Catalysis of the methoxyaminolysis of phenyl acetate by a preassociation mechanism with a solvent isotope effect maximum

MM Cox, WP Jencks

Index: Cox, Michael M.; Jencks, William P. Journal of the American Chemical Society, 1981 , vol. 103, # 3 p. 572 - 580

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Citation Number: 49

Abstract

Abstract: General-acid catalysis of the reaction of methoxyamine with phenyl acetate by the proton, carboxylic acids, and ammonium ions follows a nonlinear Bransted curve. This curve agrees quantitatively with the behavior expected for the enforced preassociation mechanism of catalysis that was predicted for this reaction. The stronger acids, including the proton, follow a Bransted slope of a= 0.16 that represents rate-limiting amine attack assisted by ...