Kinetics of aminolysis of 2,4-dinitrophenyl acetate

Abstract

757-760The second order rate constants for the reaction of 2,4-dinitrophenyl acetate with aniline and p- and o-substituted anilines have been reported in 10% acetonitrile-90% water (v/v) mixture at 25°, 30°, 35° and 40°C. In the reaction of p-substituted anilines, electron-releasing groups facilitate the reaction while electron-withdrawing groups retard it. The ρ-value is evaluated to be - 2.33 ± 0.16. The Bronsted plot is also linear with βN = 0.792 ± 0.027 at 30°C. The S≠ values are all negative as expected for bimolecular nucleophilic substitution reactions. In the case of o-substituted anilines, the rate data have been analysed in terms of electronic and steric effects

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