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4-Electron B-N Monocycles: Stability and (Anti)aromaticity

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2017
Authors
Baranac-Stojanović, Marija
Article (Published version)
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Abstract
This is a theoretical (DFT) study of the impact of electronic structural changes, induced by B-N/C-C isosterism, on two basic properties of 4-electron antiaromatic system, that is, stability and antiaromaticity. The main driving force for the nonplanarity of B2N2 rings is electrostatic energy, and that for a ring with one B-N unit is the relief of Pauli repulsion. The charge-separation instability, inherent for a 1,3-B,N relationship, turns the ground state of the BCNC system to an aromatic triplet, which is less stable than the isomeric BNCC system, mostly because of larger Pauli interactions. The alternating BNBN connectivity is favoured primarily by orbital interaction energy and, secondarily, by better electrostatic attraction. The C-C B-N substitution weakens the antiaromatic character, except that for a 1,3-B,N relationship, which results in increased antiaromaticity in the closed-shell state relative to that of cyclobutadiene.
Keywords:
Aromaticity / Bond theory / Conjugation / Density functional calculations / Heterocycles
Source:
European Journal of Organic Chemistry, 2017, 34, 5163-5169
Publisher:
  • Wiley-V C H Verlag Gmbh, Weinheim
Funding / projects:
  • Experimental and theoretical study of reactivity and biological activity of stereodefined thiazolidines and their synthetic analogues (RS-172020)
Note:
  • Peer-reviewed manuscript: http://cherry.chem.bg.ac.rs/handle/123456789/3825

DOI: 10.1002/ejoc.201700959

ISSN: 1434-193X

WoS: 000410792200022

Scopus: 2-s2.0-85029513783
[ Google Scholar ]
6
5
URI
https://cherry.chem.bg.ac.rs/handle/123456789/2526
Collections
  • Publikacije
Institution/Community
Hemijski fakultet
TY  - JOUR
AU  - Baranac-Stojanović, Marija
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2526
AB  - This is a theoretical (DFT) study of the impact of electronic structural changes, induced by B-N/C-C isosterism, on two basic properties of 4-electron antiaromatic system, that is, stability and antiaromaticity. The main driving force for the nonplanarity of B2N2 rings is electrostatic energy, and that for a ring with one B-N unit is the relief of Pauli repulsion. The charge-separation instability, inherent for a 1,3-B,N relationship, turns the ground state of the BCNC system to an aromatic triplet, which is less stable than the isomeric BNCC system, mostly because of larger Pauli interactions. The alternating BNBN connectivity is favoured primarily by orbital interaction energy and, secondarily, by better electrostatic attraction. The C-C B-N substitution weakens the antiaromatic character, except that for a 1,3-B,N relationship, which results in increased antiaromaticity in the closed-shell state relative to that of cyclobutadiene.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - European Journal of Organic Chemistry
T1  - 4-Electron B-N Monocycles: Stability and (Anti)aromaticity
IS  - 34
SP  - 5163
EP  - 5169
DO  - 10.1002/ejoc.201700959
UR  - Kon_3342
ER  - 
@article{
author = "Baranac-Stojanović, Marija",
year = "2017",
abstract = "This is a theoretical (DFT) study of the impact of electronic structural changes, induced by B-N/C-C isosterism, on two basic properties of 4-electron antiaromatic system, that is, stability and antiaromaticity. The main driving force for the nonplanarity of B2N2 rings is electrostatic energy, and that for a ring with one B-N unit is the relief of Pauli repulsion. The charge-separation instability, inherent for a 1,3-B,N relationship, turns the ground state of the BCNC system to an aromatic triplet, which is less stable than the isomeric BNCC system, mostly because of larger Pauli interactions. The alternating BNBN connectivity is favoured primarily by orbital interaction energy and, secondarily, by better electrostatic attraction. The C-C B-N substitution weakens the antiaromatic character, except that for a 1,3-B,N relationship, which results in increased antiaromaticity in the closed-shell state relative to that of cyclobutadiene.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "European Journal of Organic Chemistry",
title = "4-Electron B-N Monocycles: Stability and (Anti)aromaticity",
number = "34",
pages = "5163-5169",
doi = "10.1002/ejoc.201700959",
url = "Kon_3342"
}
Baranac-Stojanović, M.. (2017). 4-Electron B-N Monocycles: Stability and (Anti)aromaticity. in European Journal of Organic Chemistry
Wiley-V C H Verlag Gmbh, Weinheim.(34), 5163-5169.
https://doi.org/10.1002/ejoc.201700959
Kon_3342
Baranac-Stojanović M. 4-Electron B-N Monocycles: Stability and (Anti)aromaticity. in European Journal of Organic Chemistry. 2017;(34):5163-5169.
doi:10.1002/ejoc.201700959
Kon_3342 .
Baranac-Stojanović, Marija, "4-Electron B-N Monocycles: Stability and (Anti)aromaticity" in European Journal of Organic Chemistry, no. 34 (2017):5163-5169,
https://doi.org/10.1002/ejoc.201700959 .,
Kon_3342 .

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