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dc.creatorBaranac-Stojanović, Marija
dc.creatorStojanović, Milovan
dc.creatorAleksić, Jovana
dc.date.accessioned2021-04-07T08:47:19Z
dc.date.available2021-04-07T08:47:19Z
dc.date.issued2021
dc.identifier.issn1369-9261
dc.identifier.urihttp://cherry.chem.bg.ac.rs/handle/123456789/4355
dc.description.abstractAromaticity–antiaromaticity switch upon singlet–triplet transition of some biologically and synthetically important monoheterocycles (heteroatom = N, O, Si, P, and S) derived from benzene, naphthalene and anthracene was studied by employing energetic, magnetic and structural aromaticity criteria, at the density functional theory (DFT) level. The relationship between spin density distribution, (anti)aromaticity and singlet–triplet energy gaps, in the studied molecules, was found. In general, spin delocalization results in antiaromaticity, spin density localization to one ring in bi- and tricycles localizes antiaromaticity and spin localization on a heteroatom reduces global and local antiaromaticity. The latter reaches nonaromaticity in the case of silicon atoms which have larger orbitals and show more tendency to accept unpaired electrons. Spin density localization in bi- and tricycles allows benzene subunit(s) to develop local aromaticity, which, when combined with nonaromatic silacycle and weak global antiaromaticity, results in overall triplet state weak aromaticity. The singlet–triplet energy gaps decrease with a decrease in the triplet state antiaromaticity and are the lowest for silicon-containing compounds.
dc.languageen
dc.publisherRoyal Society of Chemistry
dc.relationinfo:eu-repo/grantAgreement/MESTD/inst-2020/200168/RS//
dc.relation.isversionofhttps://doi.org/10.1039/D1NJ00207D
dc.relation.isreferencedbyhttps://cherry.chem.bg.ac.rs/handle/123456789/4356
dc.rightsrestrictedAccess
dc.sourceNew Journal of Chemistry
dc.titleTriplet state (anti)aromaticity of some monoheterocyclic analogues of benzene, naphthalene and anthracene
dc.typearticleen
dc.rights.licenseARR
dcterms.abstractСтојановић, Милован; Баранац-Стојановић, Марија; Aлексић, Јована;
dc.citation.volume45
dc.citation.issue11
dc.citation.spage5060
dc.citation.epage5074
dc.identifier.doi10.1039/D1NJ00207D
dc.description.otherSupplementary material: [https://cherry.chem.bg.ac.rs/handle/123456789/4356]
dc.type.versionpublishedVersion
dc.identifier.scopus2-s2.0-85102960034


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