding is explained by an analysis of partial atomic charges in the parent hydrocarbon and final BN-compound. Racing the BN pair in one ring results in larger stability and larger HOMO-LUMO gaps than when it is placed in separate rings. The stability order of the former series is predictable on the basis of charge distribution in the nitrogen-polarized naphthalenic system and is related to partial atomic charges at the boron and nitrogen atoms in a BN-heterocycle. The HOMO-LUMO gap of the parental hydrocarbon is retained only in the 1,4-isomer, it is slightly increased in 1,2/2,1 and 5,10 isomers and more or less decreased in all other isomers. The aromaticity of a benzene unit in naphthalene is retained/increased only in a carbocycle, when it can be represented as having a pi-electronic sextet. The aromaticity of heterocyclic rings is more or less reduced relative to naphthalene and is the weakest in the rings featuring the push-pull pi-electronic structure while the BN pair resides at the external ring positions.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "New Journal of Chemistry",
title = "Mono BN-substituted analogues of naphthalene: a theoretical analysis of the effect of BN position on stability, aromaticity and frontier orbital energies",
volume = "42",
number = "15",
pages = "12968-12976",
doi = "10.1039/c8nj01529e"
}

Stojanović, M.,& Baranac-Stojanović, M.. (2018). Mono BN-substituted analogues of naphthalene: a theoretical analysis of the effect of BN position on stability, aromaticity and frontier orbital energies. in New Journal of Chemistry
Royal Soc Chemistry, Cambridge., 42(15), 12968-12976.
https://doi.org/10.1039/c8nj01529e

Stojanović M, Baranac-Stojanović M. Mono BN-substituted analogues of naphthalene: a theoretical analysis of the effect of BN position on stability, aromaticity and frontier orbital energies. in New Journal of Chemistry. 2018;42(15):12968-12976.
doi:10.1039/c8nj01529e .

Stojanović, Milovan, Baranac-Stojanović, Marija, "Mono BN-substituted analogues of naphthalene: a theoretical analysis of the effect of BN position on stability, aromaticity and frontier orbital energies" in New Journal of Chemistry, 42, no. 15 (2018):12968-12976,
https://doi.org/10.1039/c8nj01529e . .

TY  - JOUR
AU  - Aleksić, Jovana
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2451
AB  - We present an efficient, simple, metal- and solvent-free silica-gel-promoted synthesis of functionalized conjugated dienes by sequential aza-Michael/Michael reactions by starting from commercially available primary amines and propiolic esters. The scope and usefulness of the method is demonstrated for 31examples, including a range of propiolic esters, aliphatic amines, and differently substituted aromatic amines. For aliphatic amines, the products were obtained within 0.5 to 4h in 52 to 85% yield, compared with 3.5 to 22h under classical solution-phase synthesis, which proceeds with similar or lower yields. The method was found to be particularly useful for weakly nucleophilic aromatic amines, which provided products in 21 to 73% yield over 2.5 to 9.5h compared with yields of 0 to 49% over 1 to 6d under standard solution-phase conditions, and for more hydrophobic esters that gave products in yields of 47 to 79% over 1 to 3h compared with 0 to 45% over 4 to 114h in solvent.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Chemistry-An Asian Journal
T1  - Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes
VL  - 13
IS  - 14
SP  - 1811
EP  - 1835
DO  - 10.1002/asia.201800645
ER  - 

@article{
author = "Aleksić, Jovana and Stojanović, Milovan and Baranac-Stojanović, Marija",
year = "2018",
abstract = "We present an efficient, simple, metal- and solvent-free silica-gel-promoted synthesis of functionalized conjugated dienes by sequential aza-Michael/Michael reactions by starting from commercially available primary amines and propiolic esters. The scope and usefulness of the method is demonstrated for 31examples, including a range of propiolic esters, aliphatic amines, and differently substituted aromatic amines. For aliphatic amines, the products were obtained within 0.5 to 4h in 52 to 85% yield, compared with 3.5 to 22h under classical solution-phase synthesis, which proceeds with similar or lower yields. The method was found to be particularly useful for weakly nucleophilic aromatic amines, which provided products in 21 to 73% yield over 2.5 to 9.5h compared with yields of 0 to 49% over 1 to 6d under standard solution-phase conditions, and for more hydrophobic esters that gave products in yields of 47 to 79% over 1 to 3h compared with 0 to 45% over 4 to 114h in solvent.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Chemistry-An Asian Journal",
title = "Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes",
volume = "13",
number = "14",
pages = "1811-1835",
doi = "10.1002/asia.201800645"
}

Aleksić, J., Stojanović, M.,& Baranac-Stojanović, M.. (2018). Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes. in Chemistry-An Asian Journal
Wiley-V C H Verlag Gmbh, Weinheim., 13(14), 1811-1835.
https://doi.org/10.1002/asia.201800645

Aleksić J, Stojanović M, Baranac-Stojanović M. Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes. in Chemistry-An Asian Journal. 2018;13(14):1811-1835.
doi:10.1002/asia.201800645 .

Aleksić, Jovana, Stojanović, Milovan, Baranac-Stojanović, Marija, "Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes" in Chemistry-An Asian Journal, 13, no. 14 (2018):1811-1835,
https://doi.org/10.1002/asia.201800645 . .

TY  - JOUR
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2970
AB  - All isomeric BN isosteres of naphthalene have been studied theoretically, at the B3LYP/6-311+G(d,p) level, in order to investigate the effect of the BN position in a molecule on relative stability, aromaticity and frontier orbital energies. The results show that the orientational isomers of m,n/n,m type have similar aromaticity, similar HOMO-LUMO gaps and similar stability, though the latter only when both heteroatoms occupy external ring positions. This latter finding is explained by an analysis of partial atomic charges in the parent hydrocarbon and final BN-compound. Racing the BN pair in one ring results in larger stability and larger HOMO-LUMO gaps than when it is placed in separate rings. The stability order of the former series is predictable on the basis of charge distribution in the nitrogen-polarized naphthalenic system and is related to partial atomic charges at the boron and nitrogen atoms in a BN-heterocycle. The HOMO-LUMO gap of the parental hydrocarbon is retained only in the 1,4-isomer, it is slightly increased in 1,2/2,1 and 5,10 isomers and more or less decreased in all other isomers. The aromaticity of a benzene unit in naphthalene is retained/increased only in a carbocycle, when it can be represented as having a pi-electronic sextet. The aromaticity of heterocyclic rings is more or less reduced relative to naphthalene and is the weakest in the rings featuring the push-pull pi-electronic structure while the BN pair resides at the external ring positions.
PB  - Royal Soc Chemistry, Cambridge
T2  - New Journal of Chemistry
T1  - Mono BN-substituted analogues of naphthalene: a theoretical analysis of the effect of BN position on stability, aromaticity and frontier orbital energies
VL  - 42
IS  - 15
SP  - 12968
EP  - 12976
DO  - 10.1039/c8nj01529e
ER  - 

