Stojanović, Milovan

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Authority KeyName Variants
orcid::0000-0001-6890-9921
  • Stojanović, Milovan (39)
  • Stojanovic, M (5)

Author's Bibliography

Supplementary data for the article: Baranac-Stojanović, M.; Stojanović, M.; Aleksić, J. Triplet State (Anti)Aromaticity of Some Monoheterocyclic Analogues of Benzene, Naphthalene and Anthracene. New J. Chem. 2021, 45 (11), 5060–5074. https://doi.org/10.1039/D1NJ00207D.

Baranac-Stojanović, Marija; Stojanović, Milovan; Aleksić, Jovana

(Royal Society of Chemistry, 2021)

TY  - BOOK
AU  - Baranac-Stojanović, Marija
AU  - Stojanović, Milovan
AU  - Aleksić, Jovana
PY  - 2021
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/4356
PB  - Royal Society of Chemistry
T2  - New Journal of Chemistry
T1  - Supplementary data for the article: Baranac-Stojanović, M.; Stojanović, M.; Aleksić, J. Triplet State (Anti)Aromaticity of Some Monoheterocyclic Analogues of Benzene, Naphthalene and Anthracene. New J. Chem. 2021, 45 (11), 5060–5074. https://doi.org/10.1039/D1NJ00207D.
ER  - 
@book{
author = "Baranac-Stojanović, Marija and Stojanović, Milovan and Aleksić, Jovana",
year = "2021",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/4356",
publisher = "Royal Society of Chemistry",
journal = "New Journal of Chemistry",
title = "Supplementary data for the article: Baranac-Stojanović, M.; Stojanović, M.; Aleksić, J. Triplet State (Anti)Aromaticity of Some Monoheterocyclic Analogues of Benzene, Naphthalene and Anthracene. New J. Chem. 2021, 45 (11), 5060–5074. https://doi.org/10.1039/D1NJ00207D."
}
Baranac-Stojanović, M., Stojanović, M.,& Aleksić, J. (2021). Supplementary data for the article: Baranac-Stojanović, M.; Stojanović, M.; Aleksić, J. Triplet State (Anti)Aromaticity of Some Monoheterocyclic Analogues of Benzene, Naphthalene and Anthracene. New J. Chem. 2021, 45 (11), 5060–5074. https://doi.org/10.1039/D1NJ00207D..
New Journal of Chemistry
Royal Society of Chemistry..
Baranac-Stojanović M, Stojanović M, Aleksić J. Supplementary data for the article: Baranac-Stojanović, M.; Stojanović, M.; Aleksić, J. Triplet State (Anti)Aromaticity of Some Monoheterocyclic Analogues of Benzene, Naphthalene and Anthracene. New J. Chem. 2021, 45 (11), 5060–5074. https://doi.org/10.1039/D1NJ00207D.. New Journal of Chemistry. 2021;
Baranac-Stojanović Marija, Stojanović Milovan, Aleksić Jovana, "Supplementary data for the article: Baranac-Stojanović, M.; Stojanović, M.; Aleksić, J. Triplet State (Anti)Aromaticity of Some Monoheterocyclic Analogues of Benzene, Naphthalene and Anthracene. New J. Chem. 2021, 45 (11), 5060–5074. https://doi.org/10.1039/D1NJ00207D." New Journal of Chemistry (2021)

Triplet state (anti)aromaticity of some monoheterocyclic analogues of benzene, naphthalene and anthracene

Baranac-Stojanović, Marija; Stojanović, Milovan; Aleksić, Jovana

(Royal Society of Chemistry, 2021)

TY  - JOUR
AU  - Baranac-Stojanović, Marija
AU  - Stojanović, Milovan
AU  - Aleksić, Jovana
PY  - 2021
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/4355
AB  - Aromaticity–antiaromaticity switch upon singlet–triplet transition of some biologically and synthetically important monoheterocycles (heteroatom = N, O, Si, P, and S) derived from benzene, naphthalene and anthracene was studied by employing energetic, magnetic and structural aromaticity criteria, at the density functional theory (DFT) level. The relationship between spin density distribution, (anti)aromaticity and singlet–triplet energy gaps, in the studied molecules, was found. In general, spin delocalization results in antiaromaticity, spin density localization to one ring in bi- and tricycles localizes antiaromaticity and spin localization on a heteroatom reduces global and local antiaromaticity. The latter reaches nonaromaticity in the case of silicon atoms which have larger orbitals and show more tendency to accept unpaired electrons. Spin density localization in bi- and tricycles allows benzene subunit(s) to develop local aromaticity, which, when combined with nonaromatic silacycle and weak global antiaromaticity, results in overall triplet state weak aromaticity. The singlet–triplet energy gaps decrease with a decrease in the triplet state antiaromaticity and are the lowest for silicon-containing compounds.
PB  - Royal Society of Chemistry
T2  - New Journal of Chemistry
T1  - Triplet state (anti)aromaticity of some monoheterocyclic analogues of benzene, naphthalene and anthracene
VL  - 45
IS  - 11
SP  - 5060
EP  - 5074
DO  - 10.1039/D1NJ00207D
ER  - 
@article{
author = "Baranac-Stojanović, Marija and Stojanović, Milovan and Aleksić, Jovana",
year = "2021",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/4355",
abstract = "Aromaticity–antiaromaticity switch upon singlet–triplet transition of some biologically and synthetically important monoheterocycles (heteroatom = N, O, Si, P, and S) derived from benzene, naphthalene and anthracene was studied by employing energetic, magnetic and structural aromaticity criteria, at the density functional theory (DFT) level. The relationship between spin density distribution, (anti)aromaticity and singlet–triplet energy gaps, in the studied molecules, was found. In general, spin delocalization results in antiaromaticity, spin density localization to one ring in bi- and tricycles localizes antiaromaticity and spin localization on a heteroatom reduces global and local antiaromaticity. The latter reaches nonaromaticity in the case of silicon atoms which have larger orbitals and show more tendency to accept unpaired electrons. Spin density localization in bi- and tricycles allows benzene subunit(s) to develop local aromaticity, which, when combined with nonaromatic silacycle and weak global antiaromaticity, results in overall triplet state weak aromaticity. The singlet–triplet energy gaps decrease with a decrease in the triplet state antiaromaticity and are the lowest for silicon-containing compounds.",
publisher = "Royal Society of Chemistry",
journal = "New Journal of Chemistry",
title = "Triplet state (anti)aromaticity of some monoheterocyclic analogues of benzene, naphthalene and anthracene",
volume = "45",
number = "11",
pages = "5060-5074",
doi = "10.1039/D1NJ00207D"
}
Baranac-Stojanović, M., Stojanović, M.,& Aleksić, J. (2021). Triplet state (anti)aromaticity of some monoheterocyclic analogues of benzene, naphthalene and anthracene.
New Journal of Chemistry
Royal Society of Chemistry., 45(11), 5060-5074.
https://doi.org/10.1039/D1NJ00207D
Baranac-Stojanović M, Stojanović M, Aleksić J. Triplet state (anti)aromaticity of some monoheterocyclic analogues of benzene, naphthalene and anthracene. New Journal of Chemistry. 2021;45(11):5060-5074
Baranac-Stojanović Marija, Stojanović Milovan, Aleksić Jovana, "Triplet state (anti)aromaticity of some monoheterocyclic analogues of benzene, naphthalene and anthracene" New Journal of Chemistry, 45, no. 11 (2021):5060-5074,
https://doi.org/10.1039/D1NJ00207D .

