Abstract
N-(2,6-Dinitro-4-trifluoromethylphenyl)aniline derivatives were prepared by anilino-dechlorination of 4-chloro-3, 5-dinitrobenzotrifluoride. IR, UV and H-1 NMR studies suggested an intramolecular hydrogen bond between the amino hydrogen and one o-nitro group. An addition-elimination mechanism was suggested based on the second-order kinetics and the dependence of rates on the nature and the position of the substituent in the aniline ring, as well as the high negative values of rho (-3.14, -3.16, -3.01). Such values indicate a positive charge on the aniline nitrogen in the transition state and that the rate is affected by the polar effect of the substituent. The beta value (0.85 at 30 degrees C) indicates an appreciable degree of bond formation in the transition state.