Superoxide Chemistry in Non-Aqueous Media

  • Aryeh A. Frimer
Part of the Basic Life Sciences book series (BLSC, volume 49)

Abstract

The focal role played by molecular oxygen and oxygen species in living systems seems to have been realized almost from the very discovery of oxygen more than two centuries ago.1 The continuing interest in oxygen stems from the complicated role it plays not only in the “breath of life” but also more interestingly in oxygen toxicity — what might poetically be called the “breath of death.” One of the active oxygen species implicated in this detrimental process is the ubiquitous one-electron reduction product of molecular oxygen, superoxide anion radical2–4, O2.

Keywords

Pyridine Ketone Styrene Indole Hydroperoxide 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    A. A. Frimer and I. Rosenthal in Foreword to “Active Oxygen — Part A”, Israel J. Chem., 23:398 (1983).Google Scholar
  2. 2.
    See the articles of I. Fridovich and J. Fee and the subsequent discussion in “Oxygen and Oxy-Radicals in Chemistry and Biology”, M. A. J. Rodgers and E. L. Powers, Eds., Academic Press, New York (1981), pp. 197–239.Google Scholar
  3. 3.
    See the exchange of correspondence between I. Fridovich, and D. T. Sawyer and J. S. Valentine, Accounts Chem. Res., 15:200 (1982).CrossRefGoogle Scholar
  4. 4.
    R. M. Baum, Superoxide theory of oxygen toxicity is center of heated debate, Chem. Eng. News April 9, 1984 p.20–26 and subsequent Letters to the Editor on June 4, 1984, p.50 and July 2, 1984, p.47.Google Scholar
  5. 5.
    Comments of I. Fridovich in J. D. Spikes and H. M. Swartz, International conference on singlet oxygen and related species in chemistry and biology — review and general discussion, Photochem. Photobiol., 28:921 (1978).CrossRefGoogle Scholar
  6. 6.
    B. H. J. Bielsky, Reevaluation of the spectral and kinetic properties of HO2 and O2 free radicals, Photochem. Photobiol., 28:645 (1978).CrossRefGoogle Scholar
  7. 7.
    A. D. Goolsby and D. T. Sawyer, The electrochemical reduction of superoxide ion and the oxidation of hydroxide ion in dimethyl-sulfoxide, Anal. Chem., 40:83 (1968).CrossRefGoogle Scholar
  8. 8.
    A. D. T. Sawyer and M. J. Gibian, The chemistry of superoxide ion, Tetrahedron, 35:1471 (1979);CrossRefGoogle Scholar
  9. 8a.
    b. J. Wilshire and D. T. Sawyer, Redox chemistry of dioxygen species, Accounts Chem. Res., 12:105 (1979).CrossRefGoogle Scholar
  10. 9.
    S. Torii, The new role of electroreductive mediators in electroorganic synthesis, Synthesis, 873 (1986); see especially 883 ff.Google Scholar
  11. 10.
    A. D. McElroy and J. S. Hasman, Synthesis of tetramethylammonium Superoxide, Inorg. Chem., 40:1798 (1964).CrossRefGoogle Scholar
  12. 11.
    J. W. Peters and C. S. Foote, Chemistry of superoxide ion. II. Reaction of hydroperoxides, J. Amer. Chem. Soc., 98:873 (1976).CrossRefGoogle Scholar
  13. 12.
    J. S. Valentine and A. B. Curtis, A convenient preparation of solutions of superoxide anion and the reaction of superoxide anion with a copper (II) complex, J. Amer. Chem. Soc., 97:224 (1975).CrossRefGoogle Scholar
  14. 13.
    A. A. Frimer, T. Farkash-Solomon and G. Aljadeff, The Mechanism of the superoxide anion radical [O2 ‘] mediated oxidation of diaryl-methanes, J. Org. Chem., 51:2093 (1986).CrossRefGoogle Scholar
  15. 14.
    A. Streitweiser and C. H. Heathcock,“Introduction to Organic Chemistry”, Collier Macmillan, N.Y. (1976), appendix IV, p.1190.Google Scholar
  16. 15.
