Voltammetric study of the reaction of the 2-cyanophenoxide anion with carbon dioxide in dimethylformamide

Abstract

The electrochemical reduction of 2-cyanophenol was studied in dimethylformamide (DMF) at a platinum microdisk electrode in the absence of carbon dioxide and with saturations of 10% and 100% carbon dioxide. Upon introduction of carbon dioxide it was inferred that the 2-cyanophenoxide anion, formed after the reduction of 2-cyanophenol and concomitant rapid protonation of the radical anion, reacts with carbon dioxide to form a possible cyanophenoxide–carbon dioxide complex. The latter then undergoes further protonation from the parent 2-cyanophenol. The complex formed undergoes further electrochemical reduction at the platinum electrode, introducing a new voltammetric reduction wave. UV/visible and IR spectroscopic studies confirm these inferences.