Skip to main content
Log in

Dissociation energies of O-H bonds in natural antioxidants

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

The dissociation energies of O-H bonds in natural antioxidants were estimated from the kinetic data (rate constants of reactions of the antioxidants with the peroxy radicals). The calculations were performed using the method of intersecting parabolas. α-Tocopherol was used as a reference phenol with D O-H = 330 kJ mol−1. The following groups of antioxidants were chosen for the estimation: tocopherols, their sulfur- and selenium-containing analogs, flavones, flavanones, and gallates. The discrepancy in the D O-H values for the same phenol by measurements of k(RO2 · + ArOH) of different authors does not exceed 2 kJ mol−1. The D O-H values were calculated for 64 phenols.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. E. T. Denisov, I. B. Afanas’ev, Oxidation and Antioxidants in Organic Chemistry and Biology, CRC Press, Taylor and Francis Group, Boca Raton, FL, 2005.

    Google Scholar 

  2. Oxidative Stress, Oxidants and Antioxidants, Ed. H. Sies, Academic Press, New York, 1991.

    Google Scholar 

  3. E. B. Burlakova, S. A. Krashakov, N. G. Khrapova, Khim. Fiz., 1995, 14, No. 10, 151 [Chem. Phys. Reports, 1995, 14, 1657 (Engl. Transl.)].

    CAS  Google Scholar 

  4. G. A. Burton, K. U. Ingold, Acc. Chem. Res., 1986, 19, 194.

    Article  CAS  Google Scholar 

  5. D. Rajalakshmi, R. Narasimhau, in Food Antioxidants, Eds D. L. Madhavi, S. S. Deshpande, D. K. Salunkhe, Dekker, New York, 1996, 65.

    Google Scholar 

  6. S. V. Jovanovic, S. Steenken, M. G. Simic, Y. Hara, in Flavonoids in Health and Disease, Eds C. A. Rice-Evans, L. Packer, Dekker, New York, 1998, 137.

    Google Scholar 

  7. Y.-R. Luo, Handbook of Bond Dissociation Energies in Organic Compounds, CRC Press, Boca Raton, FL, 2003.

    Google Scholar 

  8. E. T. Denisov, T. G. Denisova, Handbook of Antioxidants. Bond Dissociation Energies, Rate Constants, Activation Energies and Enthalpies of Reactions, CRC Press, Boca Raton, FL, 2000.

    Google Scholar 

  9. E. T. Denisov, Zh. Fiz. Khim., 1995, 69, 623 [Russ. J. Phys. Chem., 1995, 69, 563 (Engl. Transl.)].

    CAS  Google Scholar 

  10. T. G. Denisova, E. T. Denisov, Polym. Deg. Stab., 1998, 60, 345.

    Article  CAS  Google Scholar 

  11. E. T. Denisov, V. E. Tumanov, Usp. Khim., 2005, 74, 905 [Russ. Chem. Rev., 2005, 74, 825 (Engl. Transl.)].

    Google Scholar 

  12. E. T. Denisov, Usp. Khim., 1997, 66, 953 [Russ. Chem. Rev., 1997, 66, 859 (Engl. Transl.)].

    CAS  Google Scholar 

  13. E. T. Denisov, Models for Abstraction and Addition Reactions of Free Radicals, in General Aspects of the Chemistry of Radicals, Ed. Z. B. Alfassi, Wiley, Chichester, 1999, p. 79.

    Google Scholar 

  14. E. T. Denisov, Zh. Fiz. Khim., 1993, 67, 2416 [Russ. J. Phys. Chem., 1993, 67, No. 12 (Engl. Transl.)].

    CAS  Google Scholar 

  15. T. G. Denisova, E. T. Denisov, Neftekhimiya, 2004, 44, 278 [Petroleum Chem., 2004, 44, 250 (Engl. Transl.)].

    CAS  Google Scholar 

  16. L. R. C. Barclay, M. R. Vinqvist, K. Mukai, S. Itoh, H. Morimoto, J. Org. Chem., 1993, 58, 7416.

    Article  CAS  Google Scholar 

  17. H. A. Zahalka, B. Robillard, L. Hughes, J. Lusztyk, G. W. Burton, E. G. Janzen, Y. Kotake, K. U. Ingold, J. Org. Chem., 1988, 53, 3739.

    Article  CAS  Google Scholar 

  18. S. Kumar, H. Johansson, L. Engman, L. Valgimigli, R. Amorati, M. G. Fumo, G. F. Pedulli, J. Org. Chem., 2007, 72, 2583.

    Article  CAS  Google Scholar 

  19. V. V. Naumov, N. G. Khrapova, Biofizika, 1985, 30, 5 [Russ. Biophys., 1985, 33, No. 1 (Engl. Transl.)].

    CAS  Google Scholar 

  20. P. Pedrielli, G. F. Pedulli, L. H. Skibsted, J. Agric. Food. Chem., 2001, 49, 3034.

    Article  CAS  Google Scholar 

  21. M. Foti, M. Piattelli, M. T. Baratta, G. Ruberto, J. Agric. Food. Chem., 1996, 44, 497.

    Article  CAS  Google Scholar 

  22. V. Roginsky, Arch. Biochem. Biophys., 2003, 414, 261.

    Article  CAS  Google Scholar 

  23. M. Foti, G. Ruberto, J. Agric. Food. Chem., 2001, 49, 342.

    Article  CAS  Google Scholar 

  24. S. V. Jovanovic, S. Steenken, M. Tosic, B. Marjanovic, M. G. Simic, J. Am. Chem. Soc., 1994, 116, 4846.

    Article  CAS  Google Scholar 

  25. V. A. Belyakov, V. A. Roginsky, W. Bors, J. Chem. Soc., Perkin Trans. 2, 1995, 2319.

  26. V. A. Kostyuk, A. I. Potapovich, Arch. Biochem. Biophys., 1998, 355, 43.

    Article  CAS  Google Scholar 

  27. W. Bors, C. Michel, Free Radic. Biol. Med., 1999, 27, 1413.

    Article  CAS  Google Scholar 

  28. N. N. Pozdeeva, I. K. Yakushchenko, A. L. Aleksandrov, V. B. Luzhkov, E. T. Denisov, Kinet. Katal., 1989, 30, 31 [Kinet. Catal., 1989, 30 (Engl. Transl.)].

    CAS  Google Scholar 

  29. M. I. de Heer, P. Mulder, H.-G. Korth, K. U. Ingold, J. Lusztyk, J. Am. Chem. Soc., 2000, 122, 2355.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to E. T. Denisov.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1824–1832, September, 2008.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Denisova, T.G., Denisov, E.T. Dissociation energies of O-H bonds in natural antioxidants. Russ Chem Bull 57, 1858–1866 (2008). https://doi.org/10.1007/s11172-008-0251-0

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-008-0251-0

Key words

Navigation