1972•Canadian Journal of ChemistryRequires access
Kinetic Evidence for Predominant Oxygen Protonation of Amides
Clinton R. Smith, Keith Yates
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Abstract
Comparison of rate data for the acid-catalyzed hydrolysis of amides, and model compounds for O- and N-protonated amides, provides strong evidence that amides protonate predominantly on oxygen in dilute as well as in concentrated aqueous acids, contrary to a recent proposal that the protonation sites are different in the two media.