Journal of the American Chemical Society · 1951 · 41 citations · 0 references
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.