Reactivity of phenolates in the reaction with p-nitrophenyl acetate
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The kinetics of the reaction of p-nitrophenyl acetate with a series of o- and p-substituted phenolates and benzylamines was studied. In the reaction with the participation of o-aminomethylphenols two forms of phenolates are reactive, and in contrast to the usual phenolates, both are nucleophilic catalysts of the hydrolysis of p-nitrophenyl acetate, due to intramolecular catalysis of the splitting of the acetylated o-aminomethylphenol.
The specific behavior of the zwitterions of o-aminomethylphenols is explained by their ability to undergo a bifunctional reaction with the substrate.
KeywordsAcetate Hydrolysis Phenolate Catalysis Specific Behavior
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