An atomic interaction energy approach to the reactivity of the aromatic ring toward electrophilic attack

Abstract

AbstractA procedure of constructing a complete fragment orbital basis set is described in detail. It provides a complete fragment orbital basis for PMO analysis of the atomic interaction energy. Rt values, a ratio of the bonded atomic interaction energy to the nonbonded interaction energy arising from the peripheral atoms of the aromatic rings, indicate a decrease in the reactivity of the aromatic ring toward electrophilic attack in the sequence: pyrrole > imidazole > furan > pyrazine > pyrimidine > aniline > benzene > pyridine > p‐acylaniline > p‐cyanoaniline > p‐nitroaniline > m‐cyanoaniline. © 1995 John Wiley & Sons, Inc.