Electrochemical oxidation of 2,5-diethoxy-4-morpholinoaniline in the presence of ptoluenesulfinic acid: Experimental and theoretical study

Electrochemical oxidation of 2,5-diethoxy-4-orpholinoaniline (1) in aqueous solution has been investigatedboth experimentally and theoretically to bring hints into the connection of thermodynamic and oxidation potential. Theexperimental results were obtained using cyclic voltammetry and controlled potential coulometry. Also the theoreticalresults were calculated at DFT (B3LYP) level of theory and 6–311G (p,d) basis sets. The result of this work showsthat the electrochemical generated p-quinonedimine (1a) participates in the hydrolysis reaction and is converted to pbenzoquinone.It was found that species with larger ΔGtot value have more positive oxidation potentials. Alsoelectrochemical oxidation of 1 in the presence of p-toluenesulfinic acid (TSA) was studied in view point ofthermodynamic.

Keywords:

Cyclic voltammetry , para-quinonedimine , Hydrolysis , para-benzoquinone , Density Functional Theory