Electrochemical behavior of 2-aminodiphenylamine and efficient factors on the site-selectivity of sulfonylation reaction: Experimental and theoretical studies

- Electrochemical dimerization of 2-aminodiphenylamine.
- The effect of natural charge on site selectivity.
- The effect of thermodynamic stability of products on site selectivity.
- Antimicrobial activity of synthesized compounds.
- Galvanostatic conditions for electrosynthesis.

The electrochemical dimerization of 2-aminodiphenylamine (2ADPA) has been studied. The data indicate that electrochemically generated (Z)-N-(6-iminocyclohexa-2,4-dien-1-ylidene) aniline (2ADPAox) can serve as a Michael acceptor in the reaction with starting molecular (2ADPA) form and converts to the corresponding dimer. The mechanism of dimerization has been studied using both controlled-potential coulometry and cyclic voltammetry. The anodic dimerization of 2-aminodiphenylamine has been successfully performed under constant current condition in good yield and purity in an undivided cell. Furthermore, electrochemical oxidation of 2ADPA has been studied both experimentally and theoretically to provide insight into the influence of some factors on the type of chemical reaction which follows 2ADPAox. The effect of natural charge of 2ADPAox on the reaction site was calculated using PBE/def2-SVP level of theory to identify regioselective sulfonation of 2ADPA. The results indicate that the natural charge of Michael acceptor 2ADPAox and thermodynamic stability of products lead to site-selectivity sulfonylation of 2ADPA. In addition, the sulfone products were evaluated for their in vitro antibacterial activity against two bacterial ATCC strains (Staphylococcus aureus, and Escherichia coli).

The anodic dimerization of 2-aminodiphenylamine has been successfully performed under constant current condition in good yield and purity in an undivided cell.