ENDOR studies of alkyl substituted p-Benzosemiquinones in reversed micelles and in 2-propanol

  • B. Kirste
  • D. Niethammer
  • P. Tian
  • H. Kurreck


Various substituted p-benzosemiquinone radical anions, inter alia ubisemiquinone and derivatives, have been investigated in 2-propanol and in reversed micelles by EPR and ENDOR spectroscopy. Unsymmetrical semiquinones, with respect to the oxygen atoms, experience remarkable hyperfine shifts depending on the medium. This effect even allows differentiation between stereoisomers. Immobilization of the semiquinone molecules at the water-surfactant interface in reversed micelles gives rise to pronounced asymmetric linewidth effects. In the case of 2-cyclohexyl-3-methyl-1,4-benzosemiquinones, mixtures of two species (conformers) have been observed.


  1. [1]
    Trumpower B.L. (ed.): Function of Quinones in Energy Conserving Systems. New York: Academic Press 1982.Google Scholar
  2. [2]
    Boxer S.G.: Biochim. Biophys. Acta726, 265 (1983); Wasielewski M.R.: Photochem. Photobiol.47, 923 (1988); von Gersdorff J., Huber M., Schubert H., Niethammer D., Kirste B., Plato M., Möbius K., Kurreck H., Eichberger R., Kietzmann R., Willig F.: Angew. Chem.102, 690 (1990); Angew. Chem., Int. Ed. Engl.29, 670 (1990); Lendzian F., Schlüpmann J., von Gersdorff J., Möbius K., Kurreck H.: Angew. Chem. (in press).Google Scholar
  3. [3]
    Niethammer D., Kirste B., Kurreck H.: J. Chem. Soc., Faraday Trans.86, 3191 (1990)CrossRefGoogle Scholar
  4. [4]
    Luisi P.L.: Angew. Chem.97, 449, (1985); Angew. Chem., Int. Ed. Engl.24, 439 (1985)CrossRefGoogle Scholar
  5. [5]
    Jacobsen N., Torssell K.: Justus Liebigs Ann. Chem.763, 135 (1972)CrossRefGoogle Scholar
  6. [6]
    Dieks H., Kurreck H.: to be published.Google Scholar
  7. [7]
    Langlais M., Buzas A., Freon P.: C. R. Hebd. Séances Acad. Sci.254, 1452 (1962)Google Scholar
  8. [8]
    Kurreck H., Kirste B., Lubitz W.: Angew. Chem.96, 171 (1984); Angew. Chem., Int. Ed. Engl.23, 173 (1984)CrossRefGoogle Scholar
  9. [9]
    Kurreck H., Kirste B., Lubitz W. in: Electron Nuclear Double Resonance Spectroscopy of Radicals in Solution. New York: VCH Publishers 1988.Google Scholar
  10. [10]
    Kirste B.: J. Magn. Reson.73, 213 (1987)Google Scholar
  11. [11]
    Nelder J.A., Mead R.: Computer J.7, 308 (1965); Beckwith A.L.J., Brumby S.: J. Magn. Reson.73, 252 (1987)MATHGoogle Scholar
  12. [12]
    Marquardt D.W., Bennett R.G., Burrell E.J.: J. Mol. Spectrosc.7, 269 (1961); Marquardt D.W.: J. Soc. Ind. Appl. Math.11, 431 (1963)CrossRefADSGoogle Scholar
  13. [13]
    Sullivan P.D., Bolton J.R., Geiger W.E. Jr.: J. Am. Chem. Soc.92, 4176 (1970)CrossRefGoogle Scholar
  14. [14]
    Lazdins D., Karplus M.: J. Am. Chem. Soc.87, 920 (1965)CrossRefGoogle Scholar
  15. [15]
    Lim Y.Y., Fendler J.H.: J. Am. Chem. Soc.100, 7490 (1978)CrossRefGoogle Scholar
  16. [16]
    Barelli A., Eicke H.-F.: Langmuir2, 780 (1986)CrossRefGoogle Scholar
  17. [17]
    Häring G., Luisi P.L., Hauser H.: J. Phys. Chem.92, 3574, (1988)CrossRefGoogle Scholar
  18. [18]
    Kotake Y., Janzen E.G.: J. Phys. Chem.92, 6357, (1988)CrossRefGoogle Scholar
  19. [19]
    Nordio P.L. in: Spin Labeling. Theory and Applications (Berliner L.J. ed.), vol. 1, p. 5. New York: Academic Press, Inc. 1976.Google Scholar
  20. [20]
    Freed J.H., Fraenkel G.K.: J. Chem. Phys.39, 326 (1963)CrossRefADSGoogle Scholar
  21. [21]
    Hudson A., Luckhurst G.R.: Chem. Rev.69, 191 (1969)CrossRefGoogle Scholar
  22. [22]
    McConnell H.M., Strathdee J.: Mol. Phys.2, 129 (1959)CrossRefADSGoogle Scholar
  23. [23]
    Heller H.C., McConnell H.M.: J. Chem. Phys.32, 1535 (1960)CrossRefADSGoogle Scholar
  24. [24]
    Das M.R., Connor H.D., Leniart D.S., Freed J.H.: J. Am. Chem. Soc.92, 2258 (1970)CrossRefGoogle Scholar
  25. [25]
    Reference [9],, Chapter 6.Google Scholar
  26. [26]
    Biehl R., Plato M., Möbius K.: J. Chem. Phys.63, 3515 (1975)CrossRefADSGoogle Scholar

Copyright information

© Springer 1992

Authors and Affiliations

  • B. Kirste
    • 1
  • D. Niethammer
    • 1
  • P. Tian
    • 1
  • H. Kurreck
    • 1
  1. 1.Institut für Organische Chemie Freie Universität BerlinBerlin 33Germany

Personalised recommendations