Advertisement

Thiyl Free Radicals: Electron Transfer, Addition or Hydrogen Abstraction Reactions in Chemistry and Biology, and the Catalytic Role of Sulphur Compounds

  • Christina Dunster
  • Robin L. Willson
Part of the NATO ASI Series book series (NSSA, volume 197)

Abstract

Organic chemists have long been familiar with the variety of addition and hydrogen transfer reactions that thiyl free radicals (RS25CF) can undergo, and of the chain processes and relatively fast reversible reactions that can often take place.

Keywords

Hydrogen Transfer Electron Transfer Reaction Pulse Radiolysis Aqueous Methanol Solution Thiyl Radical 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    W. A. Waters, “The Chemistry of Free Radicals”, Oxford University Press, London(1946).Google Scholar
  2. 2.
    W. A. Pryor, “Mechanisms of Sulphur Reactions”, McGraw-Hill, New York, p. 75–93, (1962).Google Scholar
  3. 3.
    A. Ohno and S. Oae, in: “Organic Chemistry of Sulphur”, S. Oae, ed., Plenum Press, New York and London, p. 119–186, (1975).Google Scholar
  4. 4.
    M. S. Kharasch, A. T. Read, and F. R. Mayo, Chem. and Ind. (London), 57: 792 (1938).Google Scholar
  5. 5.
    A. F. Bickel and E. C. Kooijman, Nature, 170: 211 (1952).CrossRefGoogle Scholar
  6. 6.
    E. F. P. Harris and W. A. Waters, Nature, 170: 212 (1952).CrossRefGoogle Scholar
  7. 7.
    C. Walling and W. Helmreich, J. Amer. Chem. Soc., 81: 1144 (1959).CrossRefGoogle Scholar
  8. 8.
    A. L. J. Beckwith and L. B. See, Austr. J. Chem., 17: 109 (1964).CrossRefGoogle Scholar
  9. 9.
    M. S. Kharasch, W. Nudenberg, and G. J. Mantell, J. Org. Chem., 16: 524 (1951).CrossRefGoogle Scholar
  10. 10.
    H. Bredereck, A. Wagner, and A. Kottenhahn, Chem. Ber., 93: 2415 (1960).CrossRefGoogle Scholar
  11. 11.
    A. A. Oswald and T. J. Wallace, in: “Organic Sulfur Compounds”, “Anionic Oxidation of Thiols and Co-oxidation of Thiols with Olefins”, N. Kharasch and C. Y. Meyers, eds., Pergamon Press, New York, Vol. 2, pp. 205–232 (1966).Google Scholar
  12. 12.
    K. E. J. Barrett and W. A. Waters, Discussions Faraday Soc., 14: 221 (1953).CrossRefGoogle Scholar
  13. 13.
    G. E. Adams, G. S. McNaughton, and B. D. Michael, in: “In Excitation and Ionisation”, G. Scholes and G. R. A. Johnson, eds., Taylor and Francis, London, pp. 281–293, (1967).Google Scholar
  14. 14.
    G. E. Adams, G. S. McNaughton, and B. D. Michael, Trans. Faraday Soc., 64: 902 (1968).CrossRefGoogle Scholar
  15. 15.
    G. E. Adams, R. C. Armstrong, A. Charlesby, B. D. Michael, and R. L. Willson, Trans. Faraday Soc., 65: 732 (1969).CrossRefGoogle Scholar
  16. 16.
    J. L. Redpath, Radiat. Research, 54: 364 (1973).CrossRefGoogle Scholar
  17. 17.
    T. Miyashita, M. lion, and M. Matsuda, Bull. Chem. Soc. Jpn., 50: 317 (1977).CrossRefGoogle Scholar
  18. 18.
    W. A. Pryor, G. Gojon, and D. F. Church, J. Org. Chem., 43: 793 (1978).CrossRefGoogle Scholar
  19. 19.
    M. Morita, K. Sasai, M. Tajima, and M. Fujimaki, Bull. Chem. Soc. Jpn., 44: 2257 (1971).CrossRefGoogle Scholar
  20. 20.
    A. J. Elliot and F. C. Sopchyshyn, Radiat. Phys. Chem., 19: 417 (1982).Google Scholar
  21. 21.
    A. J. Elliot, A. S. Simsons, and F. C. Sopchyshyn, Radiai. Phys. Chem., 23: 377 (1984).Google Scholar
  22. 22.
    K. Schäfer and K-D. Asmus, J. Phys. Chem., 85: 852 (1981).CrossRefGoogle Scholar
  23. 23.
    M. S. Akhlaq, H-P. Schuchmann, and C. von Sonntag, Int. J. Radiat. Biol., 51: 91 (1987).CrossRefGoogle Scholar
