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Benzenoid rings resonance energies and local aromaticity of benzenoid hydrocarbons
Author(s) -
Randić Milan
Publication year - 2019
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.25760
Subject(s) - aromaticity , ring (chemistry) , benzene , chemistry , conjugated system , molecule , resonance (particle physics) , computational chemistry , physics , organic chemistry , atomic physics , polymer
In this article, we consider partitioning of the analytical expression for resonance energy (RE) in smaller benzenoid hydrocarbons, to individual benzenoid rings of polycyclic molecules. The analytical expression for molecular RE, available since 1976, is given by the count of all linearly independent conjugated circuit in all Kekulé structures in a molecule. Analytical expression for local ring RE (RRE) is given by counting all linearly independent conjugated circuits involving single benzenoid ring in all Kekulé structures, which when added, gives the molecular RE. If for benzene ring the RRE is taken to be 1.000, rings in polycyclic benzenoid hydrocarbons have their ring RRE, which give the degree of their local aromaticity, smaller than 1.000. The difference to 1.000 is a measure of the similarity of a ring to benzene in this one‐dimensional (1‐D) representation of local aromaticities of benzenoid hydrocarbons. The plot of RRE against the distance of the same ring from benzene in the Local Aromaticity Map, in which benzenoid rings are characterized ring bond orders and average variations of adjacent CC bonds, shows linear correlation (with r = 0.91), reducing the local aromaticity in benzenoid hydrocarbons to 1‐D molecular property. © 2018 Wiley Periodicals, Inc.