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
Journal of the Chemical Society B: Physical Organic Pub Date: DOI: 10.1039/J29680000238
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.
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Journal Name：Journal of the Chemical Society B: Physical Organic
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CAS no.: 89640-58-4
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