CER - Central Repository
Institute of Chemistry, Technology and Metallurgy
    • English
    • Српски
    • Српски (Serbia)
  • English 
    • English
    • Serbian (Cyrilic)
    • Serbian (Latin)
  • Login
View Item 
  •   Central Repository
  • IHTM
  • Radovi istraživača / Researchers' publications
  • View Item
  •   Central Repository
  • IHTM
  • Radovi istraživača / Researchers' publications
  • View Item
JavaScript is disabled for your browser. Some features of this site may not work without it.

Analysis of Stability and (Anti)aromaticity of BN-Dibenzo[a,e]pentalenes

Authorized Users Only
2018
Authors
Stojanović, Milovan
Baranac-Stojanović, Marija
Article (Published version)
Metadata
Show full item record
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 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.

Keywords:
Boron / Density functional calculations / Electronic structure / Fused-ring systems / Nitrogen
Source:
European Journal of Organic Chemistry, 2018, 2018, 45, 6230-6240
Publisher:
  • Wiley-VCH Verlag
Projects:
  • Experimental and theoretical study of reactivity and biological activity of stereodefined thiazolidines and their synthetic analogues (RS-172020)

DOI: 10.1002/ejoc.201801047

ISSN: 1434-193X

WoS: 000456385200006

Scopus: 2-s2.0-85056670746
[ Google Scholar ]
1
1
URI
http://cer.ihtm.bg.ac.rs/handle/123456789/2386
Collections
  • Radovi istraživača / Researchers' publications
Institution
IHTM

DSpace software copyright © 2002-2015  DuraSpace
About CeR – Central Repository | Send Feedback

OpenAIRERCUB
 

 

All of DSpaceInstitutionsAuthorsTitlesSubjectsThis institutionAuthorsTitlesSubjects

Statistics

View Usage Statistics

DSpace software copyright © 2002-2015  DuraSpace
About CeR – Central Repository | Send Feedback

OpenAIRERCUB