  24. 24.
    C. Schöneich, M. Bonifacic, and K-D. Asmus, Free Radical Res. Commun., 6: 393 (1989).CrossRefGoogle Scholar
  25. 25.
    C. Schöneich, K-D. Asmus, U. Dillinger, and F. V. Bruchausen, Biochem. Biophys. Res. Commun., 161: 113 (1989).CrossRefGoogle Scholar
  26. 26.
    R. L. Willson, in: “Radioprotecters and Anticarcinogens”, O. F. Nygaardand M. G. Simic, eds., Academic Press, New York, p. 1–14 (1983).Google Scholar
  27. 27.
    R. L. Willson, C. A. Dunster, L. G. Forni, C. A. Gee, and K. J. Kitteridge, Phil. Trans. R. Soc. London, B311: 545 (1985).CrossRefGoogle Scholar
  28. 28.
    R. L. Willson, in: “Oxidative Stress”, H. Sies, ed., Academic Press, London, p. 41–72 (1985).Google Scholar
  29. 29.
    K-D. Asmus, in: “Methods in Enzymology”, 105:167 (1984).Google Scholar
  30. 30.
    G. E. Adams and P. Wardman, in: “Free Radicals in Biology”, Academic Press, New York, Vol. 3, p. 53–95 (1977)Google Scholar
  31. 31.
    G. E. Adams, B. D. Michael, and R. L. Willson, “Advances in Chemistry Series” 81: 289 (1968).Google Scholar
  32. 32.
    J. P. Keene, E. J. Land, and A. J. Swallow, in: “Pulse Radiolysis”, M. Ebert, J. P. Keene, A. J. Swallow and J. H. Baxendale, eds.,Academic Press, London, p. 227–245 (1965).Google Scholar
  33. 33.
    R. L. Willson, Chemical Commun., 1425 (1970).Google Scholar
  34. 34.
    K-D. Asmus, H. Möckel, and A. Henglein, J. Phys. Chem., 77: 1218 (1973).CrossRefGoogle Scholar
  35. 35.
    G. E. Adams and R. L. Willson, J. Chem. Soc. Faraday Trans. 1., 69: 719 (1973).CrossRefGoogle Scholar
  36. 36.
    R. L. Willson, Trans. Farad. Soc., 67: 3008 (1971).CrossRefGoogle Scholar
  37. 37.
    K. B. Patel and R. L. Willson, J. Chem. Soc. Faraday Trans. 1, 69: 814 (1973).Google Scholar
  38. 38.
    L. G. Forni and R. L. Willson, Methods in Enzymology, 105: 179 (1984).CrossRefGoogle Scholar
  39. 39.
    J. A. Farrington, E. J. Land, and A. J. Swallow, Biochim. Biophys. Acta, 590: 273 (1980).CrossRefGoogle Scholar
  40. 40.
    R. F. Anderson, Biochim. Biophys. Acta, 590: 277 (1980).CrossRefGoogle Scholar
  41. 41.
    P. M. Wood, FEBS Letts., 44: 22 (1974).CrossRefGoogle Scholar
  42. 42.
    P. Wardman, J. Phys. Chem. Reference Data, 18: 1637 (1989).CrossRefGoogle Scholar
  43. 43.
    J. E. Packer, T. F. Slater, and R. L. Willson, Life Sciences, 23: 2617 (1978).CrossRefGoogle Scholar
  44. 44.
    J. E. Packer and R. L. Willson, D. Bahnemann, and K-D. Asmus, J. Chem. Soc., Perkin Trans. 2, 296 (1980).CrossRefGoogle Scholar
  45. 45.
    J. Mönig, D. Bahnemann, and K-D. Asmus, Chem. Biol. Interact., 47: 15 (1983).CrossRefGoogle Scholar
  46. 46.
    D. Bahnemann, K-D. Asmus, and R. L. Willson, J. Chem. Soc. Perkin Trans. 2, 1661 (1983).Google Scholar
  47. 47.
    D. Bahnemann, K-D. Asmus, and R. L. Willson, J. Chem. Soc. Perkin Trans. 2, 1669 (1983).Google Scholar
  48. 48.
    D. Bahnemann, K-D. Asmus, and R. L. Willson, J. Chem. Soc. Perkin Trans. 2, 890 (1981).Google Scholar
  49. 49.
    I. Wilson, P. Wardman, G. M. Cohen, and M, D’Arcy Doherty, Biochem. Pharmacol., 35: 21 (1986).CrossRefGoogle Scholar
  50. 50.
    L. G. Forni, V. O. Mora-Arellano, J. E. Packer, and R. L. Willson, J. Chem. Soc. Perkin Trans. 2, 1579 (1988).Google Scholar
  51. 51.
    R. H. Bisby, S. Ahmed, R. B. Cundall, and E. W. Thomas, Free Radical Res. Commun., 1: 257 (1986).CrossRefGoogle Scholar
  52. 52.
