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Conjugation and aromaticity of macrocyclic systems
Author(s) -
Randić Milan,
Henderson Larhee L.,
Stout Roland,
Trinajstić Nenad
Publication year - 1988
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.560340817
Subject(s) - aromaticity , benzene , valence (chemistry) , valence bond theory , conjugated system , computational chemistry , molecule , chemistry , ring (chemistry) , hückel method , chemical physics , molecular orbital , organic chemistry , polymer
Using a graph theoretical approach we have analyzed the aromatic stability of macrocylic systems having ten and fewer fused benzene rings. The approach requires construction and examination of Kekule valence structures of the macrocyclic systems considered. The Kekule valence structures for a molecule were systematically derived and the conjugated circuits in the individual Kekule formulas were enumerated subsequently. The counting results is the expression for molecular resonance energy, from which relative aromatic stabilities can be established. We report also on molecular local features, including ring benzene characters and Pauling bond orders.