    I. Rosenthal and A. A. Frimer, The reaction between tetracyclone and superoxide anion radical, Tetrahedron Lett., 3731 (1975).Google Scholar
  17. 16.
    R. L. Arudi, A. D. Allen and B. H. J. Bielski, Some observations on the chemistry of KO2 — DMSO solutions, FEBS Lett., 35:265 (1981).CrossRefGoogle Scholar
  18. 17.
    N. Kornblum and S. Singaram, Conversion of nitriles to amides and esters to acids by the action of sodium superoxide, J. Org. Chem. 44:4727 (1979).CrossRefGoogle Scholar
  19. 18.
    K. Shibata, Y. Saito, K. Urano and M. Matsui, Reactions of Schiff bases with superoxide ion in acetonitrile, Bull. Chem. Soc. Japan, 59:3323 (1986).CrossRefGoogle Scholar
  20. 19.
    M. Tezuka, H. Hamada, Y. Ohkatsu and T. Osa, Reactivity of electrogenerated superoxide ion. II. Correlation between stability and reactivity of superoxide ion, Denki Kagaku, 44:17 (1976).Google Scholar
  21. 20.
    Y. Sawaki and Y. Ogata, Mechanism of the reaction of nitriles with alkaline hydrogen peroxide. Reactivity of peroxycarboximidic acid and application to superoxide ion reaction, Bull. Chem. Soc. Japan 54:793 (1981).CrossRefGoogle Scholar
  22. 21.
    S. Oae, T. Takata and Y. H. Kim, Reaction of organic sulfur compounds with hyperoxide anion (0 ‘). IV. Evidence for formation of peroxy sulfur intermediates: oxidation of sulfoxides, phosphines and olefins with intermediary peroxysulfur species, Bull. Chem. Soc. Japan. 54:2712 (1981).CrossRefGoogle Scholar
  23. 22.
    E. Balogh-Hergovich and G. Speier, Ring cleavage and ring expansion of indoles by superoxide ion, Tetrahedron Lett. 23:4473 (1982).CrossRefGoogle Scholar
  24. 23.
    E. Balogh-Hergovich and G. Speier, The reactions of indoles with superoxide ion, Oxidat. Commun., 4:337 (1983);Google Scholar
  25. 24.
    M. M. A. El-Sukkary and G. Speier, Oxygenation of 3-hydroxyflavones by superoxide anion, J. Chem. Soc. Chem. Commun., 745 (1981) and G. Speier, personal communication (1984).Google Scholar
  26. 25.
    A. Le Berre and Y. Berguer, Reactions des superoxydes alcalins avec des composes organiques. I. Reactions radicalaires, Bull. Soc. Chim. Fr., 2363 (1966); see especially the second footnote to Table II.Google Scholar
  27. 26.
    J. L. Roberts, Jr., T. C. Calderwood, and D. T. Sawyer, Oxygenation by superoxide ion of CCl4, FCCl3, HCCl3 P,P’-DDT, and related trichloromethyl substrates (RCCl3) in aprotic solvents, J. Amer. Chem. Soc., 105:7691 (1983).CrossRefGoogle Scholar
  28. 27.
    S. T. Parrington and G. B. Kenion, Superoxide: base, nucleophile, radical or electron transfer reagent, J. Chem. Soc., Chem. Commun., 731 (1982).Google Scholar
  29. 28.
    J. R. Kanofsky, Singlet oxygen production in superoxide ion — halocarbon systems, J. Amer. Chem. Soc., 108:2977 (1986).CrossRefGoogle Scholar
  30. 29.
    C.A. Long and B. H. J. Bielsky, Rate of reaction of superoxide radical with chloride-containing species, J. Phys. Chem., 84:555 (1980).CrossRefGoogle Scholar
  31. 30.
    D. K. Akutagawa, N. Furukawa and S. Oae, Oxidation of S,S-Diaryl-N-(p-tolylsulfonyl)sulfilimines and N-unsubstituted S,S-diaryl-sulfil-imines with potassium hvperoxide anion radical (O2 ) in the presence of l-bromopropane, benzoyl chloride, carbon tetrachloride, chloroform or dichloromethane in aprotic media, Bull. Chem. Soc. Japan 57:1104 (1984).CrossRefGoogle Scholar
  32. 31.
    A. A. Frimer, The organic chemistry of superoxide anion radical, in “The Chemistry of Functional Groups: Peroxides”, S. Patai, ed., Wiley, Chichester (1983) pp 429–461.Google Scholar