Supplementary data for article: 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. Physical Chemistry Chemical Physics 2019, 21 (18), 9465–9476. https://doi.org/10.1039/c9cp01011d

Baranac-Stojanović, Marija; Stojanović, Milovan

(Royal Society of Chemistry, 2019)

TY  - BOOK
AU  - Baranac-Stojanović, Marija
AU  - Stojanović, Milovan
PY  - 2019
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3131
PB  - Royal Society of Chemistry
T2  - Physical Chemistry Chemical Physics
T1  - Supplementary data for article: 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. Physical Chemistry Chemical Physics 2019, 21 (18), 9465–9476. https://doi.org/10.1039/c9cp01011d
ER  - 
@book{
author = "Baranac-Stojanović, Marija and Stojanović, Milovan",
year = "2019",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3131",
publisher = "Royal Society of Chemistry",
journal = "Physical Chemistry Chemical Physics",
title = "Supplementary data for article: 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. Physical Chemistry Chemical Physics 2019, 21 (18), 9465–9476. https://doi.org/10.1039/c9cp01011d"
}
Baranac-Stojanović, M.,& Stojanović, M. (2019). Supplementary data for article: 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. Physical Chemistry Chemical Physics 2019, 21 (18), 9465–9476. https://doi.org/10.1039/c9cp01011d.
Physical Chemistry Chemical Physics
Royal Society of Chemistry..
Baranac-Stojanović M, Stojanović M. Supplementary data for article: 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. Physical Chemistry Chemical Physics 2019, 21 (18), 9465–9476. https://doi.org/10.1039/c9cp01011d. Physical Chemistry Chemical Physics. 2019;
Baranac-Stojanović Marija, Stojanović Milovan, "Supplementary data for article: 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. Physical Chemistry Chemical Physics 2019, 21 (18), 9465–9476. https://doi.org/10.1039/c9cp01011d" Physical Chemistry Chemical Physics (2019)

Does aromaticity account for an enhanced thermodynamic stability? The case of monosubstituted azaborines and the stereoelectronic chameleonism of the NH2 group

Baranac-Stojanović, Marija; Stojanović, Milovan

(Royal Society of Chemistry, 2019)

TY  - JOUR
AU  - Baranac-Stojanović, Marija
AU  - Stojanović, Milovan
PY  - 2019
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3130
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 NH 2 group from the usual p-electron donor to a π-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 N LP in the plane of the ring and the NH bonds in a favourable spatial position to act as acceptors of π-electron density.
PB  - Royal Society of Chemistry
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",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3130",
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 NH 2 group from the usual p-electron donor to a π-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 N LP in the plane of the ring and the NH bonds in a favourable spatial position to act as acceptors of π-electron density.",
publisher = "Royal Society of Chemistry",
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.
Physical Chemistry Chemical Physics
Royal Society of Chemistry., 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. Physical Chemistry Chemical Physics. 2019;21(18):9465-9476
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" Physical Chemistry Chemical Physics, 21, no. 18 (2019):9465-9476,
https://doi.org/10.1039/C9CP01011D .
1
2
2

Does aromaticity account for an enhanced thermodynamic stability? The case of monosubstituted azaborines and the stereoelectronic chameleonism of the NH2 group

Baranac-Stojanović, Marija; Stojanović, Milovan

(Royal Society of Chemistry, 2019)

TY  - JOUR
AU  - Baranac-Stojanović, Marija
AU  - Stojanović, Milovan
PY  - 2019
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3128
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 NH 2 group from the usual p-electron donor to a π-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 N LP in the plane of the ring and the NH bonds in a favourable spatial position to act as acceptors of π-electron density.
PB  - Royal Society of Chemistry
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",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3128",
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 NH 2 group from the usual p-electron donor to a π-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 N LP in the plane of the ring and the NH bonds in a favourable spatial position to act as acceptors of π-electron density.",
publisher = "Royal Society of Chemistry",
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.
Physical Chemistry Chemical Physics
Royal Society of Chemistry., 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. Physical Chemistry Chemical Physics. 2019;21(18):9465-9476
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" Physical Chemistry Chemical Physics, 21, no. 18 (2019):9465-9476,
https://doi.org/10.1039/C9CP01011D .
1
2
2

The effect of two types of dibenzoannulation of pentalene on molecular energies and magnetically induced currents

Baranac-Stojanović, Marija; Stojanović, Milovan

(Royal Society of Chemistry, 2019)

TY  - JOUR
AU  - Baranac-Stojanović, Marija
AU  - Stojanović, Milovan
PY  - 2019
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2863
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",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2863",
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.
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. Physical Chemistry Chemical Physics. 2019;21(6):3250-3263
Baranac-Stojanović Marija, Stojanović Milovan, "The effect of two types of dibenzoannulation of pentalene on molecular energies and magnetically induced currents" Physical Chemistry Chemical Physics, 21, no. 6 (2019):3250-3263,
https://doi.org/10.1039/c8cp07875k .
1
4
3
4

The effect of two types of dibenzoannulation of pentalene on molecular energies and magnetically induced currents

Baranac-Stojanović, Marija; Stojanović, Milovan

(Royal Society of Chemistry, 2019)

TY  - JOUR
AU  - Baranac-Stojanović, Marija
AU  - Stojanović, Milovan
PY  - 2019
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2847
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",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2847",
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.
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. Physical Chemistry Chemical Physics. 2019;21(6):3250-3263
Baranac-Stojanović Marija, Stojanović Milovan, "The effect of two types of dibenzoannulation of pentalene on molecular energies and magnetically induced currents" Physical Chemistry Chemical Physics, 21, no. 6 (2019):3250-3263,
https://doi.org/10.1039/c8cp07875k .
1
4
3
4

