The analysis of the polarographic, voltammetric and coulometric results shows that the overall reduction mechanism of benzamide occurs with the cleavage of the C-N bond. However, the first step of the electrochemical process leads to the formation of a radical anion which undergoes protonation by another benzamide molecule in DMF and DMSO or by the solvent in CH3CN and C2H5OH. Theoretical calculations have been performed to clarify the mechanism. Halobenzamide reduction involves the C-halogen bond breaking as the first reduction step to give benzamide.
ELECTROCHEMICAL REDUCTION OF BENZAMIDE AND THEIR O-HALO-DERIVATIVES AND P-HALO-DERIVATIVES IN NONAQUEOUS SOLVENTS / Benedetti, Luca; Borsari, Marco; Dallari, D; Fontanesi, Claudio; Grandi, G; Gavioli, Giovanna. - In: ELECTROCHIMICA ACTA. - ISSN 0013-4686. - STAMPA. - 39:(1994), pp. 2723-2728.