  33. 32.
    A. A. Frimer, Organic reactions involving the superoxide anion, in “Superoxide Dismutase”, L. W. Oberley ed., Chemical Rubber Co., Boca Raton, FL. (1982), Vol. 2, pp 83–125.Google Scholar
  34. 33.
    J. A. Fee and J.S. Valentine. Chemical and physical properties of superoxide, in “Superoxide and Superoxide Dismutase”, A. M. Michelson, J. M. McCord and I. Fridovich eds., Academic Press, N.Y. (1977) p.19.Google Scholar
  35. 34.
    D. T. Sawyer and E. J. Nanni, Jr., Redox chemistry of O2 and peroxides, in “Oxygen and oxy-radicals in chemistry and biology,” M. A. J. Rodgers and E. L. Powers, eds., Academic Press, N.Y. (1981) p.15–44.Google Scholar
  36. 35.
    J. Chevalet, F. Rouelle, L. Gierst and J. P. Lambert, Electrogeneration and some properties of superoxide ion in aqueous solutions, J. Electroanal. Chem., 39:201 (1972).CrossRefGoogle Scholar
  37. 36.
    R. Dietz, M. E. Peover and P. Rothbaum, Electrode reactions of organic compounds with electrochemically generated O2 ion, Chem. Ing. Tech. 42:185 (1970).CrossRefGoogle Scholar
  38. 37.
    M. S. McDavell, J. H. Espenson and A. Bakac, Kinetics of aqueous outersphere electron-transfer reactions of superoxide ion. Implications concerning 02/02 self exchange rate constant, Inorg. Chem., 23:2232 (1984).Google Scholar
  39. 38.
    W. H. Koppenol, Thermodynamics of the Fenton-driven Haber-Weiss and related reactions in “Oxy-Radicals and their Scavenger Systems”, G. Cohen and R. A. Greenwald, eds., Elsevier, New York (1983) Vol. I, pp 84–88.Google Scholar
  40. 39.
    See however, A.R. Forrester and V. Purushotham, Mechanism of reactions of carboxylic acid derivatives with superoxide, hydrolysis of esters by superoxide, J. Chem. Soc. Chem. Commun. 1505 and J. Chem. Soc. Perkin I, 945 (1987) who present evidence for an electron transfer mechanism in the superoxide mediated “saponification” of o-phenylbenzoyl peroxide.Google Scholar
  41. 40.
    A. A. Frimer and I. Rosenthal, Chemical reactions of superoxide anion radical in aprotic solvents, Photochem. Photobiol., 28:711 (1978).CrossRefGoogle Scholar
  42. 41.
    See however, D. T. Sawyer, J. J. Stamp and K. A. Menton, Reactivity of superoxide ion with ethyl pyruvate, α-diketones and benzil in DKF, J. Org. Chem., 48:3733 (1983) who suggest a nucleophilic addition by O2 .CrossRefGoogle Scholar
  43. 42.
    See discussion in J. L. Roberts and D. T. Sawyer, Activation of Superoxide ion by reactions with protons, electrophiles, secondary amines, radicals, and reduced metal ions, Israel J. Chem. 23:430 (1983).Google Scholar
  44. 43.
    D. C. Neckers and G. Hauck, Reactions of diphenylcyclopropenone and tetracyclones with potassium superoxide, J. Org. Chem., 48:4691 (1983).CrossRefGoogle Scholar
  45. 44.
    See however, M. Gareil, J. Pinson and J. M. Saveant. Nucleophilic substitution of aromatic halides by electrogenerated superoxide ions, Nouveau J. Chim., 5:311 (1981) who suggest a nucleophilic addition by O2 .Google Scholar
  46. 45.
    M. J. Gibian and S. Russo, Electron transfer between superoxide ion and an α,β-unsaturated ketone, J. Org. Chem. 49:4304 (1984).CrossRefGoogle Scholar
  47. 46.
    E. J. Corey, M. M. Mehrotra and A. U. Khan, Antiarthritic gold compounds effectively quench electronically excited singlet oxygen, Science, 236:68 (1987).PubMedCrossRefGoogle Scholar
  48. 47.
    W. C. Danen and R. L. Arudi, Generation of singlet oxygen in the reaction of superoxide anion radical with diacyl peroxides, J. Amer. Chem. Soc., 100:3944 (1978).CrossRefGoogle Scholar
