Skip to main content
Log in

Kinetic isotope H/D effect in the oxidation of ethers of linoleic acid in solutions

  • Kinetics and Mechanism of Chemical Reactions. Catalysis
  • Published:
Russian Journal of Physical Chemistry B Aims and scope Submit manuscript

Abstract

It is shown that the initiated oxidation of deuterated esters of linoleic acid proceeds as a radical chain process. The value of the kinetic isotope effect for hydrogen atom abstraction from the bisallyl group of linoleic acid esters is determined: 3.0 for tert-butyl peroxy and cumylperoxy radicals.

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. J. A. Berliner, N. Leitinger, and S. Tsimikas, J. Lipid Res. 50 (Suppl.), 207 (2008).

    Article  Google Scholar 

  2. M. S. Shchepinov, Rejuvenation Res. 10, 47 (2007).

    Article  CAS  Google Scholar 

  3. M. S. Shchepinov, V. Choub, E. Pollock, et al., Toxicol. Lett. 207, 97 (2011).

    Article  CAS  Google Scholar 

  4. T. T. Reed, Free Radic. Biol. Med. 51, 1302 (2011).

    Article  CAS  Google Scholar 

  5. P. R. Angelova, M. H. Horrocks, D. Klenerman, et al., J. Neurochem. 133, 582 (2015).

    Article  CAS  Google Scholar 

  6. H. Zhong and H. Yin, Redox Biol. 4, 193 (2015).

    Article  CAS  Google Scholar 

  7. D. A. Butterfield and C. M. Lauderback, Free Radicals Biol. Med. 32, 1050 (2002).

    Article  CAS  Google Scholar 

  8. Z. S. Andrianova, N. N. Breslavskaya, E. M. Pliss, and A. L. Buchachenko, Russ. J. Phys. Chem. A 90, 1936 (2016).

    Article  CAS  Google Scholar 

  9. A. L. Buchachenko and E. M. Pliss, Russ. Chem. Rev. 85, 557 (2016).

    Article  CAS  Google Scholar 

  10. M. H. Glickman, J. S. Wiseman, and J. P. Klinman, J. Am. Chem. Soc. 116, 793 (1994).

    Article  CAS  Google Scholar 

  11. M. J. Knapp, K. Rickert, and J. P. Klinman, J. Am. Chem. Soc. 124, 3865 (2002).

    Article  CAS  Google Scholar 

  12. C. C. Hwang and C. B. Grissom, J. Am. Chem. Soc. 116, 795 (1994).

    Article  CAS  Google Scholar 

  13. C. R. Lamberson, L. Xu, H. Muchalski, et al., J. Am. Chem. Soc. 136, 838 (2014).

    Article  CAS  Google Scholar 

  14. S. Hill, C. R. Lamberson, L. Xu, et al., Free Radicals Biol. Med. 53, 893 (2012).

    Article  CAS  Google Scholar 

  15. A. Y. Andreyev, H. S. Tsui, G. L. Milne, et al., Free Radicals Biol. Med. 82, 63 (2015).

    Article  CAS  Google Scholar 

  16. M. S. Shchepinov, V. A. Roginsky, J. T. Brenna, et al., Omega-3 Fatty Acids in Brain and Neurological Health (Elsevier, Amsterdam, 2014), p.373.

    Google Scholar 

  17. K. W. Rickert and J. P. Klinman, Biochemistry 38, 12218 (1999).

    Article  CAS  Google Scholar 

  18. P. Phatak, J. Venderley, J. Debrota, J. Li, and S. S. Iyengar, J. Phys. Chem. B 119, 9532 (2015).

    Article  CAS  Google Scholar 

  19. L. Bedard, M. J. Young, D. Hall, T. Paul, and K. U. Ingold, J. Am. Chem. Soc. 123, 12439 (2001).

    Article  CAS  Google Scholar 

  20. J. P. Klinman, Chem. Phys. Lett. 471 (4–6), 179 (2009).

    Article  CAS  Google Scholar 

  21. V. A. Roginskii, Russ. J. Phys. Chem. B 9, 352 (2015).

    Article  CAS  Google Scholar 

  22. S. Hill, K. Hirano, V. V. Shmanai, et al., Free Radicals Biol. Med. 50, 130 (2011).

    Article  CAS  Google Scholar 

  23. D. Loshadkin, V. Roginsky, and E. Pliss, Int. J. Chem. Kinet. 34, 162 (2002).

    Article  CAS  Google Scholar 

  24. J. A. Howard and K. U. Ingold, Can. J. Chem. 45, 793 (1967).

    Article  CAS  Google Scholar 

  25. N. A. Porter, Acc. Chem. Res. 19, 262 (1986).

    Article  CAS  Google Scholar 

  26. B. Roschek, K. A. Tallman, C. L. Rector, et al., J. Org. Chem. 71, 3527 (2006).

    Article  CAS  Google Scholar 

  27. D. A. Pratt, K. A. Tallman, and N. A. Porter, Acc. Chem. Res. 44, 458 (2011).

    Article  CAS  Google Scholar 

  28. H. Yin, L. Xu, and N. A. Porter, Chem. Rev. 111, 5944 (2011).

    Article  CAS  Google Scholar 

  29. C. L. Perrin and K. D. Burke, J. Phys. Chem. A 119, 5009 (2015).

    Article  CAS  Google Scholar 

  30. H. Kitaguchi, K. Ohkubo, S. Ogo, and S. Fukuzumi, Chem. Commun., No. 9, 979 (2006).

    Article  Google Scholar 

  31. NIST Chemical Kinetics Database. http://kinetics. nist.gov/kinetics/index.jsp.

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to E. M. Pliss.

Additional information

Original Russian Text © I.V. Tikhonov, I.V. Moskalenko, E.M. Pliss, M.A. Fomich, A.V. Bekish, V.V. Shmanai, 2017, published in Khimicheskaya Fizika, 2017, Vol. 36, No. 5, pp. 14–18.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Tikhonov, I.V., Moskalenko, I.V., Pliss, E.M. et al. Kinetic isotope H/D effect in the oxidation of ethers of linoleic acid in solutions. Russ. J. Phys. Chem. B 11, 395–399 (2017). https://doi.org/10.1134/S1990793117030113

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1990793117030113

Keywords

Navigation