@article{
author = "Stojanović, Milovan and Baranac-Stojanović, Marija",
year = "2018",
abstract = "All isomeric BN isosteres of naphthalene have been studied theoretically, at the B3LYP/6-311+G(d,p) level, in order to investigate the effect of the BN position in a molecule on relative stability, aromaticity and frontier orbital energies. The results show that the orientational isomers of m,n/n,m type have similar aromaticity, similar HOMO-LUMO gaps and similar stability, though the latter only when both heteroatoms occupy external ring positions. This latter finding is explained by an analysis of partial atomic charges in the parent hydrocarbon and final BN-compound. Racing the BN pair in one ring results in larger stability and larger HOMO-LUMO gaps than when it is placed in separate rings. The stability order of the former series is predictable on the basis of charge distribution in the nitrogen-polarized naphthalenic system and is related to partial atomic charges at the boron and nitrogen atoms in a BN-heterocycle. The HOMO-LUMO gap of the parental hydrocarbon is retained only in the 1,4-isomer, it is slightly increased in 1,2/2,1 and 5,10 isomers and more or less decreased in all other isomers. The aromaticity of a benzene unit in naphthalene is retained/increased only in a carbocycle, when it can be represented as having a pi-electronic sextet. The aromaticity of heterocyclic rings is more or less reduced relative to naphthalene and is the weakest in the rings featuring the push-pull pi-electronic structure while the BN pair resides at the external ring positions.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "New Journal of Chemistry",
title = "Mono BN-substituted analogues of naphthalene: a theoretical analysis of the effect of BN position on stability, aromaticity and frontier orbital energies",
volume = "42",
number = "15",
pages = "12968-12976",
doi = "10.1039/c8nj01529e"
}

Stojanović, M.,& Baranac-Stojanović, M.. (2018). Mono BN-substituted analogues of naphthalene: a theoretical analysis of the effect of BN position on stability, aromaticity and frontier orbital energies. in New Journal of Chemistry
Royal Soc Chemistry, Cambridge., 42(15), 12968-12976.
https://doi.org/10.1039/c8nj01529e

Stojanović M, Baranac-Stojanović M. Mono BN-substituted analogues of naphthalene: a theoretical analysis of the effect of BN position on stability, aromaticity and frontier orbital energies. in New Journal of Chemistry. 2018;42(15):12968-12976.
doi:10.1039/c8nj01529e .

Stojanović, Milovan, Baranac-Stojanović, Marija, "Mono BN-substituted analogues of naphthalene: a theoretical analysis of the effect of BN position on stability, aromaticity and frontier orbital energies" in New Journal of Chemistry, 42, no. 15 (2018):12968-12976,
https://doi.org/10.1039/c8nj01529e . .

TY  - JOUR
AU  - Aleksić, Jovana
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3135
AB  - We present an efficient, simple, metal- and solvent-free silica-gel-promoted synthesis of functionalized conjugated dienes by sequential aza-Michael/Michael reactions by starting from commercially available primary amines and propiolic esters. The scope and usefulness of the method is demonstrated for 31examples, including a range of propiolic esters, aliphatic amines, and differently substituted aromatic amines. For aliphatic amines, the products were obtained within 0.5 to 4h in 52 to 85% yield, compared with 3.5 to 22h under classical solution-phase synthesis, which proceeds with similar or lower yields. The method was found to be particularly useful for weakly nucleophilic aromatic amines, which provided products in 21 to 73% yield over 2.5 to 9.5h compared with yields of 0 to 49% over 1 to 6d under standard solution-phase conditions, and for more hydrophobic esters that gave products in yields of 47 to 79% over 1 to 3h compared with 0 to 45% over 4 to 114h in solvent.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Chemistry-An Asian Journal
T1  - Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes
VL  - 13
IS  - 14
SP  - 1811
EP  - 1835
DO  - 10.1002/asia.201800645
ER  - 

@article{
author = "Aleksić, Jovana and Stojanović, Milovan and Baranac-Stojanović, Marija",
year = "2018",
abstract = "We present an efficient, simple, metal- and solvent-free silica-gel-promoted synthesis of functionalized conjugated dienes by sequential aza-Michael/Michael reactions by starting from commercially available primary amines and propiolic esters. The scope and usefulness of the method is demonstrated for 31examples, including a range of propiolic esters, aliphatic amines, and differently substituted aromatic amines. For aliphatic amines, the products were obtained within 0.5 to 4h in 52 to 85% yield, compared with 3.5 to 22h under classical solution-phase synthesis, which proceeds with similar or lower yields. The method was found to be particularly useful for weakly nucleophilic aromatic amines, which provided products in 21 to 73% yield over 2.5 to 9.5h compared with yields of 0 to 49% over 1 to 6d under standard solution-phase conditions, and for more hydrophobic esters that gave products in yields of 47 to 79% over 1 to 3h compared with 0 to 45% over 4 to 114h in solvent.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Chemistry-An Asian Journal",
title = "Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes",
volume = "13",
number = "14",
pages = "1811-1835",
doi = "10.1002/asia.201800645"
}

Aleksić, J., Stojanović, M.,& Baranac-Stojanović, M.. (2018). Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes. in Chemistry-An Asian Journal
Wiley-V C H Verlag Gmbh, Weinheim., 13(14), 1811-1835.
https://doi.org/10.1002/asia.201800645

Aleksić J, Stojanović M, Baranac-Stojanović M. Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes. in Chemistry-An Asian Journal. 2018;13(14):1811-1835.
doi:10.1002/asia.201800645 .

Aleksić, Jovana, Stojanović, Milovan, Baranac-Stojanović, Marija, "Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes" in Chemistry-An Asian Journal, 13, no. 14 (2018):1811-1835,
https://doi.org/10.1002/asia.201800645 . .

