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Thermodynamic dependence of the electrochemical oxidation of dihydroxybenzenes in the presence of some Meldrum's acids

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Abstract

Electrochemical oxidation of some dihydroxybenzene derivatives in the presence of methyl-Meldrum's acid (MMA) and phenyl-Meldrum's acid (PMA) as nucleophiles were investigated both experimentally and theoretically. Using recorded E-pH diagrams of some catechol derivatives, Ep0 of the studied species were obtained. Also, ∆Gtot of the electrochemical oxidation of the catechols have been calculated using different computational methods. Then, by the use of Ep0 vs. ∆Gtot graphs, it was found that BP86/6-31G(d,p) is the best method and it was selected for other computational studies. Electrolysis of the catechols in the presence of MMA and PMA was performed, and the results indicate that the final products are produced via an EC mechanism. The electrochemical oxidation of hydroquinone species in the presence of the nucleophiles was studied too. It was found that unlike what was observed for catechols, the electrochemical oxidation of hydroquinones in the presence of MMA and PMA is ECE. Also, the mechanism of the electrochemical oxidation of hydroquinone in the presence of MMA changed to ECECE due to the changing condition of the electrolysis. Different electrochemical behaviors of the studied dihydroxybenzenes in the presence of the nucleophiles were analyzed by the computational study, and the results indicate that although the mechanisms are not the same, all of them proceed in the thermodynamically favored directions.

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Acknowledgments

We acknowledge the Malayer University Research Council and our Partners of Analytical Chemistry Laboratory in Malayer University for their support of this work.

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Authors and Affiliations

  1. Faculty of Science, Malayer University, 65174, Malayer, Iran

    Shiva Aslemarz, Hadi Beiginejad & Narges Pakravan

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  1. Shiva Aslemarz
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  2. Hadi Beiginejad
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  3. Narges Pakravan
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Correspondence to Hadi Beiginejad.

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Aslemarz, S., Beiginejad, H. & Pakravan, N. Thermodynamic dependence of the electrochemical oxidation of dihydroxybenzenes in the presence of some Meldrum's acids. Monatsh Chem 150, 1433–1444 (2019). https://doi.org/10.1007/s00706-019-02443-1

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  • DOI: https://doi.org/10.1007/s00706-019-02443-1

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