Abstract
Abstract Proton exchange of N-methyl amides with general acid catalysis in aqueous solution was studied by NMR. Rate coefficients were determined by NMR lineshape analysis of the N-methyl protons. The imidic acid mechanism is favored by amides with electron-withdrawing substituents. Only the imidic acid mechanism is expected to show general acid catalysis, and this mechanism was observed with Brønsted α = 0.16 for the Z proton of N-methylformamide. No general acid catalysis was observed for N-methyl-2-chloroacetamide and N,N′-dimethylmalonamide which exchange protons via the imidic acid mechanism. This result is attributed to their Z conformations.
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