Abstract
The density functional theory B3LYP/6-31G(d, p) method is employed to study the mechanism of aminolysis reaction of p-substituted phenyl acetates (CH 3C(O)OC 6H 4X, X = H, NH 2, and NO 2) with ammonia in the gas phase. Two reaction pathways are considered: the concerted process and the stepwise pathway through neutral intermediates. The substituent effects of the leaving groups on the reactivity of phenyl acetates are discussed. The solvent effect of acetonitrile on the title reaction is also assessed by the polarizable continuum model (CPCM model) at B3LYP/6-31++G(d, p) level of theory. The calculated results show that the activation barriers of the concerted pathways are lower than those of the rate-controlling steps of the stepwise processes for all the three aminolysis reactions. This aminolysis of phenyl acetates is more favorable for X = NO 2 than for X = H and NH 2 in the gas phase and in acetonitrile.
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