Substituent effects on amide hydrogen exchange rates in aqueous solution

RS Molday, RG Kallen

Index: Molday,R.S.; Kallen,R.G. Journal of the American Chemical Society, 1972 , vol. 94, p. 6739 - 6745

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Citation Number: 84

Abstract

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 ...