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Voltammetric study of the oxidation of quercetin and catechin in the presence of cyanide ion

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Abstract

The reaction of electrochemically generated o-benzoquinones from oxidation of quercetin and catechin as Michael acceptors with cyanide ion as nucleophile has been studied using cyclic voltammetry. The reaction mechanism is believed to be EC; including oxidation of catechol moiety of these antioxidants followed by Michael addition of cyanide ion. The observed homogeneous rate constants (k obs) for reactions were estimated by comparing the experimental voltammetric responses with the digitally simulated results based on the proposed mechanism. The effects of pH and nucleophile concentration on voltammetric behavior and the rate constants of chemical reactions were also described.

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References

  1. B. Halliwell, J.M. Gutteridge, Free Rad. Biol. Med. 18, 125 (1995)

    Article  CAS  Google Scholar 

  2. P. Janeiro, A.M. Oliveira Brett, Anal. Chim. Acta 518, 109 (2004)

    Article  CAS  Google Scholar 

  3. M. Rafiee, Synlett 3, 503 (2007)

    Article  Google Scholar 

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

    Book  Google Scholar 

  5. J.B. Harborne, C.A. Williams, Phytochemistry 55, 481 (2000)

    Article  CAS  Google Scholar 

  6. G.S. Borghetti, I.S. Lula, R.D. Sinisterra, V.L. Bassani, AAPS Pharm. Sci. Tech. 10, 235 (2009)

    Article  CAS  Google Scholar 

  7. M. Duenas, S. Gonzalez-Manzano, A. Gonzalez-Paramas, C. Santos-Buelga, J. Pharm. Biomed. Anal. 51, 443 (2010)

    Article  CAS  Google Scholar 

  8. S.W. Huang, E.N. Frankel, J. Agric. Food Chem. 45, 3033 (1997)

    Article  CAS  Google Scholar 

  9. O. Korbut, M. Buckova, J. Labuda, P. Grundler, Sensors 3, 1 (2003)

    Article  CAS  Google Scholar 

  10. D. Abd El-Hady, Anal. Chim. Acta 593, 178 (2007)

    Article  CAS  Google Scholar 

  11. B. Yang, A. Kotani, K. Arai, F. Kusu, Anal. Sci. 17, 599 (2001)

    Article  CAS  Google Scholar 

  12. D. Nematollahi, M. Malakzadeh, J. Electroanal. Chem. 547, 191 (2003)

    Article  CAS  Google Scholar 

  13. H.P. Hendrickson, A.D. Kaufman, C.E. Lunte, J. Pharmaceut. Biomed. Anal. 12, 325 (1994)

    Article  CAS  Google Scholar 

  14. J. Ma, P.K. Dasgupta, Anal. Chim. Acta 673, 117 (2010)

    Article  CAS  Google Scholar 

  15. R.S. Nicholson, Anal. Chem. 37, 1351 (1965)

    Article  CAS  Google Scholar 

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

    Google Scholar 

  17. D. Nematollahi, M. Rafiee, L. Fotouhi, J. Iran. Chem. Soc. 6, 448 (2009)

    CAS  Google Scholar 

  18. D. Nematollahi, M. Alimoradi, S. Waqif Husain, Electroanalysis 16, 1359 (2004)

    Article  CAS  Google Scholar 

  19. D. Britz, Digital simulation in electrochemistry (Springer, Berlin Heidelberg, 2005)

    Google Scholar 

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

    Article  CAS  Google Scholar 

  21. A.J. Bard, L.R. Faulkner, Electrochemical methods, 2nd edn. (Wiley, New York, 2001), p. 237

    Google Scholar 

  22. L. Khalafi, M. Rafiee, J. Haz. Mat. 174, 801 (2010)

    Article  CAS  Google Scholar 

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Correspondence to Lida Khalafi.

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Khalafi, L., Rafiee, M. & Yadaei, F. Voltammetric study of the oxidation of quercetin and catechin in the presence of cyanide ion. Res Chem Intermed 37, 1047–1055 (2011). https://doi.org/10.1007/s11164-011-0312-0

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