4-Electron B-N Monocycles: Stability and (Anti)aromaticity
Само за регистроване кориснике
2017
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
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.
Кључне речи:
Aromaticity / Bond theory / Conjugation / Density functional calculations / HeterocyclesИзвор:
European Journal of Organic Chemistry, 2017, 34, 5163-5169Издавач:
- Wiley-V C H Verlag Gmbh, Weinheim
Финансирање / пројекти:
- Експериментална и теоријска проучавања реактивности и биолошка активност стереодефинисаних тиазолидина и синтетичких аналога (RS-MESTD-Basic Research (BR or ON)-172020)
Напомена:
- 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
Колекције
Институција/група
Hemijski fakultet / Faculty of ChemistryTY - 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 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" }
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
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 .
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 . .