Supplementary material for the article: 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. New Journal of Chemistry 2018, 42 (15), 12968–12976. https://doi.org/10.1039/c8nj01529e

Stojanović, Milovan; Baranac-Stojanović, Marija

(Royal Soc Chemistry, Cambridge, 2018)

TY  - BOOK
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2018
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3241
PB  - Royal Soc Chemistry, Cambridge
T2  - New Journal of Chemistry
T1  - Supplementary material for the article: 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. New Journal of Chemistry 2018, 42 (15), 12968–12976. https://doi.org/10.1039/c8nj01529e
ER  - 
@book{
author = "Stojanović, Milovan and Baranac-Stojanović, Marija",
year = "2018",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3241",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "New Journal of Chemistry",
title = "Supplementary material for the article: 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. New Journal of Chemistry 2018, 42 (15), 12968–12976. https://doi.org/10.1039/c8nj01529e"
}
Stojanović, M.,& Baranac-Stojanović, M. (2018). Supplementary material for the article: 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. New Journal of Chemistry 2018, 42 (15), 12968–12976. https://doi.org/10.1039/c8nj01529e.
New Journal of Chemistry
Royal Soc Chemistry, Cambridge..
Stojanović M, Baranac-Stojanović M. Supplementary material for the article: 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. New Journal of Chemistry 2018, 42 (15), 12968–12976. https://doi.org/10.1039/c8nj01529e. New Journal of Chemistry. 2018;
Stojanović Milovan, Baranac-Stojanović Marija, "Supplementary material for the article: 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. New Journal of Chemistry 2018, 42 (15), 12968–12976. https://doi.org/10.1039/c8nj01529e" New Journal of Chemistry (2018)

Mono BN-substituted analogues of naphthalene: a theoretical analysis of the effect of BN position on stability, aromaticity and frontier orbital energies

Stojanović, Milovan; Baranac-Stojanović, Marija

(Royal Soc Chemistry, Cambridge, 2018)

TY  - JOUR
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2018
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3240
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",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3240",
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.
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. New Journal of Chemistry. 2018;42(15):12968-12976
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" New Journal of Chemistry, 42, no. 15 (2018):12968-12976,
https://doi.org/10.1039/c8nj01529e .
4
4
7

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

Aleksić, Jovana; Stojanović, Milovan; Baranac-Stojanović, Marija

(Wiley-V C H Verlag Gmbh, Weinheim, 2018)

TY  - JOUR
AU  - Aleksić, Jovana
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2018
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2947
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",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2947",
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.
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. Chemistry. An Asian Journal. 2018;13(14):1811-1835
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" Chemistry. An Asian Journal, 13, no. 14 (2018):1811-1835,
https://doi.org/10.1002/asia.201800645 .
1
3
3
5

Mono BN-substituted analogues of naphthalene: a theoretical analysis of the effect of BN position on stability, aromaticity and frontier orbital energies

Stojanović, Milovan; Baranac-Stojanović, Marija

(Royal Soc Chemistry, Cambridge, 2018)

TY  - JOUR
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2018
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2227
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",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2227",
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.
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. New Journal of Chemistry. 2018;42(15):12968-12976
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" New Journal of Chemistry, 42, no. 15 (2018):12968-12976,
https://doi.org/10.1039/c8nj01529e .
4
4
7

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

Aleksić, Jovana; Stojanović, Milovan; Baranac-Stojanović, Marija

(Wiley-V C H Verlag Gmbh, Weinheim, 2018)

TY  - JOUR
AU  - Aleksić, Jovana
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2018
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2188
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",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2188",
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.
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. Chemistry. An Asian Journal. 2018;13(14):1811-1835
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" Chemistry. An Asian Journal, 13, no. 14 (2018):1811-1835,
https://doi.org/10.1002/asia.201800645 .
1
3
3
5

Supplementary material for the article: Baranac-Stojanović, M.; Stojanović, M.; Aleksić, J. Theoretical Study of Azido: Gauche Effect and Its Origin. New Journal of Chemistry 2017, 41 (11), 4644–4661. https://doi.org/10.1039/c7nj00369b

Baranac-Stojanović, Marija; Stojanović, Milovan; Aleksić, Jovana

(Royal Soc Chemistry, Cambridge, 2017)

TY  - BOOK
AU  - Baranac-Stojanović, Marija
AU  - Stojanović, Milovan
AU  - Aleksić, Jovana
PY  - 2017
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3260
PB  - Royal Soc Chemistry, Cambridge
T2  - New Journal of Chemistry
T1  - Supplementary material for the article: Baranac-Stojanović, M.; Stojanović, M.; Aleksić, J. Theoretical Study of Azido: Gauche Effect and Its Origin. New Journal of Chemistry 2017, 41 (11), 4644–4661. https://doi.org/10.1039/c7nj00369b
ER  - 
@book{
author = "Baranac-Stojanović, Marija and Stojanović, Milovan and Aleksić, Jovana",
year = "2017",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3260",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "New Journal of Chemistry",
title = "Supplementary material for the article: Baranac-Stojanović, M.; Stojanović, M.; Aleksić, J. Theoretical Study of Azido: Gauche Effect and Its Origin. New Journal of Chemistry 2017, 41 (11), 4644–4661. https://doi.org/10.1039/c7nj00369b"
}
Baranac-Stojanović, M., Stojanović, M.,& Aleksić, J. (2017). Supplementary material for the article: Baranac-Stojanović, M.; Stojanović, M.; Aleksić, J. Theoretical Study of Azido: Gauche Effect and Its Origin. New Journal of Chemistry 2017, 41 (11), 4644–4661. https://doi.org/10.1039/c7nj00369b.
New Journal of Chemistry
Royal Soc Chemistry, Cambridge..
Baranac-Stojanović M, Stojanović M, Aleksić J. Supplementary material for the article: Baranac-Stojanović, M.; Stojanović, M.; Aleksić, J. Theoretical Study of Azido: Gauche Effect and Its Origin. New Journal of Chemistry 2017, 41 (11), 4644–4661. https://doi.org/10.1039/c7nj00369b. New Journal of Chemistry. 2017;
Baranac-Stojanović Marija, Stojanović Milovan, Aleksić Jovana, "Supplementary material for the article: Baranac-Stojanović, M.; Stojanović, M.; Aleksić, J. Theoretical Study of Azido: Gauche Effect and Its Origin. New Journal of Chemistry 2017, 41 (11), 4644–4661. https://doi.org/10.1039/c7nj00369b" New Journal of Chemistry (2017)

