Abstract: Hydronium and hydroxide ion catalyzed amide hydrogen exchange rate constants have been measured for a series of acyl-substituted amides and several rebated compounds. Substituents which exert electron-withdrawing polar effects were found to increase the hydroxide ion rate constant OH) by more than lo3 (PI=+ 0.87) and to decrease the hydronium ion (kH) catalyzed rate constant, for a more limited series, by greater than ...
[Challis, Brian C.; Iley, James N. Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1987 , p. 1489 - 1494]