Aromatic nucleophilic replacement. Part XIV. The mode of transmission of the inductive effect in the benzene ring and the relative activating power of the +NMe2O–, +NMe3, and NO2 groups in aromatic nucleophilic replacement reactions

Abstract

The Arrhenius parameters for the reactions of 3-fluoro-4-nitro-, 4-fluoro-3-nitro-, 3-fluoro-5-nitro-, and 2-fluoro-4-nitro-NN-dimethylaniline N-oxides and 4-fluoro-3-nitro-, and 3-fluoro-5-nitro-phenyltrimethylammonium chlorides with methoxide ion in absolute methanol have been determined. The results are consistent with the operation of a small π-inductive effect and give the relative activating sequences m-⁺NMe₃ > m-NO₂ > m-⁺NMe₂O^– and p-NO₂ > p-⁺NMe₃ > p-⁺NMe₂O^– in aromatic nucleophilic replacement reactions.