Theoretical study of azido gauche effect and its origin

Baranac-Stojanović, Marija; Stojanović, Milovan; Aleksić, Jovana

(Royal Soc Chemistry, Cambridge, 2017)

TY  - JOUR
AU  - Baranac-Stojanović, Marija
AU  - Stojanović, Milovan
AU  - Aleksić, Jovana
PY  - 2017
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2464
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",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2464",
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.
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. New Journal of Chemistry. 2017;41(11):4644-4661
Baranac-Stojanović Marija, Stojanović Milovan, Aleksić Jovana, "Theoretical study of azido gauche effect and its origin" New Journal of Chemistry, 41, no. 11 (2017):4644-4661,
https://doi.org/10.1039/c7nj00369b .
1
2
2

Supplementary material for the article: Stojanović, M.; Baranac-Stojanović, M. Aromaticity of Diazaborines and Their Protonated Forms. J. Org. Chem. 2016, 81 (1), 197–205. https://doi.org/10.1021/acs.joc.5b02499

Stojanović, Milovan; Baranac-Stojanović, Marija

(Amer Chemical Soc, Washington, 2016)

TY  - BOOK
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2016
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3372
PB  - Amer Chemical Soc, Washington
T2  - Journal of Organic Chemistry
T1  - Supplementary material for the article: Stojanović, M.; Baranac-Stojanović, M. Aromaticity of Diazaborines and Their Protonated Forms. J. Org. Chem. 2016, 81 (1), 197–205. https://doi.org/10.1021/acs.joc.5b02499
ER  - 
@book{
author = "Stojanović, Milovan and Baranac-Stojanović, Marija",
year = "2016",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3372",
publisher = "Amer Chemical Soc, Washington",
journal = "Journal of Organic Chemistry",
title = "Supplementary material for the article: Stojanović, M.; Baranac-Stojanović, M. Aromaticity of Diazaborines and Their Protonated Forms. J. Org. Chem. 2016, 81 (1), 197–205. https://doi.org/10.1021/acs.joc.5b02499"
}
Stojanović, M.,& Baranac-Stojanović, M. (2016). Supplementary material for the article: Stojanović, M.; Baranac-Stojanović, M. Aromaticity of Diazaborines and Their Protonated Forms. J. Org. Chem. 2016, 81 (1), 197–205. https://doi.org/10.1021/acs.joc.5b02499.
Journal of Organic Chemistry
Amer Chemical Soc, Washington..
Stojanović M, Baranac-Stojanović M. Supplementary material for the article: Stojanović, M.; Baranac-Stojanović, M. Aromaticity of Diazaborines and Their Protonated Forms. J. Org. Chem. 2016, 81 (1), 197–205. https://doi.org/10.1021/acs.joc.5b02499. Journal of Organic Chemistry. 2016;
Stojanović Milovan, Baranac-Stojanović Marija, "Supplementary material for the article: Stojanović, M.; Baranac-Stojanović, M. Aromaticity of Diazaborines and Their Protonated Forms. J. Org. Chem. 2016, 81 (1), 197–205. https://doi.org/10.1021/acs.joc.5b02499" Journal of Organic Chemistry (2016)

Aromaticity of Diazaborines and Their Protonated Forms

Stojanović, Milovan; Baranac-Stojanović, Marija

(Amer Chemical Soc, Washington, 2016)

TY  - JOUR
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2016
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2022
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  - Amer Chemical Soc, Washington
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",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2022",
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 = "Amer Chemical Soc, Washington",
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.
Journal of Organic Chemistry
Amer Chemical Soc, Washington., 81(1), 197-205.
https://doi.org/10.1021/acs.joc.5b02499
Stojanović M, Baranac-Stojanović M. Aromaticity of Diazaborines and Their Protonated Forms. Journal of Organic Chemistry. 2016;81(1):197-205
Stojanović Milovan, Baranac-Stojanović Marija, "Aromaticity of Diazaborines and Their Protonated Forms" Journal of Organic Chemistry, 81, no. 1 (2016):197-205,
https://doi.org/10.1021/acs.joc.5b02499 .
1
13
14
14

Supplementary data for article: Stojanović, M.; Aleksić, J.; Baranac-Stojanović, M. The Effect of Steric Repulsion on the Torsional Potential of N-Butane: A Theoretical Study. Tetrahedron 2015, 71 (32), 5119–5123. https://doi.org/10.1016/j.tet.2015.06.002

Stojanović, Milovan; Aleksić, Jovana; Baranac-Stojanović, Marija

(Pergamon-Elsevier Science Ltd, Oxford, 2015)

TY  - BOOK
AU  - Stojanović, Milovan
AU  - Aleksić, Jovana
AU  - Baranac-Stojanović, Marija
PY  - 2015
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3452
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Tetrahedron
T1  - Supplementary data for article: Stojanović, M.; Aleksić, J.; Baranac-Stojanović, M. The Effect of Steric Repulsion on the Torsional Potential of N-Butane: A Theoretical Study. Tetrahedron 2015, 71 (32), 5119–5123. https://doi.org/10.1016/j.tet.2015.06.002
ER  - 
@book{
author = "Stojanović, Milovan and Aleksić, Jovana and Baranac-Stojanović, Marija",
year = "2015",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3452",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron",
title = "Supplementary data for article: Stojanović, M.; Aleksić, J.; Baranac-Stojanović, M. The Effect of Steric Repulsion on the Torsional Potential of N-Butane: A Theoretical Study. Tetrahedron 2015, 71 (32), 5119–5123. https://doi.org/10.1016/j.tet.2015.06.002"
}
Stojanović, M., Aleksić, J.,& Baranac-Stojanović, M. (2015). Supplementary data for article: Stojanović, M.; Aleksić, J.; Baranac-Stojanović, M. The Effect of Steric Repulsion on the Torsional Potential of N-Butane: A Theoretical Study. Tetrahedron 2015, 71 (32), 5119–5123. https://doi.org/10.1016/j.tet.2015.06.002.
Tetrahedron
Pergamon-Elsevier Science Ltd, Oxford..
Stojanović M, Aleksić J, Baranac-Stojanović M. Supplementary data for article: Stojanović, M.; Aleksić, J.; Baranac-Stojanović, M. The Effect of Steric Repulsion on the Torsional Potential of N-Butane: A Theoretical Study. Tetrahedron 2015, 71 (32), 5119–5123. https://doi.org/10.1016/j.tet.2015.06.002. Tetrahedron. 2015;
Stojanović Milovan, Aleksić Jovana, Baranac-Stojanović Marija, "Supplementary data for article: Stojanović, M.; Aleksić, J.; Baranac-Stojanović, M. The Effect of Steric Repulsion on the Torsional Potential of N-Butane: A Theoretical Study. Tetrahedron 2015, 71 (32), 5119–5123. https://doi.org/10.1016/j.tet.2015.06.002" Tetrahedron (2015)

