Evaluation of Slight Changes in Aromaticity through Electronic and Density Functional Reactivity Theory-Based Descriptors

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dc.contributor.authorBáez Grez, Rodrigo
dc.contributor.authorPino Rios, Ricardo
dc.date.accessioned2023-12-04T13:57:11Z
dc.date.available2023-12-04T13:57:11Z
dc.date.issued2022-06-28
dc.descriptionIndexación: Scopus.es
dc.description.abstractAromaticity is a useful tool to rationalize the structure, stability, and reactivity in several compounds. Although aromaticity is not directly an observable, it is well accepted that electronic delocalization around the molecular ring is a key stabilizing feature of aromatic compounds. This contribution presents a systematic evaluation of the capability of delocalization and reactivity criteria to describe aromaticity in a set of fluorinated benzenes. The aromaticity indices are compared with quantities obtained from the magnetic criteria of aromaticity, i.e., the strength of the ring current induced by an external magnetic field and the popular NICSzz(1) index. In this evaluation, the indices based on delocalization criteria used are aromatic fluctuation index (FLU), para-delocalization index (PDI), PDIπ, and the multicenter delocalization index (MCI). In addition, indices based on the bifurcation values of scalar functions are derived from electron density such as electron localization function (the πcontribution, ELFπ) and the πcontribution of the localized orbital locator (LOLπ). Furthermore, reactivity indices based on chemical reactivity and the information-theoretic (reactivity) approach are para-linear response (PLR), Shannon entropy, Fisher information, and Ghosh-Berkowitz-Parr (GBP) entropy. The results obtained show that the delocalization-based indicators present a high sensitivity to slight changes in aromaticity and that the reactivity criterion can be considered as a complementary tool for the study of this phenomenon, even when these changes are minimal. These results encourage the use of multiple indicators for a complete understanding of aromaticity in various chemical compounds. © 2022 The Authors. Published by American Chemical Society.es
dc.description.urihttps://pubs-acs-org.recursosbiblioteca.unab.cl/doi/10.1021/acsomega.2c02291#
dc.identifier.citationACS Omega, Volume 7, Issue 25, Pages 21939 - 21945, 28 June 2022es
dc.identifier.doi10.1021/acsomega.2c02291
dc.identifier.issn2470-1343
dc.identifier.urihttps://repositorio.unab.cl/xmlui/handle/ria/54364
dc.language.isoenes
dc.publisherAmerican Chemical Societyes
dc.rights.licenseCC BY-NC-ND 4.0 DEED Attribution-NonCommercial-NoDerivs 4.0 International
dc.rights.urihttps://creativecommons.org/licenses/by-nc-nd/4.0/
dc.subjectAromaticityes
dc.subjectAromatic Compoundes
dc.subjectDelocalizationes
dc.titleEvaluation of Slight Changes in Aromaticity through Electronic and Density Functional Reactivity Theory-Based Descriptorses
dc.typeArtículoes
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