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Abstract
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Electrochemical redox reactions produce high reactive intermediates, such as: anions, cations, radical ions, radicals and nucleophilic as well as electrophilic groups. In this work, the pH dependent anodic behavior of 3,3'-Dimethylbenzidine (OTD) was investigated. Our data shows that the EpA–pH diagram indicates the presence of three predominant regions. The predominant species across all regions were identified. Furthermore, the electrochemical oxidation of orthotolidine in the presence of 4-methylbenzenesulfinate as a nucleophile has been investigated. The controllable electron transfer process causes to change the electronpoor and electrophilic character of a functional group to be nucleophilic or vice versa. The synthesis of this compound was performed by anodic oxidation of 3,3'-Dimethylbenzidine (OTD) in the presence of benzenesulfinic acid (BSA) in aqueous acetate buffer solution, using a carbon electrode. The cyclic voltammogram of OTD shows an reversible anodic peak corresponding to two-electron oxidation of OTD, while, the CV of the mixture of OTD and BSA two anodic irreversible peak which is a confirmation of the reaction between electrogenerated OTDox and BSA. Based on the electrochemical evidence, The synthesis of the desired derivative was conducted in aqueous buffer (pH =1.0, HClO4 c = 0.1 M), by controlled potential method (at 0.57 V vs. Ag/AgCl electrode), under green conditions. Product formation was confirmed by using IR, MS and NMR spectra.
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