Supplementary data for article: Aleksić, J.; Stojanović, M.; Baranac-Stojanović, M. Origin of Fluorine/Sulfur Gauche Effect of β-Fluorinated Thiol, Sulfoxide, Sulfone, and Thionium Ion. Journal of Organic Chemistry 2015, 80 (20), 10197–10207. https://doi.org/10.1021/acs.joc.5b01779

Aleksić, Jovana; Stojanović, Milovan; Baranac-Stojanović, Marija

(Amer Chemical Soc, Washington, 2015)

TY  - BOOK
AU  - Aleksić, Jovana
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2015
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3401
PB  - Amer Chemical Soc, Washington
T2  - Journal of Organic Chemistry
T1  - Supplementary data for article: Aleksić, J.; Stojanović, M.; Baranac-Stojanović, M. Origin of Fluorine/Sulfur Gauche Effect of β-Fluorinated Thiol, Sulfoxide, Sulfone, and Thionium Ion. Journal of Organic Chemistry 2015, 80 (20), 10197–10207. https://doi.org/10.1021/acs.joc.5b01779
ER  - 
@book{
author = "Aleksić, Jovana and Stojanović, Milovan and Baranac-Stojanović, Marija",
year = "2015",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3401",
publisher = "Amer Chemical Soc, Washington",
journal = "Journal of Organic Chemistry",
title = "Supplementary data for article: Aleksić, J.; Stojanović, M.; Baranac-Stojanović, M. Origin of Fluorine/Sulfur Gauche Effect of β-Fluorinated Thiol, Sulfoxide, Sulfone, and Thionium Ion. Journal of Organic Chemistry 2015, 80 (20), 10197–10207. https://doi.org/10.1021/acs.joc.5b01779"
}
Aleksić, J., Stojanović, M.,& Baranac-Stojanović, M. (2015). Supplementary data for article: Aleksić, J.; Stojanović, M.; Baranac-Stojanović, M. Origin of Fluorine/Sulfur Gauche Effect of β-Fluorinated Thiol, Sulfoxide, Sulfone, and Thionium Ion. Journal of Organic Chemistry 2015, 80 (20), 10197–10207. https://doi.org/10.1021/acs.joc.5b01779.
Journal of Organic Chemistry
Amer Chemical Soc, Washington..
Aleksić J, Stojanović M, Baranac-Stojanović M. Supplementary data for article: Aleksić, J.; Stojanović, M.; Baranac-Stojanović, M. Origin of Fluorine/Sulfur Gauche Effect of β-Fluorinated Thiol, Sulfoxide, Sulfone, and Thionium Ion. Journal of Organic Chemistry 2015, 80 (20), 10197–10207. https://doi.org/10.1021/acs.joc.5b01779. Journal of Organic Chemistry. 2015;
Aleksić Jovana, Stojanović Milovan, Baranac-Stojanović Marija, "Supplementary data for article: Aleksić, J.; Stojanović, M.; Baranac-Stojanović, M. Origin of Fluorine/Sulfur Gauche Effect of β-Fluorinated Thiol, Sulfoxide, Sulfone, and Thionium Ion. Journal of Organic Chemistry 2015, 80 (20), 10197–10207. https://doi.org/10.1021/acs.joc.5b01779" Journal of Organic Chemistry (2015)

Supplementary data for the article: Stojanović, M.; Baranac-Stojanović, M. A Theoretical Study on Borenium Ion Affinities toward Ammonia, Formaldehyde and Chloride Anions. RSC Advances 2015, 5 (93), 75895–75910. https://doi.org/10.1039/c5ra13825f

Stojanović, Milovan; Baranac-Stojanović, Marija

(Royal Soc Chemistry, Cambridge, 2015)

TY  - BOOK
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2015
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3330
PB  - Royal Soc Chemistry, Cambridge
T2  - RSC Advances
T1  - Supplementary data for the article: Stojanović, M.; Baranac-Stojanović, M. A Theoretical Study on Borenium Ion Affinities toward Ammonia, Formaldehyde and Chloride Anions. RSC Advances 2015, 5 (93), 75895–75910. https://doi.org/10.1039/c5ra13825f
ER  - 
@book{
author = "Stojanović, Milovan and Baranac-Stojanović, Marija",
year = "2015",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3330",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "RSC Advances",
title = "Supplementary data for the article: Stojanović, M.; Baranac-Stojanović, M. A Theoretical Study on Borenium Ion Affinities toward Ammonia, Formaldehyde and Chloride Anions. RSC Advances 2015, 5 (93), 75895–75910. https://doi.org/10.1039/c5ra13825f"
}
Stojanović, M.,& Baranac-Stojanović, M. (2015). Supplementary data for the article: Stojanović, M.; Baranac-Stojanović, M. A Theoretical Study on Borenium Ion Affinities toward Ammonia, Formaldehyde and Chloride Anions. RSC Advances 2015, 5 (93), 75895–75910. https://doi.org/10.1039/c5ra13825f.
RSC Advances
Royal Soc Chemistry, Cambridge..
Stojanović M, Baranac-Stojanović M. Supplementary data for the article: Stojanović, M.; Baranac-Stojanović, M. A Theoretical Study on Borenium Ion Affinities toward Ammonia, Formaldehyde and Chloride Anions. RSC Advances 2015, 5 (93), 75895–75910. https://doi.org/10.1039/c5ra13825f. RSC Advances. 2015;
Stojanović Milovan, Baranac-Stojanović Marija, "Supplementary data for the article: Stojanović, M.; Baranac-Stojanović, M. A Theoretical Study on Borenium Ion Affinities toward Ammonia, Formaldehyde and Chloride Anions. RSC Advances 2015, 5 (93), 75895–75910. https://doi.org/10.1039/c5ra13825f" RSC Advances (2015)

Origin of Fluorine/Sulfur Gauche Effect of beta-Fluorinated Thiol, Sulfoxide, Sulfone, and Thionium Ion

