Nucleophilic Attack vs. General Base Assisted Hydrolysis in the Reactions of Acetic Anhydride with Primary and Secondary Amines. pH-Yield Studies in the …
JF King, ZR Guo, DF Klassen
Index: King, James F.; Guo, Zhen Rong; Klassen, Darryl F. Journal of Organic Chemistry, 1994 , vol. 59, # 5 p. 1095 - 1101
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Citation Number: 17
Abstract
The reaction of a set of primary and secondary amines with acetic anhydride in water at 25 OC gave variable yields of the N-substituted acetamide in seven of the eight amines studied. The yield of the amide as a function of pH revealed the incursion in most cases of a general base assisted hydrolysis of the acetic anhydride by the amine. From the pKis of the amines and k, and ko~ for acetic anhydride (the specific rates for the reaction of the anhydride with ...
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