The Electrochemical Behaviour of Novel Multifunctional a-Hydroxymethylated Nitroalkenes at Glassy Carbon and Wax Impregnated Carbon Paste Electrodes

Abstract

The electrochemical behaviour of novel multifunctional α- hydroxymethylated nitroalkenes was studied with respect to oxidation of -OH moiety and reduction of nitro group using the cyclic voltammetric technique at glassy carbon and wax impregnated carbon paste electrodes with sulphuric acid as the supporting electrolyte. The -OH moiety attached to the nitroalkene side chain was found to undergo irreversible four electrons electrochemical oxidation to form an acid at the glassy carbon electrode but no oxidation was observed at the wax impregnated carbon paste electrode. Oxidation in sulphuric acid medium becomes easier with increasing the sulphuric acid concentration. This unusual behaviour is attributed to the formation of a six-membered cyclic structure at lower concentrations of sulphuric acid due to intramolecular hydrogen bonding. Going to the lower potential range, reduction of nitro group was observed in sulphuric acid medium both at the glassy carbon and wax impregnated carbon paste electrodes. A comparative study indicated easier reduction at the glassy carbon electrode. Non hydroxymethylated beta nitroalkenes undergo reduction at a lower negative potential compared to the corresponding α-hydroxymethylated nitroalkenes.