ELECTROCHEMICAL REDUCTION OF BENZAMIDE AND THEIR O-HALO-DERIVATIVES AND P-HALO-DERIVATIVES IN NONAQUEOUS SOLVENTS

The analysis of the polarographic, voltammetric and coulometric result s shows that the overall reduction mechanism of benzamide occurs with the cleavage of the C-N bond. However, the first step of the electroch emical process leads to the formation of a radical anion which undergo es protonation by another benzamide molecule in DMF and DMSO or by the solvent in CH3CN and C2H5OH. Theoretical calculations have been perfo rmed to clarify the mechanism. Halobenzamide reduction involves the C- halogen bond breaking as the first reduction step to give benzamide.