  49. 48.
    A. U. Khan, Direct spectral evidence of the generation of singlet molecular oxygen (IΔg) in the reaction of potassium superoxide with water, J. Amer.Chem. Soc., 103:6516 (1981).CrossRefGoogle Scholar
  50. 49.
    The original kinetic studies were carried out in DMSO, whose problematic nature we have discussed. Nevertheless, two runs were repeated in pyridine with similar results; See reference 6a Table 1.Google Scholar
  51. 50.
    I. M. Goldstein and G. Weissmann, Effects of the generation of superoxide anion on permeability of liposomes, Biochem. Biophys. Res. Commun., 75:604 (1977).PubMedCrossRefGoogle Scholar
  52. 51.
    D. -H. Chin, G. Chiercato, Jr., E. J. Nanni, Jr., and D. T. Sawyer Proton-induced disproportionation of superoxide ion in aprotic media, J. Am. Chem. Soc., 104:1296 (1982).CrossRefGoogle Scholar
  53. 52.
    J. P. Stanley, Reactions of superoxides and peroxides, J. Org. Chem., 45:1413 (1980).CrossRefGoogle Scholar
  54. 53.
    A. A. Frimer, G. Aljadeff and P. Gilinsky-Sharon, Reaction of coumarins with superoxide anion radical: facile entry to o-coumarinic acid systems, Israel J. Chem., 27:39 (1986).Google Scholar
  55. 54.
    A. A. Frimer, P. Gilinsky-Sharon, J. Hameiri and G. Aljadeff, Superoxide-, tert-butoxide-, and hydroxide-mediated autoxidation of 3-oxo-Δ4-steroids in aprotic media, J. Org. Chem., 47:2818 (1982).CrossRefGoogle Scholar
  56. 55.
    S. Matsumoto, M. Matsuo and Y. Iitaka, Oxygenations of Vitamin E (α-tocopherol) and its model compound in the presence of potassium superoxide suspended in THF and unusual acyloin rearrangements, J. Org. Chem. 51:1435 (1986).CrossRefGoogle Scholar
  57. 56.
    A. A. Frimer, G. Aljadeff and J. Ziv, Reaction of (arylmethyl) amines with superoxide anion radical in aprotic media. Insights into cytokynin senescence inhibition, J. Org. Chem. 48:1700 (1983).CrossRefGoogle Scholar
  58. 57.
    D. T. Sawyer, T. S. Calderwood, C. L. Johlman and C. I. Wilkins, Oxidation by superoxide ion of catechols, ascorbic acid, dihydro-phenazine and reduced flavins to their respective anion radicals. A common mechanism via a sequential proton-hydrogen atom transfer, J. Org. Chem., 50:1409 (1985) and references cited therein.Google Scholar
  59. 58.
    C. J. M. Fukuto, E. W. DiStefano, J. N. Burstyn, J. S. Valentine and A. K. Cho, Mechanism of oxidation of N-hydroxyphentermine by superoxide, Biochemistry 24:4161 (1985).PubMedCrossRefGoogle Scholar
  60. 59.
    I. B. Afanas’ev, V. V. Grabovetskii and N. S. Kuprianova, Kinetics and mechanism of the reactions of superoxide in solution. Part 5. Kinetics and mechanism of the interaction of superoxide with Vitamin E and ascorbic acid, J. Chem. Soc. Perkin II, 281 (1987).Google Scholar
  61. 60.
    J. F. Liebman and J. S. Valentine, Concerning the radical character of superoxide. The H-O bond energy of HO2. Israel J. Chem., 23:439 (1983).Google Scholar
  62. 61.
    G. Feroci and S. Roffia, Study of the reactions between styrene and electrogenerated superoxide ion in dimethylformamide, J. Electro-anal. Chem. 81:387 (1977).CrossRefGoogle Scholar
  63. 62.
    A. A. Frimer, J. Hameiri-Buch and G. Aljadeff, unpublished results (1987).Google Scholar

Copyright information

© Plenum Press, New York 1988

Authors and Affiliations

  • Aryeh A. Frimer
    • 1
  1. 1.Department of ChemistryBar-Ilan UniversityRamat-GanIsrael

Personalised recommendations