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Chemical graph theory and n ‐center electron delocalization indices: A study on polycyclic aromatic hydrocarbons
Author(s) -
Mandado Marcos,
GonzálezMoa María J.,
Mosquera Ricardo A.
Publication year - 2007
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.20647
Subject(s) - electron delocalization , delocalized electron , computational chemistry , graph , polycyclic aromatic hydrocarbon , chemistry , center (category theory) , graph theory , aromaticity , mathematics , combinatorics , organic chemistry , molecule , crystallography
Relations between aromaticity indices derived from chemical graph theory and those based on 6‐center electron delocalization are investigated for a series of polybenzenoid hydrocarbons. Aromatic stabilization obtained by means of the effective scaled electron delocalization is highly correlated to the resonance energy, RE, obtained both from SCF MO calculations and conjugated ring circuits model. Local aromaticity of benzene rings is discussed using two different criteria, in one of them aromaticity is just given by the cyclic π ‐electron conjugation of the ring, whereas terms involving more than one ring are also considered in the other one. Indices derived from chemical graph theory and those obtained from the 6‐center electron delocalization give rise to the same local aromaticity. Moreover, 6‐center electron delocalization provides more quantitative information. © 2007 Wiley Periodicals, Inc. J Comput Chem, 2007