    M. J. Davies, L. G. Forni, and R. L. Willson, Biochem J., 255: 513 (1988).Google Scholar
  53. 53.
    M. J. Thomas and B. H. J. Bielski, J. Amer. Chem. Soc., 111: 3315 (1989).CrossRefGoogle Scholar
  54. 54.
    S. Steenken, J. Phys. Chem., 83: 595 (1979).CrossRefGoogle Scholar
  55. 55.
    B. S. Wolfenden and R. L. Willson, J. Chem. Soc. Perkin Trans. 2, 805 (1982).Google Scholar
  56. 56.
    L. G. Forni and R. L. Willson, Biochem. J., 240: 905 (1986).Google Scholar
  57. 57.
    L. G. Forni and R. L. Willson, Biochem. J., 240: 897 (1986).Google Scholar
  58. 58.
    J. L. Redpath and R. L. Willson, Int. J. Radiat. Biol., 23: 51 (1973).CrossRefGoogle Scholar
  59. 59.
    L. G. Forni and R. L. Willson, in: “Protective Agents in Cancer”, D. C. H. McBrien and T. F. Slater, eds., Academic Press, London, p. 159–173 (1983).Google Scholar
  60. 60.
    L. G. Forni, J. Mönig, V. O. Mora-Arellano, and R. L. Willson, J. Chem. Soc. Perkin Trans. 2, 961 (1983).Google Scholar
  61. 61.
    C. A. Dunster and R. L. Willson, Int. J. Radiat. Biol., 55: 873 (1989).Google Scholar
  62. 62.
    M. D’Aquino, C. A. Dunster, and R. L. Willson, Biochem. Biophys. Res. Commun., 161: 1199 (1989).CrossRefGoogle Scholar
  63. 63.
    N. V. Raghavan, P. K. Das, and K. Bobrowski, J. Amer. Chem. Soc., 103: 4569 (1984).CrossRefGoogle Scholar
  64. 64.
    C. A. Dunster and R. L. Willson, to be published.Google Scholar
  65. 65.
    R. L. Willson, in: “Iron Metabolism”, R. Porter and D. W. Fitzsimons, eds., Ciba Foundation Symposium, Vol. 51, Elsevier/Excerpts Medica, pp. 331–354 (1977) and references cited.Google Scholar
  66. 66.
    G. Saez, P. J. Thornalley, H. A. O. Hill, R. Hems, and J. V. Bannister, Biochim. Biophys. Acta, 719: 24 (1982).CrossRefGoogle Scholar
  67. 67.
    A. J. F. Searle and R. L. Willson, Biochem. J., 212: 549 (1983).Google Scholar
  68. 68.
    C. Malvy, C. Paoletti, A. J. F. Searle, and R. L. Willson, Biochem. Biophys. Res. Commun., 95: 734 (1980).CrossRefGoogle Scholar
  69. 69.
    L. S. Harman, D. K. Carver, J. Schreiber, and R. P. Mason, J. Biol. Chem., 261: 1642 (1986).Google Scholar
  70. 70.
    T. E. Eling, J. F. Curtis, L. S. Harman, and R. P. Mason, J. Biol. Chem., 261: 5023 (1986).Google Scholar
  71. 71.
    R. L. Willson, K-D. Asmus, and P. Wardman, Nature, 252: 323 (1974).CrossRefGoogle Scholar
  72. 72.
    P. O’Neill, Radiat. Res., 96: 198 (1983).CrossRefGoogle Scholar
  73. 73.
    R. L. Willson, Int. J. Radiat. Biol., 17: 349 (1970).CrossRefGoogle Scholar
  74. 74.
    G. E. Adams and R. L. Willson, Trans. Faraday Soc., 65: 2981 (1969).CrossRefGoogle Scholar
  75. 75.
    M. Tamha, G. Simone, and M. Quintiliani, Int. J. Radiat. Biol., 50: 495 (1986).Google Scholar
  76. 76.
    J. Mönig, K-D. Asmus, L. G. Forni, and R. L. Willson, Int. J. Radiat. Biol., 52: 589 (1987).CrossRefGoogle Scholar
  77. 77.
    A. J. Searle and A. Tomasi, J. Inorg. Biochem., 17: 161 (1982).CrossRefGoogle Scholar
  78. 78.
    M. J. Davies, L. G. Forni and S. L. Shuter, Chem.-Biol. Interact., 61: 177 (1987).CrossRefGoogle Scholar
  79. 79.
    F. Haber and R. Willstätter, Chem. Berichte, 64: 2844 (1931).Google Scholar

Copyright information

© Plenum Press, New York 1990

Authors and Affiliations

  • Christina Dunster
    • 1
  • Robin L. Willson
    • 1
  1. 1.Biology and Biochemistry Dept.Brunel University of West LondonUxbridge, MiddlesexUK

Personalised recommendations