Abstract

An analysis of the mechanism for the effect of substituents and heteroatoms on the direction of electrophilic attack in monosubstituted benzene, furan, thiophene, and pyrrole was carried out within the framework of the Swain-Lupton, Yukawa- Tsuno, and Dewar-Grisdale methods. The variation in the resonance factor is in good accord with the activity series for the heterocycles in electrophilic substitution reactions, while description of the selectivity of electrophilic attack requires consideration of both the resonance and inductive effects of the substituent and of the heteroatom.

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