Kinetics and mechanism of hydrolysis of acetamides in metal-ion redox systems

Summary The hydrolysis ofN-methylacetamide andN,N-dimenthylacetamide in the presence of cobalt(III) and cerium(IV) has been studied in perchloric acid in the range 10–50° C. The reduction of metal ions and the hydrolysis of amides are very slow processes. However, it appears that reduction of metal ion is coupled with the hydrolysis of amides in such a way as to give enhanced rates for the two processes. The reaction requires one mole of the metal ion for one mole of amide. The rate is proportional to the acid concentration and is independent of ionic strength. Activation parameters have been calculated and reaction mechanisms proposed.