Analysis of Stability and (Anti)aromaticity of BN-Dibenzo[a,e]pentalenes
Само за регистроване кориснике
2018
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
Relatively scarce literature data on BN/CC isosterism in 4nπ-electronic systems have prompted us to investigate theoretically the influence of BN pair position within the central butadiene fragment of dibenzo[a,e]pentalene on two fundamental molecular properties: stability and (anti)aromaticity. It was found that stability and aromaticity follow the same trend only for BN-orientational isomers. The source of different stability of other isomers was examined first by an analysis of bond types and their dissociation energies and then by isomerization energy decomposition analysis and was explained in terms of classical electrostatic interactions, quantum-mechanical orbital interactions, structural changes and electronic changes (transition from charge-separated π-system to the neutral one). (Anti)aromaticity was investigated by using three kinds of indices, HOMA, FLUπ, and NICS(1)zz, which indicated that delocalization at the central pentalene motif is almost unaffected by various BN arr...angements, molecular perimeter is slightly affected, while the most affected subunits are five-membered rings and benzene-fused five-membered rings containing only one heteroatom.
Кључне речи:
Boron / Density functional calculations / Electronic structure / Fused-ring systems / NitrogenИзвор:
European Journal of Organic Chemistry, 2018, 2018, 45, 6230-6240Издавач:
- Wiley-VCH Verlag
Финансирање / пројекти:
Напомена:
- Supplementary information: https://cer.ihtm.bg.ac.rs/handle/123456789/4477
Повезане информације:
- Повезани садржај
https://cer.ihtm.bg.ac.rs/handle/123456789/4477
DOI: 10.1002/ejoc.201801047
ISSN: 1434-193X
WoS: 000456385200006
Scopus: 2-s2.0-85056670746
Институција/група
IHTMTY - JOUR AU - Stojanović, Milovan AU - Baranac-Stojanović, Marija PY - 2018 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/2386 AB - Relatively scarce literature data on BN/CC isosterism in 4nπ-electronic systems have prompted us to investigate theoretically the influence of BN pair position within the central butadiene fragment of dibenzo[a,e]pentalene on two fundamental molecular properties: stability and (anti)aromaticity. It was found that stability and aromaticity follow the same trend only for BN-orientational isomers. The source of different stability of other isomers was examined first by an analysis of bond types and their dissociation energies and then by isomerization energy decomposition analysis and was explained in terms of classical electrostatic interactions, quantum-mechanical orbital interactions, structural changes and electronic changes (transition from charge-separated π-system to the neutral one). (Anti)aromaticity was investigated by using three kinds of indices, HOMA, FLUπ, and NICS(1)zz, which indicated that delocalization at the central pentalene motif is almost unaffected by various BN arrangements, molecular perimeter is slightly affected, while the most affected subunits are five-membered rings and benzene-fused five-membered rings containing only one heteroatom. PB - Wiley-VCH Verlag T2 - European Journal of Organic Chemistry T1 - Analysis of Stability and (Anti)aromaticity of BN-Dibenzo[a,e]pentalenes VL - 2018 IS - 45 SP - 6230 EP - 6240 DO - 10.1002/ejoc.201801047 ER -
@article{ author = "Stojanović, Milovan and Baranac-Stojanović, Marija", year = "2018", abstract = "Relatively scarce literature data on BN/CC isosterism in 4nπ-electronic systems have prompted us to investigate theoretically the influence of BN pair position within the central butadiene fragment of dibenzo[a,e]pentalene on two fundamental molecular properties: stability and (anti)aromaticity. It was found that stability and aromaticity follow the same trend only for BN-orientational isomers. The source of different stability of other isomers was examined first by an analysis of bond types and their dissociation energies and then by isomerization energy decomposition analysis and was explained in terms of classical electrostatic interactions, quantum-mechanical orbital interactions, structural changes and electronic changes (transition from charge-separated π-system to the neutral one). (Anti)aromaticity was investigated by using three kinds of indices, HOMA, FLUπ, and NICS(1)zz, which indicated that delocalization at the central pentalene motif is almost unaffected by various BN arrangements, molecular perimeter is slightly affected, while the most affected subunits are five-membered rings and benzene-fused five-membered rings containing only one heteroatom.", publisher = "Wiley-VCH Verlag", journal = "European Journal of Organic Chemistry", title = "Analysis of Stability and (Anti)aromaticity of BN-Dibenzo[a,e]pentalenes", volume = "2018", number = "45", pages = "6230-6240", doi = "10.1002/ejoc.201801047" }
Stojanović, M.,& Baranac-Stojanović, M.. (2018). Analysis of Stability and (Anti)aromaticity of BN-Dibenzo[a,e]pentalenes. in European Journal of Organic Chemistry Wiley-VCH Verlag., 2018(45), 6230-6240. https://doi.org/10.1002/ejoc.201801047
Stojanović M, Baranac-Stojanović M. Analysis of Stability and (Anti)aromaticity of BN-Dibenzo[a,e]pentalenes. in European Journal of Organic Chemistry. 2018;2018(45):6230-6240. doi:10.1002/ejoc.201801047 .
Stojanović, Milovan, Baranac-Stojanović, Marija, "Analysis of Stability and (Anti)aromaticity of BN-Dibenzo[a,e]pentalenes" in European Journal of Organic Chemistry, 2018, no. 45 (2018):6230-6240, https://doi.org/10.1002/ejoc.201801047 . .