TY  - DATA
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4477
AB  - Table S1. Experimental and calculated bond lengths and bond angles for 1,4 isomer of BN-dibenzopentalene; Table S2. Spin densities in diradical state of 1,3 isomer of BN-dibenzopentalene obtained by Hirshfeld population analysis; Figure S1. Relative energies of six isomeric BN-dibenzopentalenes, BN-butadienes and BN-pentalenes; Figure S2. NICS-XY scans. Section S1: Comparison of (anti)aromaticity of various isomers of BN-dibenzopentalenes. Absolute energies and X, Y, Z coordinates of optimized structures.
PB  - Wiley
T2  - European Journal of Organic Chemistry
T1  - Supporting information for: "Analysis of Stability and (Anti)aromaticity of BN-Dibenzo[a,e]pentalenes"
UR  - https://hdl.handle.net/21.15107/rcub_cer_4477
ER  - 

@misc{
author = "Stojanović, Milovan and Baranac-Stojanović, Marija",
year = "2018",
abstract = "Table S1. Experimental and calculated bond lengths and bond angles for 1,4 isomer of BN-dibenzopentalene; Table S2. Spin densities in diradical state of 1,3 isomer of BN-dibenzopentalene obtained by Hirshfeld population analysis; Figure S1. Relative energies of six isomeric BN-dibenzopentalenes, BN-butadienes and BN-pentalenes; Figure S2. NICS-XY scans. Section S1: Comparison of (anti)aromaticity of various isomers of BN-dibenzopentalenes. Absolute energies and X, Y, Z coordinates of optimized structures.",
publisher = "Wiley",
journal = "European Journal of Organic Chemistry",
title = "Supporting information for: "Analysis of Stability and (Anti)aromaticity of BN-Dibenzo[a,e]pentalenes"",
url = "https://hdl.handle.net/21.15107/rcub_cer_4477"
}

Stojanović, M.,& Baranac-Stojanović, M.. (2018). Supporting information for: "Analysis of Stability and (Anti)aromaticity of BN-Dibenzo[a,e]pentalenes". in European Journal of Organic Chemistry
Wiley..
https://hdl.handle.net/21.15107/rcub_cer_4477

Stojanović M, Baranac-Stojanović M. Supporting information for: "Analysis of Stability and (Anti)aromaticity of BN-Dibenzo[a,e]pentalenes". in European Journal of Organic Chemistry. 2018;.
https://hdl.handle.net/21.15107/rcub_cer_4477 .

Stojanović, Milovan, Baranac-Stojanović, Marija, "Supporting information for: "Analysis of Stability and (Anti)aromaticity of BN-Dibenzo[a,e]pentalenes"" in European Journal of Organic Chemistry (2018),
https://hdl.handle.net/21.15107/rcub_cer_4477 .

TY  - DATA
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4491
AB  - All isomeric BN isosteres of naphthalene have been studied theoretically, at the B3LYP/6-311+G(d,p) level, in order to investigate the effect of the BN position in a molecule on relative stability, aromaticity and frontier orbital energies. The results show that the orientational isomers of m,n/n,m type have similar aromaticity, similar HOMO-LUMO gaps and similar stability, though the latter only when both heteroatoms occupy external ring positions. This latter finding is explained by an analysis of partial atomic charges in the parent hydrocarbon and final BN-compound. Racing the BN pair in one ring results in larger stability and larger HOMO-LUMO gaps than when it is placed in separate rings. The stability order of the former series is predictable on the basis of charge distribution in the nitrogen-polarized naphthalenic system and is related to partial atomic charges at the boron and nitrogen atoms in a BN-heterocycle. The HOMO-LUMO gap of the parental hydrocarbon is retained only in the 1,4-isomer, it is slightly increased in 1,2/2,1 and 5,10 isomers and more or less decreased in all other isomers. The aromaticity of a benzene unit in naphthalene is retained/increased only in a carbocycle, when it can be represented as having a pi-electronic sextet. The aromaticity of heterocyclic rings is more or less reduced relative to naphthalene and is the weakest in the rings featuring the push-pull pi-electronic structure while the BN pair resides at the external ring positions.
PB  - Royal Society for Chemistry
T2  - New Journal of Chemistry
T1  - Supplementary Material for: "Mono BN-substituted analogues of naphthalene: a theoretical analysis of the effect of BN position on stability, aromaticity and frontier orbital energies"
DO  - 10.1039/c8nj01529e
ER  - 

@misc{
author = "Stojanović, Milovan and Baranac-Stojanović, Marija",
year = "2018",
abstract = "All isomeric BN isosteres of naphthalene have been studied theoretically, at the B3LYP/6-311+G(d,p) level, in order to investigate the effect of the BN position in a molecule on relative stability, aromaticity and frontier orbital energies. The results show that the orientational isomers of m,n/n,m type have similar aromaticity, similar HOMO-LUMO gaps and similar stability, though the latter only when both heteroatoms occupy external ring positions. This latter finding is explained by an analysis of partial atomic charges in the parent hydrocarbon and final BN-compound. Racing the BN pair in one ring results in larger stability and larger HOMO-LUMO gaps than when it is placed in separate rings. The stability order of the former series is predictable on the basis of charge distribution in the nitrogen-polarized naphthalenic system and is related to partial atomic charges at the boron and nitrogen atoms in a BN-heterocycle. The HOMO-LUMO gap of the parental hydrocarbon is retained only in the 1,4-isomer, it is slightly increased in 1,2/2,1 and 5,10 isomers and more or less decreased in all other isomers. The aromaticity of a benzene unit in naphthalene is retained/increased only in a carbocycle, when it can be represented as having a pi-electronic sextet. The aromaticity of heterocyclic rings is more or less reduced relative to naphthalene and is the weakest in the rings featuring the push-pull pi-electronic structure while the BN pair resides at the external ring positions.",
publisher = "Royal Society for Chemistry",
journal = "New Journal of Chemistry",
title = "Supplementary Material for: "Mono BN-substituted analogues of naphthalene: a theoretical analysis of the effect of BN position on stability, aromaticity and frontier orbital energies"",
doi = "10.1039/c8nj01529e"
}

Stojanović, M.,& Baranac-Stojanović, M.. (2018). Supplementary Material for: "Mono BN-substituted analogues of naphthalene: a theoretical analysis of the effect of BN position on stability, aromaticity and frontier orbital energies". in New Journal of Chemistry
Royal Society for Chemistry..
https://doi.org/10.1039/c8nj01529e

Stojanović M, Baranac-Stojanović M. Supplementary Material for: "Mono BN-substituted analogues of naphthalene: a theoretical analysis of the effect of BN position on stability, aromaticity and frontier orbital energies". in New Journal of Chemistry. 2018;.
doi:10.1039/c8nj01529e .

Stojanović, Milovan, Baranac-Stojanović, Marija, "Supplementary Material for: "Mono BN-substituted analogues of naphthalene: a theoretical analysis of the effect of BN position on stability, aromaticity and frontier orbital energies"" in New Journal of Chemistry (2018),
https://doi.org/10.1039/c8nj01529e . .

