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Is coronene better described by Clar’s aromatic π-sextet model or by the AdNDP representation?

The bonding patterns in coronene are complicated and controversial as denoted by the lack of consensus of how its electronic structure should be described. Among the different proposed descriptions, the two most representative are those generated by Clar’s aromatic π-sextet and adaptative natural density partitioning (AdNDP) models. Quantum-chemical calculations at the density functional theory level are performed to evaluate the model that gives a better representation of coronene. To this end, we analyse the molecular structure of coronene, we estimate the aromaticity of its inner and outer rings using various local aromaticity descriptors, and we assess its chemical reactivity from the study of the Diels–Alder reaction with cyclopentadiene. Results obtained are compared with those computed for naphthalene and phenanthrene. Our conclusion is that Clar’s π-sextet model provides the representation of coronene that better describes the physicochemical behavior of this molecule

© Journal of Computational Chemistry, 2017, vol. 38, núm. 18, p. 1606-1611

Wiley

Author: Kumar, Anand
Duran i Portas, Miquel
Solà i Puig, Miquel
Date: 2017 July 5
Abstract: The bonding patterns in coronene are complicated and controversial as denoted by the lack of consensus of how its electronic structure should be described. Among the different proposed descriptions, the two most representative are those generated by Clar’s aromatic π-sextet and adaptative natural density partitioning (AdNDP) models. Quantum-chemical calculations at the density functional theory level are performed to evaluate the model that gives a better representation of coronene. To this end, we analyse the molecular structure of coronene, we estimate the aromaticity of its inner and outer rings using various local aromaticity descriptors, and we assess its chemical reactivity from the study of the Diels–Alder reaction with cyclopentadiene. Results obtained are compared with those computed for naphthalene and phenanthrene. Our conclusion is that Clar’s π-sextet model provides the representation of coronene that better describes the physicochemical behavior of this molecule
Format: application/pdf
Citation: https://doi.org/10.1002/jcc.24801
ISSN: 0192-8651 (versió paper)
1096-987X (versió electrònica)
Document access: http://hdl.handle.net/10256/14342
Language: eng
Publisher: Wiley
Collection: Reproducció digital del document publicat a: https://doi.org/10.1002/jcc.24801
Articles publicats (D-Q)
Is part of: © Journal of Computational Chemistry, 2017, vol. 38, núm. 18, p. 1606-1611
Rights: Tots els drets reservats
Subject: Aromaticitat (Química)
Aromaticity (Chemistry)
Funcional de densitat, Teoria del
Density functionals
Diels-Alder, Reacció de
Diels-Alder reaction
Title: Is coronene better described by Clar’s aromatic π-sextet model or by the AdNDP representation?
Type: info:eu-repo/semantics/article
Repository: DUGiDocs

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