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How far the substituent effects in disubstituted cyclohexa-1,3-diene derivatives differ from those in bicyclo[2.2.2]octane and benzene?

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cris.lastimport.scopus2024-02-12T20:18:22Z
dc.abstract.enSubstituents effects in cyclic diene derivatives are studied using quantum chemical modeling and compared to the corresponding effects in aromatic (benzene) and fully saturated (bicyclo[2.2.2]octane) compounds. In particular, electronic properties of the fixed group Y in a series of 3- and 4-X-substituted cyclohexa-1,3-diene-Y derivatives (where Y = NO2, COOH, COO− OH, O−, NH2, and X = NMe2, NH2, OH, OMe, Me, H, F, Cl, CF3, CN, CHO, COMe, CONH2, COOH, NO2, NO) are examined using the B3LYP/6-311++G(d,p) method. For this purpose, quantum chemistry models of the substituent effect: cSAR (charge of the substituent active region) and SESE (substituent effect stabilization energy) as well as traditional Hammett’s substituent constants (σ) and their inductive (F) and resonance (R) components are used. π-electron delocalization of the transmitting moiety (butadiene fragment of the CHD) is described by the HOMA index. This comparative study reveals interplay between inductive and resonance contributions to the substituent effect.
dc.affiliationUniwersytet Warszawski
dc.contributor.authorSiodła, Tomasz
dc.contributor.authorSzatylowicz, Halina
dc.contributor.authorJezuita, Anna
dc.contributor.authorShahamirian, Mozhgan
dc.contributor.authorVaraksin, Konstantin S.
dc.contributor.authorEjsmont, Krzysztof
dc.contributor.authorKrygowski, Tadeusz
dc.date.accessioned2024-01-25T03:29:50Z
dc.date.available2024-01-25T03:29:50Z
dc.date.copyright2018-06-09
dc.date.issued2018
dc.description.accesstimeAT_PUBLICATION
dc.description.financeNie dotyczy
dc.description.number4
dc.description.versionFINAL_PUBLISHED
dc.description.volume29
dc.identifier.doi10.1007/S11224-018-1113-5
dc.identifier.issn1040-0400
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/108659
dc.identifier.weblinkhttps://link.springer.com/article/10.1007/s11224-018-1113-5
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofStructural Chemistry
dc.relation.pages1201-1212
dc.rightsCC-BY
dc.sciencecloudnosend
dc.subject.ensubstituent effects
dc.subject.enelectronic structure
dc.subject.enmolecular modeling
dc.subject.ensubstituent effect stabilization energy
dc.subject.encharge of the substituent active region
dc.titleHow far the substituent effects in disubstituted cyclohexa-1,3-diene derivatives differ from those in bicyclo[2.2.2]octane and benzene?
dc.typeJournalArticle
dspace.entity.typePublication