Electrochemical oxidation of p-phenylenediamine in the presence of p-toluenesulfinic acid, a green synthesis of a novel diphenylsulfone derivative. Investigating some effective factors on the rate of hydrolysis
摘要
In this study, the electrochemical oxidation of p-phenylenediamine in the presence of p-toluenesulfinic acid as a nucleophile was studied using cyclic voltammetry and controlled-potential coulometry. The results indicate that the electrogenerated p-benzoquinonediimine is unstable and hydrolyzed, but in the presence of p-toluenesulfinic acid, the p-benzoquinonediimine reacts with it and via an, EC mechanism, a new diphenylsulfone species is produced. This work provides a facile and environmentally friendly reagent-less electrochemical method for synthesis of a new diphenylsulfone derivative in aqueous solution with good yield. The effect of the protonation of p-benzoquinonediimines (1H2ox2+ and 3bH22+) on the hydrolysis reaction was investigated using computational analysis. It was shown the charge of the reaction site and N = C bond order (WBIs) are effective on the hydrolysis reaction.