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Relation between the substituent effect and aromaticity. Part II. The case of meta ‐ and para ‐homodisubstituted benzene derivatives
Author(s) -
Krygowski Tadeusz M.,
Dobrowolski Michal A.,
Zborowski Krzysztof,
Cyrański Michal K.
Publication year - 2006
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.1039
Subject(s) - chemistry , substituent , benzene , aromaticity , delocalized electron , electron delocalization , benzene derivatives , computational chemistry , medicinal chemistry , organic chemistry , molecule , chemical synthesis , biochemistry , in vitro
Thirty‐two mono‐ and homodisubstituted benzene derivatives ( meta and para isomers) were optimized at B3LYP/6‐311+G** level of theory. The descriptors of cyclic π‐electron delocalization: aromatic stabilization energies (ASE), substituent effects stabilization energies (SESE), NICS and HOMA values were estimated for those systems. Generally, for monosubstituted systems the electron accepting substituents either stabilize the systems or weakly destabilize them. In contrast, the electron donating substituents destabilize the systems in all cases. The π‐electron stabilization/destabilization effects for para ‐di‐homosubstituted benzene derivatives are much stronger than those for the meta analogs. Copyright © 2006 John Wiley & Sons, Ltd.