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Electrochemical oxidation of catecholamines in the presence of aromatic amines: interplay between inter- and intramolecular nucleophilic addition

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Abstract

The reactions of electrochemically generated o-quinones from oxidation of catecholamines with aniline derivatives have been studied using cyclic voltammetry. There is a close and pH-dependent interplay between intra and intermolecular Michael addition reactions of side chain amine group of catecholamines and anilines toward the electrochemically generated o-quinone. The pH dependence of reactions has been studied and the condition for domination of each reaction was obtained. The observed homogeneous rate constants of reactions were estimated by digital simulation of cyclic voltammograms for each pathway. The reactivities and the rate constants of Michael addition of anilines depend on the electron-withdrawing character of their substituent, which have been studied quantitatively.

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References

  1. M.R. Pranzatelli, Exp. Neurol. 125, 142 (1994)

    Article  CAS  Google Scholar 

  2. M.D. Hawley, S.V. Tatawawadi, S. Piekarskiani, R.N. Adams, J. Am. Chem. Soc. 89, 447 (1967)

    Article  CAS  Google Scholar 

  3. J. Li, B.M. Christensen, J. Electroanal. Chem. 375, 219 (1994)

    Article  CAS  Google Scholar 

  4. A. Afkhami, D. Nematollahi, L. Khalafi, M. Rafiee, Int. J. Chem. Kinet. 37, 17 (2005)

    Article  CAS  Google Scholar 

  5. A. Brun, R. Rosset, J. Electroanal. Chem. 49, 287 (1974)

    Article  CAS  Google Scholar 

  6. Y. Song, J.F. Zhou, Y. Song, Y. Wei, H. Wang, Bioorg. Med. Chem. Lett. 15, 4671 (2005)

    Article  CAS  Google Scholar 

  7. E. Winter, L. Codognoto, S. Rath, Electrochim. Acta 51, 1282 (2006)

    Article  CAS  Google Scholar 

  8. S. Fahn, Mov. Disord. 23, 497 (2008)

    Article  Google Scholar 

  9. I. Abboud, N. Lerolle, S. Urien, J.M. Tadie, F. Leviel, J.Y. Fagon, C. Faisy, Crit. Care 13, 120 (2009)

    Article  Google Scholar 

  10. S. Sircar, Principal of medical physiology (Thieme, Germany, 2007)

    Google Scholar 

  11. E. Nalewajko, A. Wiszowata, A. Kojlo, J. Pharm. Biomed. 43, 1673 (2007)

    Article  CAS  Google Scholar 

  12. B.M. Berecek, M.J. Brody, Am. J. Physiol. 242, 593 (1982)

    Google Scholar 

  13. E. Grana, P. Pratesi, L. Villa, Br. J. Pharmacol. 34, 694 (1968)

    Google Scholar 

  14. F. Siopa, A.S. Pereira, L.M. Ferreira, M.M. Marques, P.S. Branco, Bioorg. Chem. 44, 19 (2012)

    Article  CAS  Google Scholar 

  15. R. Xu, X. Huang, K.J. Kramer, M.D. Hawley, Bioorg. Chem. 24, 110 (1996)

    Article  CAS  Google Scholar 

  16. B.J. Venton, R.M. Wightman, Anal. Chem. 75, 414A (2003)

    Article  CAS  Google Scholar 

  17. D.C.S. Tse, R.L. McCreery, R.N. Adams, J. Med. Chem. 19, 37 (1976)

    Article  CAS  Google Scholar 

  18. N. Zhang, X.F. Guo, H. Wang, H.S. Zhang, Anal. Bioanal. Chem. 401, 297 (2011)

    Article  CAS  Google Scholar 

  19. D.K. Gosser, Cyclic voltammetry: simulation and analysis of reaction mechanisms (Wiley VCH, New York, 1993)

    Google Scholar 

  20. M. Rafiee, L. Khalafi, Electrochim. Acta 55, 1809 (2010)

    Article  CAS  Google Scholar 

  21. N.D. Danielson, P.A. Gallagher, J.J. Bao, Chemical Reagents and Derivatization Procedures, in Drug Analysis in Encyclopedia of Analytical Chemistry, ed. by R.A. Meyers (Wiley, Chichester, 2000), pp. 7042–7076

    Google Scholar 

  22. J.M. Saveant, Elements of molecular and biomolecular electrochemistry (Willey-VCH, New Jersey, 2006)

    Book  Google Scholar 

  23. D. Cairns, Essentials of Pharmaceutical Chemistry, 3rd edn. (Pharmaceutical Press, UK, 2008)

    Google Scholar 

  24. L. Khalafi, M. Rafiee, F. Yadaei, Res. Chem. Intermed. 37, 1047 (2011)

    Article  CAS  Google Scholar 

  25. W.H. Brown, C.S. Foote, B.L. Iverson, E. Anslyn, Organic Chemistry, 5th edn. (Brooks Cole, USA, 2009)

    Google Scholar 

  26. A. Afkhami, D. Nematollahi, T. Madrakian, L. Khalafi, Electrochim. Acta 50, 5633 (2005)

    Article  CAS  Google Scholar 

  27. A.R. Campanelli, A. Domenicano, F. Ramondo, J. Phys. Chem. A 107, 6429 (2003)

    Article  CAS  Google Scholar 

  28. D. Nematollahi, A. Afkhami, F. Mosaed, M. Rafiee, Res. Chem. Intermed. 30, 299 (2004)

    Article  CAS  Google Scholar 

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Authors and Affiliations

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

    Lida Khalafi & Maryam Norouznia

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

    Mohammad Rafiee & Yosef Abdossalami Asl

Authors
  1. Lida Khalafi
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  2. Mohammad Rafiee
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  3. Maryam Norouznia
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  4. Yosef Abdossalami Asl
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Correspondence to Lida Khalafi.

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Khalafi, L., Rafiee, M., Norouznia, M. et al. Electrochemical oxidation of catecholamines in the presence of aromatic amines: interplay between inter- and intramolecular nucleophilic addition. Res Chem Intermed 41, 7151–7162 (2015). https://doi.org/10.1007/s11164-014-1803-6

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  • DOI: https://doi.org/10.1007/s11164-014-1803-6

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