The Electrical Effect of the Trimethylammonium [-N(CH_3)_3^⊕] Group

Abstract

A study has been made of the reactivities of a series of anilines and benzoic acids substituted in the meta- and para-positions with trimethylammonium [-N(CH_3)_3^⊕] groups. The experimental results offer no support for preferential relay of the inductive effect of a substituent group to the ortho- and para-positions of a benzene ring as postulated by Robinson, Ingold and others. The strong meta-orienting influence of the -N(CH_3)_3^⊕ in electrophilic aromatic substitution reactions seems best accounted for by the approach of Pfeiffer and Wizinger.

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