Abstract
PREVIOUS work on acid-catalysed amide hydrolysis has indicated that the reaction is bimolecular: in the rate-determining step the conjugate acid of the amide is attacked by a water molecule1. This conclusion is derived from three types of evidence. It has been shown that in concentrated aqueous acid solutions the rate of hydrolysis of a number of simple amides increases with the proportion of water in the solvent2; that polar substituents in the acyl part of the amide molecule have very little effect on the rate3; and that the rate is substantially diminished by groups, for example, ortho substituents in benzamides, which shield the reaction centre from attack by other molecules3 4.
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References
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DUFFY, J., LEISTEN, J. A New Mechanism for Amide Hydrolysis. Nature 178, 1242–1243 (1956). https://doi.org/10.1038/1781242b0
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DOI: https://doi.org/10.1038/1781242b0
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