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Energetic and geometric characteristics of the substituents. Part 1. The case of NO2 and NH2 groups in their mono-substituted derivatives of simple benzenoid hydrocarbons

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cris.lastimport.scopus2024-02-12T20:00:18Z
dc.abstract.enSimple polycyclic aromatic hydrocarbons, substituted by strongly electron-donating (NH2) and withdrawing (NO2) groups, are studied employing density functional theory (DFT) calculations. A new approach to a description of the substituent effect, the energy of substituent, E(X), is proposed and evaluated. It is defined as E(X) = E(R-X)−E(R), where R is the unsubstituted system; X = NH2, NO2. Changes in the energy of the substituents, estimated for the benzene analog, Erel(X), allow the energy of the various substituents to be compared. The obtained values are interpreted through correlations with the geometry of the substituent and the substituted system. We show that Erel(X) is strongly dependent on the proximity of the substitution. Values of Erel(X) are also compared with a substituent descriptor based on atomic charge distribution–charge of the substituent active region, cSAR(X). It has been shown that these two descriptors correlate very well (R2 > 0.99); however, only for linear acenes with similar, “benzene-like” proximity. Moreover, relations between Erel(X) and cSAR(X), the geometry of the substituents, and angle at the ipso carbon atom can be explained by the well-established Bent–Walsh rule.
dc.affiliationUniwersytet Warszawski
dc.contributor.authorSzatyłowicz, Halina
dc.contributor.authorWieczorkiewicz, Paweł A.
dc.contributor.authorKrygowski, Tadeusz
dc.date.accessioned2024-01-24T22:47:41Z
dc.date.available2024-01-24T22:47:41Z
dc.date.issued2021
dc.description.financePublikacja bezkosztowa
dc.description.number3
dc.description.volume32
dc.identifier.doi10.1007/S11224-021-01754-6
dc.identifier.issn1040-0400
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/106172
dc.identifier.weblinkhttps://link.springer.com/article/10.1007/s11224-021-01754-6
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofStructural Chemistry
dc.relation.pages915-923
dc.rightsClosedAccess
dc.sciencecloudnosend
dc.subject.enSubstituent effect . Polycyclic aromatic hydrocarbons . geometry . Substituent energy . Bent–Walsh rule
dc.titleEnergetic and geometric characteristics of the substituents. Part 1. The case of NO2 and NH2 groups in their mono-substituted derivatives of simple benzenoid hydrocarbons
dc.typeJournalArticle
dspace.entity.typePublication