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The kinetics of general base catalyzed proton exchange in N,N′-dimethylurea and a series of secondary amides were studied. Kinetic data were determined by NMR line-shape analysis. A good linear correlation was observed for nine amides by plotting log kOH for RCONHCH3 vs. pKa of RCOOH. For amides with N–H more acidic than water (pKa < 15.7), general base catalysis is observed, the Brønsted β is unity, and the reaction with hydroxide is diffusion-controlled. It is concluded that general base catalysis is inoperative in proteins or polypeptides.
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Wang et al. (1994) studied this question.
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