Journal of the American Chemical Society

The aminolysis of N-hydroxysuccinimide esters. A structure-reactivity study

GW Cline, SB Hanna

Index: Cline, Gary W.; Hanna, Samir B. Journal of the American Chemical Society, 1987 , vol. 109, # 10 p. 3087 - 3091

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Citation Number: 69

Abstract

Abstract: Twelve amines, which vary substantially in basicity and in steric environment around N, have been allowed to compete-in anhydrous dioxane solution-in the aminolysis of the N-hydroxysuccinimide esters of unsubstituted, p-OCH,, p-NO,, and 3, 5-(NO2)* benzoic acids. The amines, which encompass a basicity range of 6.5 pK units, display a 10000-fold variation in reactivity in their reaction with the p-NO2 ester. For the sterically unhindered ...