TY  - JOUR
AU  - Kolarević, Ana
AU  - Ilić, Budimir S.
AU  - Kocić, Gordana
AU  - Džambaski, Zdravko
AU  - Šmelcerović, Andrija
AU  - Bondžić, Bojan
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2998
AB  - Twelve new thiazolidinones were synthesized and, together with 41 previously
synthesized thiazolidinones, evaluated for inhibitory activity against deoxyribonuclease I (DNase I) in vitro. Ten compounds inhibited commercial bovine pancreatic DNase I with an IC50 below 200 μM and showed to be more potent DNase I inhibitors than crystal violet (IC50 = 365.90 ± 47.33 μM), used as a positive control. Moreover, three compounds were active against DNase I in rat
liver homogenate, having an IC50 below 200 μM. (3‐Methyl‐1,4‐dioxothiazolidin‐2‐ylidene)‐N‐(2‐phenylethyl)ethanamide (41) exhibited the most potent DNase I inhibition against both commercial and rat liver DNase I with IC50 values of 115.96 ± 11.70 and 151.36 ± 15.85 μM, respectively. Site Finder and molecular docking defined the thiazolidinones interactions with the most important catalytic residues of DNase I, including the H‐acceptor interaction with residues His 134 and His 252 and/or H‐donor interaction with residues Glu 39 and Asp 168. The three most active compounds against both commercial and rat liver DNase I (31, 38, and 41) exhibited favorable physico‐chemical, pharmacokinetic, and toxicological properties. These observations could be
utilized to guide the rational design and optimization of novel thiazolidinone inhibitors. Thiazolidinones as novel DNase I inhibitors could have potential therapeutic applications due to the significant involvement of DNase I in the pathophysiology of many disease conditions.
PB  - Wiley
T2  - Journal of Cellular Biochemistry
T1  - Synthesis and DNase I inhibitory properties of some 4‐thiazolidinone derivatives
VL  - 120
IS  - 1
SP  - 264
EP  - 274
DO  - 10.1002/jcb.27339
ER  - 

@article{
author = "Kolarević, Ana and Ilić, Budimir S. and Kocić, Gordana and Džambaski, Zdravko and Šmelcerović, Andrija and Bondžić, Bojan",
year = "2018",
abstract = "Twelve new thiazolidinones were synthesized and, together with 41 previously
synthesized thiazolidinones, evaluated for inhibitory activity against deoxyribonuclease I (DNase I) in vitro. Ten compounds inhibited commercial bovine pancreatic DNase I with an IC50 below 200 μM and showed to be more potent DNase I inhibitors than crystal violet (IC50 = 365.90 ± 47.33 μM), used as a positive control. Moreover, three compounds were active against DNase I in rat
liver homogenate, having an IC50 below 200 μM. (3‐Methyl‐1,4‐dioxothiazolidin‐2‐ylidene)‐N‐(2‐phenylethyl)ethanamide (41) exhibited the most potent DNase I inhibition against both commercial and rat liver DNase I with IC50 values of 115.96 ± 11.70 and 151.36 ± 15.85 μM, respectively. Site Finder and molecular docking defined the thiazolidinones interactions with the most important catalytic residues of DNase I, including the H‐acceptor interaction with residues His 134 and His 252 and/or H‐donor interaction with residues Glu 39 and Asp 168. The three most active compounds against both commercial and rat liver DNase I (31, 38, and 41) exhibited favorable physico‐chemical, pharmacokinetic, and toxicological properties. These observations could be
utilized to guide the rational design and optimization of novel thiazolidinone inhibitors. Thiazolidinones as novel DNase I inhibitors could have potential therapeutic applications due to the significant involvement of DNase I in the pathophysiology of many disease conditions.",
publisher = "Wiley",
journal = "Journal of Cellular Biochemistry",
title = "Synthesis and DNase I inhibitory properties of some 4‐thiazolidinone derivatives",
volume = "120",
number = "1",
pages = "264-274",
doi = "10.1002/jcb.27339"
}

Kolarević, A., Ilić, B. S., Kocić, G., Džambaski, Z., Šmelcerović, A.,& Bondžić, B.. (2018). Synthesis and DNase I inhibitory properties of some 4‐thiazolidinone derivatives. in Journal of Cellular Biochemistry
Wiley., 120(1), 264-274.
https://doi.org/10.1002/jcb.27339

Kolarević A, Ilić BS, Kocić G, Džambaski Z, Šmelcerović A, Bondžić B. Synthesis and DNase I inhibitory properties of some 4‐thiazolidinone derivatives. in Journal of Cellular Biochemistry. 2018;120(1):264-274.
doi:10.1002/jcb.27339 .

Kolarević, Ana, Ilić, Budimir S., Kocić, Gordana, Džambaski, Zdravko, Šmelcerović, Andrija, Bondžić, Bojan, "Synthesis and DNase I inhibitory properties of some 4‐thiazolidinone derivatives" in Journal of Cellular Biochemistry, 120, no. 1 (2018):264-274,
https://doi.org/10.1002/jcb.27339 . .

TY  - JOUR
AU  - Džambaski, Zdravko
AU  - Baranac-Stojanović, Marija
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2190
AB  - We have studied pi electron delocalization in electron- deficient alkenes and push- pull alkenes by means of natural bond orbital analysis at the B3LYP/6-311+ G(d,p) level. The study revealed that the rarely mentioned pi electron donation from an electron-accepting group (Acc) toward the C=C double bond in push-pull alkenes and electron-deficient alkenes can provide up to 10% of total pi electron stabilizing energy of a push-pull system and as much as 45% in a strongly electron-deficient tetracyanoethene. The Acc -> C= C bond pi electron donation is more intense in s-trans than in s-cis conformational arrangement, but is less dependent on Z/E isomerism in push-pull alkenes, being slightly more pronounced in Z isomers. Among different Acc substituents, CN and COO-groups contribute the largest percent of stabilizing energy and NO2 the smallest. Increase in the number of Acc groups increases percentage contribution of Acc -> C= C bond p electron delocalization to a system stabilization. A difference in pi*(C=C) orbital occupancy between isomers can be related with their chemical reactivity.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Chemistryselect
T1  - Electron Delocalization in Electron-Deficient Alkenes and Push-Pull Alkenes
VL  - 2
IS  - 1
SP  - 42
EP  - 50
DO  - 10.1002/slct.201601661
ER  - 

