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Electrochemical oxidation of 2,5-diethoxy 4-morpholinoaniline in the presence of thiobarbituric acid: present an ECCCEC Mechanism

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Abstract

The electrochemical oxidation of 2,5-diethoxy-4-morpholinoaniline has been studied in the presence of thiobarbituric acid by the use of experimental and calculation methods. Cyclic voltammetry, controlled-potential coulometry and density functional theory (DFT) were used in this study. By the use of the cyclic voltammetry, the best condition of synthesis was obtained, and controlled-potential coulometry was performed under this condition. The results indicated that the produced p-benzoquinonediimine is unstable, and it was hydrolyzed in the experimental condition. It was found that the produced p-quinoneimine from oxidation/hydrolysis of 2,5-diethoxy-4-morpholinoaniline reacts with the thiobarbituric acid as a nucleophile and via an ECCCEC mechanism converts to the product. Also, computational calculations were used to analyze oxidation peaks in voltammetry. DFT, BP86 level of theory and 6-31G(p,d) basis set, was used to obtain the theoretical results.

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Authors and Affiliations

  1. Faculty of Science, Malayer University, 65719, Malayer, Iran

    Hadi Beiginejad

  2. Faculty of Chemistry, Bu-Ali-Sina University, P. O. Box 65174, Hamedan, Iran

    Davood Nematollahi

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  1. Hadi Beiginejad
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  2. Davood Nematollahi
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Correspondence to Hadi Beiginejad.

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Beiginejad, H., Nematollahi, D. Electrochemical oxidation of 2,5-diethoxy 4-morpholinoaniline in the presence of thiobarbituric acid: present an ECCCEC Mechanism. J IRAN CHEM SOC 16, 2177–2185 (2019). https://doi.org/10.1007/s13738-019-01687-2

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  • DOI: https://doi.org/10.1007/s13738-019-01687-2

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