dc.creator | Baranac-Stojanović, Marija | |
dc.creator | Stojanović, Milovan | |
dc.creator | Aleksić, Jovana | |
dc.date.accessioned | 2021-04-21T09:33:49Z | |
dc.date.available | 2021-04-21T09:33:49Z | |
dc.date.issued | 2021 | |
dc.identifier.issn | 1144-0546 | |
dc.identifier.issn | 1369-9261 | |
dc.identifier.uri | https://cer.ihtm.bg.ac.rs/handle/123456789/4483 | |
dc.description.abstract | Aromaticity–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. | sr |
dc.language.iso | en | sr |
dc.publisher | Royal Society of Chemistry | sr |
dc.relation | info:eu-repo/grantAgreement/MESTD/inst-2020/200168/RS// | sr |
dc.relation.isreferencedby | https://cer.ihtm.bg.ac.rs/handle/123456789/4484 | |
dc.rights | restrictedAccess | sr |
dc.source | New Journal of Chemistry | sr |
dc.subject | benzene | sr |
dc.subject | naphthalene | sr |
dc.subject | anthracene | sr |
dc.subject | Aromaticity | sr |
dc.subject | Aromatization | sr |
dc.subject | Vehicles | sr |
dc.subject | Silicon compounds | sr |
dc.subject | Spin delocalizations | sr |
dc.subject | Singlet-triplet energy gap | sr |
dc.subject | Spin density distributions | sr |
dc.subject | Density functional theory | sr |
dc.subject | Energy gap | sr |
dc.subject | Naphthalene | sr |
dc.subject | Silicon compounds | sr |
dc.subject | Antiaromaticity | sr |
dc.title | Triplet state (anti)aromaticity of some monoheterocyclic analogues of benzene, naphthalene and anthracene | sr |
dc.type | article | sr |
dc.rights.license | ARR | sr |
dcterms.abstract | Стојановић, Милован; Aлексић, Јована; Баранац-Стојановић, Марија; | |
dc.citation.volume | 45 | |
dc.citation.issue | 11 | |
dc.citation.spage | 5060 | |
dc.citation.epage | 5074 | |
dc.citation.rank | M22~ | |
dc.description.other | Supplementary information: [https://cer.ihtm.bg.ac.rs/handle/123456789/4484] | |
dc.identifier.doi | 10.1039/d1nj00207d | |
dc.identifier.scopus | 2-s2.0-85102960034 | |
dc.identifier.wos | 000631378900016 | |
dc.type.version | publishedVersion | sr |