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Energetic and Geometric Characteristics of the Substituents: Part 2: The Case of NO2, Cl, and NH2 Groups in Their Mono-Substituted Derivatives of Simple Nitrogen Heterocycles

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dc.abstract.en<jats:p>Variously substituted N-heterocyclic compounds are widespread across bio- and medicinal chemistry. The work aims to computationally evaluate the influence of the type of N-heterocyclic compound and the substitution position on the properties of three model substituents: NO2, Cl, and NH2. For this reason, the energetic descriptor of global substituent effect (Erel), geometry of substituents, and electronic descriptors (cSAR, pEDA, sEDA) are considered, and interdependences between these characteristics are discussed. Furthermore, the existence of an endocyclic N atom may induce proximity effects specific for a given substituent. Therefore, various quantum chemistry methods are used to assess them: the quantum theory of atoms in molecules (QTAIM), analysis of non-covalent interactions using reduced density gradient (RDG) function, and electrostatic potential maps (ESP). The study shows that the energetic effect associated with the substitution is highly dependent on the number and position of N atoms in the heterocyclic ring. Moreover, this effect due to interaction with more than one endo N atom (e.g., in pyrimidines) can be assessed with reasonable accuracy by adding the effects calculated for interactions with one endo N atom in substituted pyridines. Finally, all possible cases of proximity interactions for the NO2, Cl, and NH2 groups are thoroughly discussed.</jats:p>
dc.affiliationUniwersytet Warszawski
dc.contributor.authorWieczorkiewicz, Paweł A.
dc.contributor.authorSzatyłowicz, Halina
dc.contributor.authorKrygowski, Tadeusz
dc.date.accessioned2024-01-24T22:47:42Z
dc.date.available2024-01-24T22:47:42Z
dc.date.copyright2021-10-29
dc.date.issued2021
dc.description.accesstimeAT_PUBLICATION
dc.description.financePublikacja bezkosztowa
dc.description.number21
dc.description.versionFINAL_PUBLISHED
dc.description.volume26
dc.identifier.doi10.3390/MOLECULES26216543
dc.identifier.issn1420-3049
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/106173
dc.identifier.weblinkhttps://www.mdpi.com/1420-3049/26/21/6543
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofMolecules
dc.relation.pages1-18
dc.rightsCC-BY
dc.sciencecloudnosend
dc.subject.ensubstituent effect
dc.subject.enheterocyclic compounds
dc.subject.enpyridine
dc.subject.ensubstituent energy
dc.titleEnergetic and Geometric Characteristics of the Substituents: Part 2: The Case of NO2, Cl, and NH2 Groups in Their Mono-Substituted Derivatives of Simple Nitrogen Heterocycles
dc.typeJournalArticle
dspace.entity.typePublication