Aleksić, Jovana; Stojanović, Milovan; Baranac-Stojanović, Marija

(Amer Chemical Soc, Washington, 2015)

TY  - JOUR
AU  - Aleksić, Jovana
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2015
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/1981
AB  - The well-known gauche preference in FCCX systems, where X is an electronegative element from Period 2, is widely exploited in synthetic, medicinal, and material chemistry. It is rationalized on the basis of sigma(C-H)- gt sigma*(C-F) hyperconjugation and electrostatic interactions. The recent report (Thiehoff, C.; et al. Chem. Sci. 2015, 6, 3565) showed that the fluorine gauche effect can extend to Period 3 elements, such as sulfur. The aim of the present work is to disclose factors governing conformational behavior of FCCS containing systems. We examine conformational preferences in seven classes of compounds by ab initio and DFT calculations and rationalize the results by quantitatively decomposing the anti/gauche isomerization energy into contributions from electrostatic, orbital, dispersion, and Pauli interactions, and energy spent on structural changes. The results show that the fluorine/sulfur gauche effect is primarily electrostatic (63-75%), while all orbital interactions contribute 22-41% to stabilizing interactions. Stereoelectronic effects, involved in orbital interactions, also play a role in gauche conformer stabilization.
PB  - Amer Chemical Soc, Washington
T2  - Journal of Organic Chemistry
T1  - Origin of Fluorine/Sulfur Gauche Effect of beta-Fluorinated Thiol, Sulfoxide, Sulfone, and Thionium Ion
VL  - 80
IS  - 20
SP  - 10197
EP  - 10207
DO  - 10.1021/acs.joc.5b01779
ER  - 
@article{
author = "Aleksić, Jovana and Stojanović, Milovan and Baranac-Stojanović, Marija",
year = "2015",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/1981",
abstract = "The well-known gauche preference in FCCX systems, where X is an electronegative element from Period 2, is widely exploited in synthetic, medicinal, and material chemistry. It is rationalized on the basis of sigma(C-H)- gt sigma*(C-F) hyperconjugation and electrostatic interactions. The recent report (Thiehoff, C.; et al. Chem. Sci. 2015, 6, 3565) showed that the fluorine gauche effect can extend to Period 3 elements, such as sulfur. The aim of the present work is to disclose factors governing conformational behavior of FCCS containing systems. We examine conformational preferences in seven classes of compounds by ab initio and DFT calculations and rationalize the results by quantitatively decomposing the anti/gauche isomerization energy into contributions from electrostatic, orbital, dispersion, and Pauli interactions, and energy spent on structural changes. The results show that the fluorine/sulfur gauche effect is primarily electrostatic (63-75%), while all orbital interactions contribute 22-41% to stabilizing interactions. Stereoelectronic effects, involved in orbital interactions, also play a role in gauche conformer stabilization.",
publisher = "Amer Chemical Soc, Washington",
journal = "Journal of Organic Chemistry",
title = "Origin of Fluorine/Sulfur Gauche Effect of beta-Fluorinated Thiol, Sulfoxide, Sulfone, and Thionium Ion",
volume = "80",
number = "20",
pages = "10197-10207",
doi = "10.1021/acs.joc.5b01779"
}
Aleksić, J., Stojanović, M.,& Baranac-Stojanović, M. (2015). Origin of Fluorine/Sulfur Gauche Effect of beta-Fluorinated Thiol, Sulfoxide, Sulfone, and Thionium Ion.
Journal of Organic Chemistry
Amer Chemical Soc, Washington., 80(20), 10197-10207.
https://doi.org/10.1021/acs.joc.5b01779
Aleksić J, Stojanović M, Baranac-Stojanović M. Origin of Fluorine/Sulfur Gauche Effect of beta-Fluorinated Thiol, Sulfoxide, Sulfone, and Thionium Ion. Journal of Organic Chemistry. 2015;80(20):10197-10207
Aleksić Jovana, Stojanović Milovan, Baranac-Stojanović Marija, "Origin of Fluorine/Sulfur Gauche Effect of beta-Fluorinated Thiol, Sulfoxide, Sulfone, and Thionium Ion" Journal of Organic Chemistry, 80, no. 20 (2015):10197-10207,
https://doi.org/10.1021/acs.joc.5b01779 .
15
14
16

A theoretical study on borenium ion affinities toward ammonia, formaldehyde and chloride anions

Stojanović, Milovan; Baranac-Stojanović, Marija

(Royal Soc Chemistry, Cambridge, 2015)

TY  - JOUR
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2015
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/1968
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",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/1968",
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.
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. RSC Advances. 2015;5(93):75895-75910
Stojanović Milovan, Baranac-Stojanović Marija, "A theoretical study on borenium ion affinities toward ammonia, formaldehyde and chloride anions" RSC Advances, 5, no. 93 (2015):75895-75910,
https://doi.org/10.1039/c5ra13825f .
3
1
1
1

The effect of steric repulsion on the torsional potential of n-butane: a theoretical study

Stojanović, Milovan; Aleksić, Jovana; Baranac-Stojanović, Marija

(Pergamon-Elsevier Science Ltd, Oxford, 2015)

TY  - JOUR
AU  - Stojanović, Milovan
AU  - Aleksić, Jovana
AU  - Baranac-Stojanović, Marija
PY  - 2015
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/1734
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  - Pergamon-Elsevier Science Ltd, Oxford
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",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/1734",
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 = "Pergamon-Elsevier Science Ltd, Oxford",
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.
Tetrahedron
Pergamon-Elsevier Science Ltd, Oxford., 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. Tetrahedron. 2015;71(32):5119-5123
Stojanović Milovan, Aleksić Jovana, Baranac-Stojanović Marija, "The effect of steric repulsion on the torsional potential of n-butane: a theoretical study" Tetrahedron, 71, no. 32 (2015):5119-5123,
https://doi.org/10.1016/j.tet.2015.06.002 .
9
8
9

Energy decomposition analysis of gauche preference in 2-haloethanol, 2-haloethylamine (halogen = F, Cl), their protonated forms and anti preference in 1-chloro-2-fluoroethane

Baranac-Stojanović, Marija; Aleksić, Jovana; Stojanović, Milovan

(Royal Soc Chemistry, Cambridge, 2015)

