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Is coronene better described by C lar's aromatic π‐sextet model or by the AdNDP representation?
Author(s) -
Kumar Anand,
Duran Miquel,
Solà Miquel
Publication year - 2017
Publication title -
journal of computational chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.907
H-Index - 188
eISSN - 1096-987X
pISSN - 0192-8651
DOI - 10.1002/jcc.24801
Subject(s) - coronene , aromaticity , naphthalene , chemistry , phenanthrene , density functional theory , representation (politics) , computational chemistry , molecule , chemical physics , organic chemistry , politics , political science , law
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. © 2017 Wiley Periodicals, Inc.