@article{
author = "Džambaski, Zdravko and Baranac-Stojanović, Marija",
year = "2017",
abstract = "We have studied pi electron delocalization in electron- deficient alkenes and push- pull alkenes by means of natural bond orbital analysis at the B3LYP/6-311+ G(d,p) level. The study revealed that the rarely mentioned pi electron donation from an electron-accepting group (Acc) toward the C=C double bond in push-pull alkenes and electron-deficient alkenes can provide up to 10% of total pi electron stabilizing energy of a push-pull system and as much as 45% in a strongly electron-deficient tetracyanoethene. The Acc -> C= C bond pi electron donation is more intense in s-trans than in s-cis conformational arrangement, but is less dependent on Z/E isomerism in push-pull alkenes, being slightly more pronounced in Z isomers. Among different Acc substituents, CN and COO-groups contribute the largest percent of stabilizing energy and NO2 the smallest. Increase in the number of Acc groups increases percentage contribution of Acc -> C= C bond p electron delocalization to a system stabilization. A difference in pi*(C=C) orbital occupancy between isomers can be related with their chemical reactivity.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Chemistryselect",
title = "Electron Delocalization in Electron-Deficient Alkenes and Push-Pull Alkenes",
volume = "2",
number = "1",
pages = "42-50",
doi = "10.1002/slct.201601661"
}

Džambaski, Z.,& Baranac-Stojanović, M.. (2017). Electron Delocalization in Electron-Deficient Alkenes and Push-Pull Alkenes. in Chemistryselect
Wiley-V C H Verlag Gmbh, Weinheim., 2(1), 42-50.
https://doi.org/10.1002/slct.201601661

Džambaski Z, Baranac-Stojanović M. Electron Delocalization in Electron-Deficient Alkenes and Push-Pull Alkenes. in Chemistryselect. 2017;2(1):42-50.
doi:10.1002/slct.201601661 .

Džambaski, Zdravko, Baranac-Stojanović, Marija, "Electron Delocalization in Electron-Deficient Alkenes and Push-Pull Alkenes" in Chemistryselect, 2, no. 1 (2017):42-50,
https://doi.org/10.1002/slct.201601661 . .

TY  - JOUR
AU  - Baranac-Stojanović, Marija
AU  - Stojanović, Milovan
AU  - Aleksić, Jovana
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2264
AB  - The strength of the azido gauche effect in 1,2-diazidoethane, N-(2-azidoethyl)ethanamide, (protonated) 2-azidoethanamine and (protonated) 2-azidoethanol and its origin were theoretically studied at the MP2/6-311++G(d,p) level of theory. The results show that the azido gauche effect in the amine and alcohol can exert a control over the molecular conformation to a similar extent as the fluorine gauche effect, but to a greater extent in the charged species, amide and vicinal diazido fragment. A quantitative partitioning of isomerization energy into contributions from electrostatic, orbital, dispersion and Pauli interactions and energy consumed in structural changes revealed that electrostatic forces play an important role in the stabilization of the gauche isomer in the two charged species and alcohol. Electrostatic and dispersion interactions are the main contributors to the gauche effect in the amide, whereas dispersion and orbital interactions can be considered to be the two most important stabilizing factors of the gauche form in the vicinal diazido fragment. The interplay of all three stabilizing interactions determines the gauche preference in the amine. Stereoelectronic effects, which are involved in orbital interactions, contribute to the gauche effect in all the molecules except the 2-azidoethylammonium ion and protonated 2-azidoethanol. Hydrogen-bonding interactions were found only in the protonated alcohol.
PB  - Royal Soc Chemistry, Cambridge
T2  - New Journal of Chemistry
T1  - Theoretical study of azido gauche effect and its origin
VL  - 41
IS  - 11
SP  - 4644
EP  - 4661
DO  - 10.1039/c7nj00369b
ER  - 

@article{
author = "Baranac-Stojanović, Marija and Stojanović, Milovan and Aleksić, Jovana",
year = "2017",
abstract = "The strength of the azido gauche effect in 1,2-diazidoethane, N-(2-azidoethyl)ethanamide, (protonated) 2-azidoethanamine and (protonated) 2-azidoethanol and its origin were theoretically studied at the MP2/6-311++G(d,p) level of theory. The results show that the azido gauche effect in the amine and alcohol can exert a control over the molecular conformation to a similar extent as the fluorine gauche effect, but to a greater extent in the charged species, amide and vicinal diazido fragment. A quantitative partitioning of isomerization energy into contributions from electrostatic, orbital, dispersion and Pauli interactions and energy consumed in structural changes revealed that electrostatic forces play an important role in the stabilization of the gauche isomer in the two charged species and alcohol. Electrostatic and dispersion interactions are the main contributors to the gauche effect in the amide, whereas dispersion and orbital interactions can be considered to be the two most important stabilizing factors of the gauche form in the vicinal diazido fragment. The interplay of all three stabilizing interactions determines the gauche preference in the amine. Stereoelectronic effects, which are involved in orbital interactions, contribute to the gauche effect in all the molecules except the 2-azidoethylammonium ion and protonated 2-azidoethanol. Hydrogen-bonding interactions were found only in the protonated alcohol.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "New Journal of Chemistry",
title = "Theoretical study of azido gauche effect and its origin",
volume = "41",
number = "11",
pages = "4644-4661",
doi = "10.1039/c7nj00369b"
}

Baranac-Stojanović, M., Stojanović, M.,& Aleksić, J.. (2017). Theoretical study of azido gauche effect and its origin. in New Journal of Chemistry
Royal Soc Chemistry, Cambridge., 41(11), 4644-4661.
https://doi.org/10.1039/c7nj00369b

Baranac-Stojanović M, Stojanović M, Aleksić J. Theoretical study of azido gauche effect and its origin. in New Journal of Chemistry. 2017;41(11):4644-4661.
doi:10.1039/c7nj00369b .

Baranac-Stojanović, Marija, Stojanović, Milovan, Aleksić, Jovana, "Theoretical study of azido gauche effect and its origin" in New Journal of Chemistry, 41, no. 11 (2017):4644-4661,
https://doi.org/10.1039/c7nj00369b . .

