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Voltammetric analysis of the possibility of derivatization of levodopa in the presence of aniline derivatives

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Abstract

Electrochemical oxidation of levodopa (LD) as one of the most well-known neurotransmitters has been studied in the presence of some aniline derivatives. The electron transfer of LD is followed by two competitive reactions in the presence of these amines. The reactions are the Michael additions of side chain amine group of LD and/or aromatic amines to electrochemically generated o-quinone. There are two ECE mechanisms for both pathways and the competition between these inter and intramolecular reactions drastically depends on the pH of the medium. The pH dependence of reactions has been studied and the observed homogeneous rate constants of the reactions were estimated by digital simulation of cyclic voltammograms. The effect of aniline substituents was also studied with regard to their reactivities toward o-quinone of LD and the competitive reactions. Based on the obtained results, the products of intermolecular reactions are electroactive diphenylamine derivatives and their half-wave potentials depend on the nature of the aniline substituent.

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Authors and Affiliations

  1. Department of Chemistry, Shahr-e-Qods Branch, Islamic Azad University, Tehran, Iran

    Lida Khalafi & Mojgan Khoshnam

  2. Department of Chemistry, Institute for Advanced Studies in Basic Sciences, Zanjan, Iran

    Mohammad Rafiee

  3. Department of Chemistry, Zanjan Branch, Islamic Azad University, Zanjan, Iran

    Seyed Mohammad Shoaei

Authors
  1. Lida Khalafi
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  2. Mohammad Rafiee
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  3. Mojgan Khoshnam
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  4. Seyed Mohammad Shoaei
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Correspondence to Lida Khalafi.

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Khalafi, L., Rafiee, M., Khoshnam, M. et al. Voltammetric analysis of the possibility of derivatization of levodopa in the presence of aniline derivatives. J IRAN CHEM SOC 10, 1257–1262 (2013). https://doi.org/10.1007/s13738-013-0263-z

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  • DOI: https://doi.org/10.1007/s13738-013-0263-z

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