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Anion radical formation in the reaction of chloranilic acid with n-methylpiperidine in acetonitrile

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Abstract

Reaction of chloranilic acid with N-methylpiperidine in acetonitrile has been studied. The product of the reaction is an unusually stable anion radical of quinone. The presence of radicals has been confirmed by EPR measurements. Stability constant, extinction coefficients and thermodynamic reaction parameters are reported. Mechanism of the reaction is proposed.

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REFERENCES

  1. Coenzyme Q Biochemistry, Bioenergetics and Clinical Applications of Ubiquinone; (G. Lenaz, Ed.). Wiley-Interscience, Chichester 1985.

    Google Scholar 

  2. K.T. Finley: Quinones as Synthones,in: The Chemistry of Quinonoid Compounds,Vol. II, Wiley, 1988.

  3. B.L. Trumpover, R.B. Gennis: Annu. Rev. Biochem.,63, 675 (1994).

    Google Scholar 

  4. Z. Rappoport: Acc. Chem. Res., 14, 7 (1981).

    Article  CAS  Google Scholar 

  5. Z. Rappoport: Acc. Chem. Res., 25, 474 (1992).

    Article  CAS  Google Scholar 

  6. J.K. Kochi: Acta Chem. Scand.,44, 409 (1990).

    Article  CAS  Google Scholar 

  7. N.L. Baud: Radicals, Ion Radicals, and Triplets, Wiley-VCH, 1997.

  8. M.M. Habeeb, H.A. Alwakil, A. El-Dissouky. H.A. Fattab: Pol. J. Chem., 69, 1428 (1995).

    CAS  Google Scholar 

  9. Y.M. Issa, A.E. El-Kholy, A.L. El-Ansary: Acta Chim. Hung., 118, 43 (1985).

    CAS  Google Scholar 

  10. E.H. El-Mossalamy, K.Y. El-Baradie: Monatsh. Chemie,128, 255 (1997).

    Article  CAS  Google Scholar 

  11. M.U. Adikwu, K.C. Ofokansi, A.A. Attama: Biol. Pharm. Bull., 21, 1243 (1998).

    CAS  Google Scholar 

  12. M.U. Adikwu, K.C. Ofokansi, A.A. Attama: Chem. Pharm. Bull., 47, 463 (1999).

    CAS  Google Scholar 

  13. H. Ishida, S. Kashino: Acta Cryst.,C55, 1923 (1999).

    CAS  Google Scholar 

  14. H. Ishida, S. Kashino: Acta Cryst.,C55, 1149 (1999).

    CAS  Google Scholar 

  15. T. Nogami, K. Yoshihara, H. Hosoya, S. Nagakura: J. Phys. Chem., 73, 2670 (1969).

    Article  CAS  Google Scholar 

  16. P.C. Dwiwedi, A.K. Banga, R. Agarval: Indian J. Chem., 24A, 459 (1985).

    Google Scholar 

  17. M.U. Adikwu, H-D. Holtje: Chem. Pharm. Bull., 49, 669 (2001).

    Article  CAS  Google Scholar 

  18. M. Dworniczak: React. Kinet. Catal. Lett., 46, 209 (1992).

    Article  CAS  Google Scholar 

  19. S.B. Shah, A.S.N. Murthy: J. Phys. Chem., 79, 322 (1975).

    Article  CAS  Google Scholar 

  20. Y.M. Issa: Spectrochim. Acta, 40A, 137 (1984).

    CAS  Google Scholar 

  21. G. Grampp S. Landgraf, K. Rasmussen: J. Chem. Soc., Perkin II, 1897 (1999).

  22. H.A. Torrey, W.H. Hunter: J. Am. Chem. Soc., 41, 702 (1912).

    Article  Google Scholar 

  23. P. Job: Ann Chim.,10, 113 (1928).

    Google Scholar 

  24. M.M. Ayad: Bull. Chem. Soc. Jpn.,70, 2369 (1997).

    Article  CAS  Google Scholar 

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  1. Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780, Poznan, Poland

    Miroslaw Dworniczak

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  1. Miroslaw Dworniczak
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Dworniczak, M. Anion radical formation in the reaction of chloranilic acid with n-methylpiperidine in acetonitrile. Reaction Kinetics and Catalysis Letters 78, 65–72 (2003). https://doi.org/10.1023/A:1022557731519

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