TY  - JOUR
AU  - Baranac-Stojanović, Marija
AU  - Stojanović, Milovan
AU  - Aleksić, Jovana
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2969
AB  - The strength of the azido gauche effect in 1,2-diazidoethane, N-(2-azidoethyl)ethanamide, (protonated) 2-azidoethanamine and (protonated) 2-azidoethanol and its origin were theoretically studied at the MP2/6-311++G(d,p) level of theory. The results show that the azido gauche effect in the amine and alcohol can exert a control over the molecular conformation to a similar extent as the fluorine gauche effect, but to a greater extent in the charged species, amide and vicinal diazido fragment. A quantitative partitioning of isomerization energy into contributions from electrostatic, orbital, dispersion and Pauli interactions and energy consumed in structural changes revealed that electrostatic forces play an important role in the stabilization of the gauche isomer in the two charged species and alcohol. Electrostatic and dispersion interactions are the main contributors to the gauche effect in the amide, whereas dispersion and orbital interactions can be considered to be the two most important stabilizing factors of the gauche form in the vicinal diazido fragment. The interplay of all three stabilizing interactions determines the gauche preference in the amine. Stereoelectronic effects, which are involved in orbital interactions, contribute to the gauche effect in all the molecules except the 2-azidoethylammonium ion and protonated 2-azidoethanol. Hydrogen-bonding interactions were found only in the protonated alcohol.
PB  - Royal Soc Chemistry, Cambridge
T2  - New Journal of Chemistry
T1  - Theoretical study of azido gauche effect and its origin
VL  - 41
IS  - 11
SP  - 4644
EP  - 4661
DO  - 10.1039/c7nj00369b
ER  - 

@article{
author = "Baranac-Stojanović, Marija and Stojanović, Milovan and Aleksić, Jovana",
year = "2017",
abstract = "The strength of the azido gauche effect in 1,2-diazidoethane, N-(2-azidoethyl)ethanamide, (protonated) 2-azidoethanamine and (protonated) 2-azidoethanol and its origin were theoretically studied at the MP2/6-311++G(d,p) level of theory. The results show that the azido gauche effect in the amine and alcohol can exert a control over the molecular conformation to a similar extent as the fluorine gauche effect, but to a greater extent in the charged species, amide and vicinal diazido fragment. A quantitative partitioning of isomerization energy into contributions from electrostatic, orbital, dispersion and Pauli interactions and energy consumed in structural changes revealed that electrostatic forces play an important role in the stabilization of the gauche isomer in the two charged species and alcohol. Electrostatic and dispersion interactions are the main contributors to the gauche effect in the amide, whereas dispersion and orbital interactions can be considered to be the two most important stabilizing factors of the gauche form in the vicinal diazido fragment. The interplay of all three stabilizing interactions determines the gauche preference in the amine. Stereoelectronic effects, which are involved in orbital interactions, contribute to the gauche effect in all the molecules except the 2-azidoethylammonium ion and protonated 2-azidoethanol. Hydrogen-bonding interactions were found only in the protonated alcohol.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "New Journal of Chemistry",
title = "Theoretical study of azido gauche effect and its origin",
volume = "41",
number = "11",
pages = "4644-4661",
doi = "10.1039/c7nj00369b"
}

Baranac-Stojanović, M., Stojanović, M.,& Aleksić, J.. (2017). Theoretical study of azido gauche effect and its origin. in New Journal of Chemistry
Royal Soc Chemistry, Cambridge., 41(11), 4644-4661.
https://doi.org/10.1039/c7nj00369b

Baranac-Stojanović M, Stojanović M, Aleksić J. Theoretical study of azido gauche effect and its origin. in New Journal of Chemistry. 2017;41(11):4644-4661.
doi:10.1039/c7nj00369b .

Baranac-Stojanović, Marija, Stojanović, Milovan, Aleksić, Jovana, "Theoretical study of azido gauche effect and its origin" in New Journal of Chemistry, 41, no. 11 (2017):4644-4661,
https://doi.org/10.1039/c7nj00369b . .

TY  - JOUR
AU  - Rašović, Aleksandar
AU  - Blagojević, Vladimir A.
AU  - Baranac-Stojanović, Marija
AU  - Kleinpeter, Erich
AU  - Marković, Rade
AU  - Minić, Dragica M.
PY  - 2016
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1934
AB  - Information about the strength of donor-acceptor interactions in push-pull alkenes is valuable, as this so-called "push-pull effect'' influences their chemical reactivity and dynamic behaviour. In this paper, we discuss the applicability of NMR spectral data and barriers to rotation around the CQC double bond to quantify the push-pull effect in biologically important 2-alkylidene-4-oxothiazolidines. While olefinic proton chemical shifts and differences in C-13 NMR chemical shifts of the two carbons constituting the CQC double bond fail to give the correct trend in the electron withdrawing ability of the substituents attached to the exocyclic carbon of the double bond, barriers to rotation prove to be a reliable quantity in providing information about the extent of donor-acceptor interactions in the push-pull systems studied. In particular all relevant kinetic data, that is the Arrhenius parameters ( apparent activation energy Ea and frequency factor A) and activation parameters ( Delta S-double dagger, Delta H-double dagger and Delta G(double dagger)), were determined from the data of the experimentally studied configurational isomerization of ( E)-9a. These results were compared to previously published related data for other two compounds, ( Z)-1b and ( 2E, 5Z)-7, showing that experimentally determined Delta G(double dagger) values are a good indicator of the strength of push-pull character. Theoretical calculations of the rotational barriers of eight selected derivatives excellently correlate with the calculated CQC bond lengths and corroborate the applicability of Delta G(double dagger) for estimation of the strength of the push-pull effect in these and related systems.
PB  - Royal Soc Chemistry, Cambridge
T2  - New Journal of Chemistry
T1  - Quantification of the push-pull effect in 2-alkylidene-4-oxothiazolidines by using NMR spectral data and barriers to rotation around the C=C bond
VL  - 40
IS  - 7
SP  - 6364
EP  - 6373
DO  - 10.1039/c6nj00901h
ER  - 

@article{
author = "Rašović, Aleksandar and Blagojević, Vladimir A. and Baranac-Stojanović, Marija and Kleinpeter, Erich and Marković, Rade and Minić, Dragica M.",
year = "2016",
abstract = "Information about the strength of donor-acceptor interactions in push-pull alkenes is valuable, as this so-called "push-pull effect'' influences their chemical reactivity and dynamic behaviour. In this paper, we discuss the applicability of NMR spectral data and barriers to rotation around the CQC double bond to quantify the push-pull effect in biologically important 2-alkylidene-4-oxothiazolidines. While olefinic proton chemical shifts and differences in C-13 NMR chemical shifts of the two carbons constituting the CQC double bond fail to give the correct trend in the electron withdrawing ability of the substituents attached to the exocyclic carbon of the double bond, barriers to rotation prove to be a reliable quantity in providing information about the extent of donor-acceptor interactions in the push-pull systems studied. In particular all relevant kinetic data, that is the Arrhenius parameters ( apparent activation energy Ea and frequency factor A) and activation parameters ( Delta S-double dagger, Delta H-double dagger and Delta G(double dagger)), were determined from the data of the experimentally studied configurational isomerization of ( E)-9a. These results were compared to previously published related data for other two compounds, ( Z)-1b and ( 2E, 5Z)-7, showing that experimentally determined Delta G(double dagger) values are a good indicator of the strength of push-pull character. Theoretical calculations of the rotational barriers of eight selected derivatives excellently correlate with the calculated CQC bond lengths and corroborate the applicability of Delta G(double dagger) for estimation of the strength of the push-pull effect in these and related systems.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "New Journal of Chemistry",
title = "Quantification of the push-pull effect in 2-alkylidene-4-oxothiazolidines by using NMR spectral data and barriers to rotation around the C=C bond",
volume = "40",
number = "7",
pages = "6364-6373",
doi = "10.1039/c6nj00901h"
}

