Electrochemical Studies of Nitroheterocyclic Compounds of Biological Interest. VII. Effect of Electrode Material

Abstract

The electrochemical behaviour of three nitrofuran compounds, nitrofurazone, nitrofurantoin and furazolidone, has been studied in three solvent types; aprotic, aqueous and mixed, and at four working electrodes. Particular attention has focused on the 1-electron RNO2/RNO2.- couple as measured by the cyclic voltammetric mode. Using Hg in aqueous buffer, reduction of the NO2 group proceeds directly to the hydroxylamine with no intermediate stages being identified. Addition of an aprotic solvent gave a 2-stage reduction, initially forming the RNO2.- species. At all solid electrodes, however, the RNO2/RNO2.- couple was identified under simple aqueous conditions. The switch to a mixed aqueous/aprotic solvent medium produced only minor changes in the response compared with the situation on Hg. This presents the opportunity of using nitrofuran complexes as model systems for the redox behaviour of nitro aromatic compounds in general at solid electrode surfaces where the latters' more negative reduction potentials makes direct study difficult. The conditions have been defined whereby we can examine pH effects and RNO2.- biological target interactions in simple aqueous media to allow the further refinement of the electrolytic model system for studying bio-reducible drug action.