TY  - JOUR
AU  - Baranac-Stojanović, Marija
AU  - Aleksić, Jovana
AU  - Stojanović, Milovan
PY  - 2015
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/1669
AB  - 2-Haloethanol and 2-haloethylamine (halogen = F, Cl) prefer gauche conformation. This preference is significantly increased upon protonation. Commonly used explanations are based on intramolecular hydrogen bonding and hyperconjugation. 1,2-Difluoroethane prefers gauche conformation, too, while gaseous 1-chloro-2-fluoroethane is more stable as the anti conformer. The origin of these conformational preferences has been investigated by a quantitative partitioning of the gauche/anti energy difference into contributions from electrostatic, orbital, dispersion and Pauli interactions, and structural changes accompanying the rotation. The results show that, with two exceptions, the most important contributor to the gauche preference is electrostatic attraction, which is larger in gauche forms relative to the anti ones. Next come orbital interactions, while dispersion forces provide the smallest stabilizing energy. These energy components override destabilizing Pauli interactions and energetically costly structural changes. All gauche preferences also benefit from stereoelectronic effects, except in protonated 2-chloroethanol which, instead, shows a significant Cl lone pair - gt  O-H antibond mixing, associated with hydrogen bonding. The increase in the Pauli repulsion upon anti to gauche isomerization is more pronounced for fluorine than for chlorine derivatives. Thus, the smaller gauche effect in chloro-compounds and the anti preference in 1-chloro-2-fluoroethane have their origin in the decrease in electrostatic and orbital stabilizing interactions, a drop in the former being more pronounced.
PB  - Royal Soc Chemistry, Cambridge
T2  - RSC Advances
T1  - Energy decomposition analysis of gauche preference in 2-haloethanol, 2-haloethylamine (halogen = F, Cl), their protonated forms and anti preference in 1-chloro-2-fluoroethane
VL  - 5
IS  - 29
SP  - 22980
EP  - 22995
DO  - 10.1039/c5ra01164g
ER  - 
@article{
author = "Baranac-Stojanović, Marija and Aleksić, Jovana and Stojanović, Milovan",
year = "2015",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/1669",
abstract = "2-Haloethanol and 2-haloethylamine (halogen = F, Cl) prefer gauche conformation. This preference is significantly increased upon protonation. Commonly used explanations are based on intramolecular hydrogen bonding and hyperconjugation. 1,2-Difluoroethane prefers gauche conformation, too, while gaseous 1-chloro-2-fluoroethane is more stable as the anti conformer. The origin of these conformational preferences has been investigated by a quantitative partitioning of the gauche/anti energy difference into contributions from electrostatic, orbital, dispersion and Pauli interactions, and structural changes accompanying the rotation. The results show that, with two exceptions, the most important contributor to the gauche preference is electrostatic attraction, which is larger in gauche forms relative to the anti ones. Next come orbital interactions, while dispersion forces provide the smallest stabilizing energy. These energy components override destabilizing Pauli interactions and energetically costly structural changes. All gauche preferences also benefit from stereoelectronic effects, except in protonated 2-chloroethanol which, instead, shows a significant Cl lone pair - gt  O-H antibond mixing, associated with hydrogen bonding. The increase in the Pauli repulsion upon anti to gauche isomerization is more pronounced for fluorine than for chlorine derivatives. Thus, the smaller gauche effect in chloro-compounds and the anti preference in 1-chloro-2-fluoroethane have their origin in the decrease in electrostatic and orbital stabilizing interactions, a drop in the former being more pronounced.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "RSC Advances",
title = "Energy decomposition analysis of gauche preference in 2-haloethanol, 2-haloethylamine (halogen = F, Cl), their protonated forms and anti preference in 1-chloro-2-fluoroethane",
volume = "5",
number = "29",
pages = "22980-22995",
doi = "10.1039/c5ra01164g"
}
Baranac-Stojanović, M., Aleksić, J.,& Stojanović, M. (2015). Energy decomposition analysis of gauche preference in 2-haloethanol, 2-haloethylamine (halogen = F, Cl), their protonated forms and anti preference in 1-chloro-2-fluoroethane.
RSC Advances
Royal Soc Chemistry, Cambridge., 5(29), 22980-22995.
https://doi.org/10.1039/c5ra01164g
Baranac-Stojanović M, Aleksić J, Stojanović M. Energy decomposition analysis of gauche preference in 2-haloethanol, 2-haloethylamine (halogen = F, Cl), their protonated forms and anti preference in 1-chloro-2-fluoroethane. RSC Advances. 2015;5(29):22980-22995
Baranac-Stojanović Marija, Aleksić Jovana, Stojanović Milovan, "Energy decomposition analysis of gauche preference in 2-haloethanol, 2-haloethylamine (halogen = F, Cl), their protonated forms and anti preference in 1-chloro-2-fluoroethane" RSC Advances, 5, no. 29 (2015):22980-22995,
https://doi.org/10.1039/c5ra01164g .
12
13
14

4-Oxothiazolidines with Exocyclic C=C Double Bond(s): Synthesis, Structure, Reactions and Biological Activity

Stojanović, Milovan; Džambaski, Zdravko; Bondžić, Bojan; Aleksić, Jovana; Baranac-Stojanović, Marija

(Bentham Science Publ Ltd, Sharjah, 2014)

