Electrochemical study of 2-amino-5-mercapto-1,3,4-thiadiazole in the absence and presence of p-benzoquinone: an efficient strategy for the electrosynthesis of new 1,3,4-thiadiazole derivatives

Abstract

In this study, first, the electrochemical behavior of 2-amino-5-mercapto-1,3,4-thiadiazole (AMT) was fully investigated in the absence and presence of electrochemically generated p-benzoquinone (p-BQ, which is the oxidized form of hydroquinone), as an electrophile, via cyclic voltammetry (CV) at a glassy carbon electrode (GCE) and in an acetic acid buffer (0.2 M)/ethanol solution mixture. Then, an E-pH diagram was proposed for different structures of AMT at various pH values. The obtained voltammograms also exhibited an "electron transfer + chemical reaction" (EC) mechanism. Besides the voltammetric exploration, electrosynthesis of new 1,3,4-thiadiazole derivatives was conducted by constant current electrolysis (CCE) as a facile and cost-effective method for the formation of S-S and S-C bonds. Finally, the biological activity of products was also analyzed via an in silico method.