Abstract
The electrochemical oxidation of several Biginelli compounds in acetonitrile at different pH values was carried out. The influence of the substituents at the heterocyclic ring was studied in tetrabutylammonium perchlorate by linear and sweep voltamperometry with platinum rotatory disc. Cyclic voltamperometry, controlled potential electrolysis and EPR techniques were used in order to determine the oxidation mechanisms. In acidic medium all derivatives follow an oxidation mechanism with an ECE (Electrochemical, Chemical, Electrochemical process), sequence. On the other hand, in basic media the derivatives obey a DISP1 (Disproportionation) mechanism, whereas the uptake of the proton at N1 by the OH- ion of the medium was the rate determining step. The effect of different substituents in the compounds was studied by using the theoretical ionization potential and the half wave oxidation potential correlation, as. It was found that there is an acceptable relationship between these parameters. The electrosynthesis of the para-nitro derivative was carried out in order to characterize the corresponding oxidation product.
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