TY  - JOUR
AU  - Stojanović, Milovan
AU  - Džambaski, Zdravko
AU  - Bondžić, Bojan
AU  - Aleksić, Jovana
AU  - Baranac-Stojanović, Marija
PY  - 2014
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/1810
AB  - 4-Oxothiazolidine core, owing to the wide range of pharmacological activities exhibited by its derivatives, has been recognized as an important structural motif in biologically active compounds. A subclass constitutes 4-oxothiazolidines with an exocyclic C=C double bond at the C(2)-position. Some of these derivatives are registered as active substances for the treatment of various diseases, such as Ralitoline, an antiepileptic, Etozolin, a diuretic, and Piprozolin, a choleretic. The exocyclic C=C double bond in these compounds contains one or two electron-accepting groups at its other end, so that they also belong to the class of the so-called push-pull alkenes. In the case of the nitrogen-unsubstituted molecules, the enamino tautomeric form with the exocyclic double bond is stabilized by the extended electron delocalization arising from the push-pull effect. In the absence of push-pull effect, the imino form would dominate. Therefore, these compounds exhibit properties characteristic for both 4-oxothiazolidine ring and push-pull alkenes. They are also proved to be useful synthetic interamediates for the formation of various mono- and polyheterocycles. The importance of 4-oxothiazolidine derivatives is witnessed by several review articles, the latest published in 2012, mainly dealing with the chemistry and biological activity of various 2-imino, 2-oxo, 2-thioxo and 2-alkyl(aryl)-substituted compounds. The lack of a comprehensive review on 2-alkylidene-4-oxothiazolidines has prompted us to collect the literature covering their synthesis, structure, reactivity and biological activity. Derivatives with two exocyclic C=C double bonds are included, too.
PB  - Bentham Science Publ Ltd, Sharjah
T2  - Current Organic Chemistry
T1  - 4-Oxothiazolidines with Exocyclic C=C Double Bond(s): Synthesis, Structure, Reactions and Biological Activity
VL  - 18
IS  - 9
SP  - 1108
EP  - 1148
DO  - 10.2174/138527281809140624120436
ER  - 
@article{
author = "Stojanović, Milovan and Džambaski, Zdravko and Bondžić, Bojan and Aleksić, Jovana and Baranac-Stojanović, Marija",
year = "2014",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/1810",
abstract = "4-Oxothiazolidine core, owing to the wide range of pharmacological activities exhibited by its derivatives, has been recognized as an important structural motif in biologically active compounds. A subclass constitutes 4-oxothiazolidines with an exocyclic C=C double bond at the C(2)-position. Some of these derivatives are registered as active substances for the treatment of various diseases, such as Ralitoline, an antiepileptic, Etozolin, a diuretic, and Piprozolin, a choleretic. The exocyclic C=C double bond in these compounds contains one or two electron-accepting groups at its other end, so that they also belong to the class of the so-called push-pull alkenes. In the case of the nitrogen-unsubstituted molecules, the enamino tautomeric form with the exocyclic double bond is stabilized by the extended electron delocalization arising from the push-pull effect. In the absence of push-pull effect, the imino form would dominate. Therefore, these compounds exhibit properties characteristic for both 4-oxothiazolidine ring and push-pull alkenes. They are also proved to be useful synthetic interamediates for the formation of various mono- and polyheterocycles. The importance of 4-oxothiazolidine derivatives is witnessed by several review articles, the latest published in 2012, mainly dealing with the chemistry and biological activity of various 2-imino, 2-oxo, 2-thioxo and 2-alkyl(aryl)-substituted compounds. The lack of a comprehensive review on 2-alkylidene-4-oxothiazolidines has prompted us to collect the literature covering their synthesis, structure, reactivity and biological activity. Derivatives with two exocyclic C=C double bonds are included, too.",
publisher = "Bentham Science Publ Ltd, Sharjah",
journal = "Current Organic Chemistry",
title = "4-Oxothiazolidines with Exocyclic C=C Double Bond(s): Synthesis, Structure, Reactions and Biological Activity",
volume = "18",
number = "9",
pages = "1108-1148",
doi = "10.2174/138527281809140624120436"
}
Stojanović, M., Džambaski, Z., Bondžić, B., Aleksić, J.,& Baranac-Stojanović, M. (2014). 4-Oxothiazolidines with Exocyclic C=C Double Bond(s): Synthesis, Structure, Reactions and Biological Activity.
Current Organic Chemistry
Bentham Science Publ Ltd, Sharjah., 18(9), 1108-1148.
https://doi.org/10.2174/138527281809140624120436
Stojanović M, Džambaski Z, Bondžić B, Aleksić J, Baranac-Stojanović M. 4-Oxothiazolidines with Exocyclic C=C Double Bond(s): Synthesis, Structure, Reactions and Biological Activity. Current Organic Chemistry. 2014;18(9):1108-1148
Stojanović Milovan, Džambaski Zdravko, Bondžić Bojan, Aleksić Jovana, Baranac-Stojanović Marija, "4-Oxothiazolidines with Exocyclic C=C Double Bond(s): Synthesis, Structure, Reactions and Biological Activity" Current Organic Chemistry, 18, no. 9 (2014):1108-1148,
https://doi.org/10.2174/138527281809140624120436 .
10
9
9

Supplementary data for article: Baranac-Stojanović, M.; Stojanović, M. Substituent Effects on Cyclic Electron Delocalization in Symmetric B- and N- Trisubstituted Borazine Derivatives. RSC Advances 2013, 3 (46), 24108–24117. https://doi.org/10.1039/c3ra44189j

Baranac-Stojanović, Marija; Stojanović, Milovan

(Royal Soc Chemistry, Cambridge, 2013)

TY  - BOOK
AU  - Baranac-Stojanović, Marija
AU  - Stojanović, Milovan
PY  - 2013
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3526
PB  - Royal Soc Chemistry, Cambridge
T2  - RSC Advances
T1  - Supplementary data for article: Baranac-Stojanović, M.; Stojanović, M. Substituent Effects on Cyclic Electron Delocalization in Symmetric B- and N- Trisubstituted Borazine Derivatives. RSC Advances 2013, 3 (46), 24108–24117. https://doi.org/10.1039/c3ra44189j
ER  - 
@book{
author = "Baranac-Stojanović, Marija and Stojanović, Milovan",
year = "2013",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3526",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "RSC Advances",
title = "Supplementary data for article: Baranac-Stojanović, M.; Stojanović, M. Substituent Effects on Cyclic Electron Delocalization in Symmetric B- and N- Trisubstituted Borazine Derivatives. RSC Advances 2013, 3 (46), 24108–24117. https://doi.org/10.1039/c3ra44189j"
}
Baranac-Stojanović, M.,& Stojanović, M. (2013). Supplementary data for article: Baranac-Stojanović, M.; Stojanović, M. Substituent Effects on Cyclic Electron Delocalization in Symmetric B- and N- Trisubstituted Borazine Derivatives. RSC Advances 2013, 3 (46), 24108–24117. https://doi.org/10.1039/c3ra44189j.
RSC Advances
Royal Soc Chemistry, Cambridge..
Baranac-Stojanović M, Stojanović M. Supplementary data for article: Baranac-Stojanović, M.; Stojanović, M. Substituent Effects on Cyclic Electron Delocalization in Symmetric B- and N- Trisubstituted Borazine Derivatives. RSC Advances 2013, 3 (46), 24108–24117. https://doi.org/10.1039/c3ra44189j. RSC Advances. 2013;
Baranac-Stojanović Marija, Stojanović Milovan, "Supplementary data for article: Baranac-Stojanović, M.; Stojanović, M. Substituent Effects on Cyclic Electron Delocalization in Symmetric B- and N- Trisubstituted Borazine Derivatives. RSC Advances 2013, 3 (46), 24108–24117. https://doi.org/10.1039/c3ra44189j" RSC Advances (2013)