Приказ основних података о документу

dc.creatorStojanović, Milovan
dc.creatorBaranac-Stojanović, Marija
dc.date.accessioned2019-01-30T17:50:50Z
dc.date.available2019-01-30T17:50:50Z
dc.date.issued2016
dc.identifier.issn0022-3263
dc.identifier.urihttps://cer.ihtm.bg.ac.rs/handle/123456789/1974
dc.description.abstractSubstitution 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.en
dc.publisherAmerican Chemical Society (ACS)
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172020/RS//
dc.rightsrestrictedAccess
dc.sourceJournal of Organic Chemistry
dc.titleAromaticity of Diazaborines and Their Protonated Formsen
dc.typearticle
dc.rights.licenseARR
dcterms.abstractБаранац-Стојановиц, Марија; Стојановић, Милован;
dc.citation.volume81
dc.citation.issue1
dc.citation.spage197
dc.citation.epage205
dc.citation.other81(1): 197-205
dc.citation.rankM21
dc.identifier.pmid26625099
dc.identifier.doi10.1021/acs.joc.5b02499
dc.identifier.scopus2-s2.0-84953403666
dc.identifier.wos000367701900021
dc.type.versionpublishedVersion


Документи

Thumbnail

Овај документ се појављује у следећим колекцијама

Приказ основних података о документу