pH optimization of nucleophilic reactions in water

JF King, R Rathore, JYL Lam, ZR Guo…

Index: King; Rathore; Lam; Guo; Klassen Journal of the American Chemical Society, 1992 , vol. 114, # 8 p. 3028 - 3033

Full Text: HTML

Citation Number: 55

Abstract

Abstract: We present a way of prescribing the pH for a reaction so as to obtain either (a) maximum yield in competition with hydrolysis or (b) selective reaction at either of two sites in such nucleophile-electrophile reactions as C-alkylation of acidic ketones and the acylation and sulfonylation of amines. First, we derive the following general equation for pH,,, the pH giving the highest yield of the product (P) of the reaction of a nucleophile (Nu) with a ...