Rašović, A., Blagojević, V. A., Baranac-Stojanović, M., Kleinpeter, E., Marković, R.,& Minić, D. M.. (2016). Quantification of the push-pull effect in 2-alkylidene-4-oxothiazolidines by using NMR spectral data and barriers to rotation around the C=C bond. in New Journal of Chemistry
Royal Soc Chemistry, Cambridge., 40(7), 6364-6373.
https://doi.org/10.1039/c6nj00901h

Rašović A, Blagojević VA, Baranac-Stojanović M, Kleinpeter E, Marković R, Minić DM. Quantification of the push-pull effect in 2-alkylidene-4-oxothiazolidines by using NMR spectral data and barriers to rotation around the C=C bond. in New Journal of Chemistry. 2016;40(7):6364-6373.
doi:10.1039/c6nj00901h .

Rašović, Aleksandar, Blagojević, Vladimir A., Baranac-Stojanović, Marija, Kleinpeter, Erich, Marković, Rade, Minić, Dragica M., "Quantification of the push-pull effect in 2-alkylidene-4-oxothiazolidines by using NMR spectral data and barriers to rotation around the C=C bond" in New Journal of Chemistry, 40, no. 7 (2016):6364-6373,
https://doi.org/10.1039/c6nj00901h . .

TY  - JOUR
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2016
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1974
AB  - Substitution of a CH group in benzene with nitrogen has a little effect on its aromaticity (Wang et al, Org. Lett. 2010, 12, 4824). How does the same type of substitution affect aromatic character of the three isomeric azaborines? Does further protonation change aromaticity of diazaborines? This work is aimed at answering these questions. Such a knowledge should be of interest for further exploration and application of BN/CC isosterism. Aromaticity of diazaborines and their protonated forms is studied with the aid of four aromaticity indices, HOMA, NICS(0)(pi zz), PDI and ECRE. Generally, NICS(0)(pi zz) and PDI point to similar aromaticity of diazaborines and their parent azaborines, while HOMA and ECRE indicate some changes. Thus, aromaticity of 1,2-azaborine slightly decreases/increases when CH meta/ortho,para to B is substituted with nitrogen. Aromaticity of the most aromatic 1,3-azaborine remains almost unchanged when CH meta to B and N is replaced with nitrogen, and becomes slightly weaker when any other CH group is substituted with nitrogen. Replacement of the CH ortho to N in 1,4-azaborine does not change much its cyclic delocalization, while replacement of the CH ortho to B leads to smaller cyclic delocalization. Protonated forms are either of similar or decreased aromaticity compared with neutral molecules.
PB  - American Chemical Society (ACS)
T2  - Journal of Organic Chemistry
T1  - Aromaticity of Diazaborines and Their Protonated Forms
VL  - 81
IS  - 1
SP  - 197
EP  - 205
DO  - 10.1021/acs.joc.5b02499
ER  - 

@article{
author = "Stojanović, Milovan and Baranac-Stojanović, Marija",
year = "2016",
abstract = "Substitution of a CH group in benzene with nitrogen has a little effect on its aromaticity (Wang et al, Org. Lett. 2010, 12, 4824). How does the same type of substitution affect aromatic character of the three isomeric azaborines? Does further protonation change aromaticity of diazaborines? This work is aimed at answering these questions. Such a knowledge should be of interest for further exploration and application of BN/CC isosterism. Aromaticity of diazaborines and their protonated forms is studied with the aid of four aromaticity indices, HOMA, NICS(0)(pi zz), PDI and ECRE. Generally, NICS(0)(pi zz) and PDI point to similar aromaticity of diazaborines and their parent azaborines, while HOMA and ECRE indicate some changes. Thus, aromaticity of 1,2-azaborine slightly decreases/increases when CH meta/ortho,para to B is substituted with nitrogen. Aromaticity of the most aromatic 1,3-azaborine remains almost unchanged when CH meta to B and N is replaced with nitrogen, and becomes slightly weaker when any other CH group is substituted with nitrogen. Replacement of the CH ortho to N in 1,4-azaborine does not change much its cyclic delocalization, while replacement of the CH ortho to B leads to smaller cyclic delocalization. Protonated forms are either of similar or decreased aromaticity compared with neutral molecules.",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Organic Chemistry",
title = "Aromaticity of Diazaborines and Their Protonated Forms",
volume = "81",
number = "1",
pages = "197-205",
doi = "10.1021/acs.joc.5b02499"
}

Stojanović, M.,& Baranac-Stojanović, M.. (2016). Aromaticity of Diazaborines and Their Protonated Forms. in Journal of Organic Chemistry
American Chemical Society (ACS)., 81(1), 197-205.
https://doi.org/10.1021/acs.joc.5b02499

Stojanović M, Baranac-Stojanović M. Aromaticity of Diazaborines and Their Protonated Forms. in Journal of Organic Chemistry. 2016;81(1):197-205.
doi:10.1021/acs.joc.5b02499 .

Stojanović, Milovan, Baranac-Stojanović, Marija, "Aromaticity of Diazaborines and Their Protonated Forms" in Journal of Organic Chemistry, 81, no. 1 (2016):197-205,
https://doi.org/10.1021/acs.joc.5b02499 . .

TY  - JOUR
AU  - Stojanović, Milovan
AU  - Aleksić, Jovana
AU  - Baranac-Stojanović, Marija
PY  - 2015
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1628
AB  - The origin of the rotational barriers in n-butane and gauche conformational energy, the prototypes of steric repulsion, has been re-examined by using energy decomposition analysis. The Pauli repulsion was found to be an important factor, but not the source of the barriers and gauche/anti energy difference. Rather, it should be considered as a driving force for structural changes accompanying the rotation. The repulsion (steric) energy partly transfers into the deformation energy of ethyl fragments and also affects a decrease in electrostatic, orbital and dispersion interactions by inducing the structural changes, particularly the central CC bond lengthening, while it becomes less destabilizing during the anti-butane rotation.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Tetrahedron
T1  - The effect of steric repulsion on the torsional potential of n-butane: a theoretical study
VL  - 71
IS  - 32
SP  - 5119
EP  - 5123
DO  - 10.1016/j.tet.2015.06.002
ER  - 

@article{
author = "Stojanović, Milovan and Aleksić, Jovana and Baranac-Stojanović, Marija",
year = "2015",
abstract = "The origin of the rotational barriers in n-butane and gauche conformational energy, the prototypes of steric repulsion, has been re-examined by using energy decomposition analysis. The Pauli repulsion was found to be an important factor, but not the source of the barriers and gauche/anti energy difference. Rather, it should be considered as a driving force for structural changes accompanying the rotation. The repulsion (steric) energy partly transfers into the deformation energy of ethyl fragments and also affects a decrease in electrostatic, orbital and dispersion interactions by inducing the structural changes, particularly the central CC bond lengthening, while it becomes less destabilizing during the anti-butane rotation.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Tetrahedron",
title = "The effect of steric repulsion on the torsional potential of n-butane: a theoretical study",
volume = "71",
number = "32",
pages = "5119-5123",
doi = "10.1016/j.tet.2015.06.002"
}

Stojanović, M., Aleksić, J.,& Baranac-Stojanović, M.. (2015). The effect of steric repulsion on the torsional potential of n-butane: a theoretical study. in Tetrahedron
Oxford : Pergamon-Elsevier Science Ltd., 71(32), 5119-5123.
https://doi.org/10.1016/j.tet.2015.06.002

Stojanović M, Aleksić J, Baranac-Stojanović M. The effect of steric repulsion on the torsional potential of n-butane: a theoretical study. in Tetrahedron. 2015;71(32):5119-5123.
doi:10.1016/j.tet.2015.06.002 .

Stojanović, Milovan, Aleksić, Jovana, Baranac-Stojanović, Marija, "The effect of steric repulsion on the torsional potential of n-butane: a theoretical study" in Tetrahedron, 71, no. 32 (2015):5119-5123,
https://doi.org/10.1016/j.tet.2015.06.002 . .

TY  - JOUR
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2015
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1711
AB  - Various borenium ion affinities toward three ligands (L' = NH3, HCHO and Cl-) have been evaluated by DFT calculations in the gas-phase and in solvent (CH2Cl2). The gas-phase results have been rationalized on the basis of quantitative decomposition of the total binding energy into contributions from electrostatic, orbital, dispersion and Pauli interactions, and energy needed to deform the interacting fragments from their optimal geometry to that they adopt in an adduct. Twenty six borenium cations, differing in the type of the two R/R' substituents covalently bound to the boron atom and the neutral stabilizing ligand L, have been examined. With a few exceptions, the most important stabilizing interaction is electrostatic, more pronounced in the case of the charged ligand Cl-. Next come orbital interactions, involving the coordinate covalent bond formation, other charge transfer interactions between the cation and ligand, and polarization. Dispersion forces provide the smallest attraction, except in four complexes with long B-L' distances. We present how substituent (R/R')/ligand (L) variations affect binding enthalpies (Delta H)/energies (Delta E). Our results also show that the observed trend in the magnitudes of Delta Hs/Delta Es represents an interplay of the above mentioned (de) stabilizing energies, and can be explained by consideration of the boron-ligand distance and all charge/orbital interactions, rather than partial ones involving boron and ligand L'. Under solvent conditions, the Cl- affinities are drastically reduced and made very similar to NH3 affinities, but still larger than HCHO affinities.
PB  - Royal Soc Chemistry, Cambridge
T2  - RSC Advances
T1  - A theoretical study on borenium ion affinities toward ammonia, formaldehyde and chloride anions
VL  - 5
IS  - 93
SP  - 75895
EP  - 75910
DO  - 10.1039/c5ra13825f
ER  - 

@article{
author = "Stojanović, Milovan and Baranac-Stojanović, Marija",
year = "2015",
abstract = "Various borenium ion affinities toward three ligands (L' = NH3, HCHO and Cl-) have been evaluated by DFT calculations in the gas-phase and in solvent (CH2Cl2). The gas-phase results have been rationalized on the basis of quantitative decomposition of the total binding energy into contributions from electrostatic, orbital, dispersion and Pauli interactions, and energy needed to deform the interacting fragments from their optimal geometry to that they adopt in an adduct. Twenty six borenium cations, differing in the type of the two R/R' substituents covalently bound to the boron atom and the neutral stabilizing ligand L, have been examined. With a few exceptions, the most important stabilizing interaction is electrostatic, more pronounced in the case of the charged ligand Cl-. Next come orbital interactions, involving the coordinate covalent bond formation, other charge transfer interactions between the cation and ligand, and polarization. Dispersion forces provide the smallest attraction, except in four complexes with long B-L' distances. We present how substituent (R/R')/ligand (L) variations affect binding enthalpies (Delta H)/energies (Delta E). Our results also show that the observed trend in the magnitudes of Delta Hs/Delta Es represents an interplay of the above mentioned (de) stabilizing energies, and can be explained by consideration of the boron-ligand distance and all charge/orbital interactions, rather than partial ones involving boron and ligand L'. Under solvent conditions, the Cl- affinities are drastically reduced and made very similar to NH3 affinities, but still larger than HCHO affinities.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "RSC Advances",
title = "A theoretical study on borenium ion affinities toward ammonia, formaldehyde and chloride anions",
volume = "5",
number = "93",
pages = "75895-75910",
doi = "10.1039/c5ra13825f"
}

Stojanović, M.,& Baranac-Stojanović, M.. (2015). A theoretical study on borenium ion affinities toward ammonia, formaldehyde and chloride anions. in RSC Advances
Royal Soc Chemistry, Cambridge., 5(93), 75895-75910.
https://doi.org/10.1039/c5ra13825f

Stojanović M, Baranac-Stojanović M. A theoretical study on borenium ion affinities toward ammonia, formaldehyde and chloride anions. in RSC Advances. 2015;5(93):75895-75910.
doi:10.1039/c5ra13825f .

Stojanović, Milovan, Baranac-Stojanović, Marija, "A theoretical study on borenium ion affinities toward ammonia, formaldehyde and chloride anions" in RSC Advances, 5, no. 93 (2015):75895-75910,
https://doi.org/10.1039/c5ra13825f . .