Electron Transfer. 132. Oxidations with Peroxynitrite 1

Inorganic Chemistry

Volumn 35, Issue 26, 1996, Pages 7892-7896

  Al Ajlouni, Ahmad M ^a   Gould, Edwin S ^a  

^a KENT STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000851517     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic960504r     Document Type: Article

References (44)

1. Sponsorship of this work by the National Science Foundation (Grant 9414113) is gratefully acknowledged.
2. Review: Stamler, J. S.; Singel, D. J.; Loscalzo, Science 1992, 258, 1898.
3. See, for example: (a) Fridovich, I. Adv. Inorg. Biochem. 1979, 67, 1. (b) Fee, J. A.; Valentine, J. S. In Superoxide and Superoxide Dismutase, Michelson, A. M., McCord, J. M., Fridovich, I., Eds.; Academic Press: New York, 1979; p 19.
4. See, for example: (a) Fridovich, I. Adv. Inorg. Biochem. 1979, 67, 1. (b) Fee, J. A.; Valentine, J. S. In Superoxide and Superoxide Dismutase, Michelson, A. M., McCord, J. M., Fridovich, I., Eds.; Academic Press: New York, 1979; p 19.
5. Radi, R.; Cosgrove, T. P.; Beckman, J. S.; Freeman, B. A. Biochem. J. 1993, 290, 51.
6. See, for example: Valentine, J. S.; de Freitas, D. M. J. Chem. Educ. 1985, 62, 990.
7. Huie, R. E.; Padmaja, S. Free Radical Res. Commun. 1993, 10, 221.
8. Logager, T.; Sehested, K. J. Phys. Chem. 1993, 97, 6664.
9. (a) Beckman, J. S.; Chen, J.; Ischiropoulos, H.; Crow, J. P. Methods Enzymol. 1994, 233, 229.
10. (b) Tsai, J.-H. M.; Harrison, J. G.; Martin, J. C.; Hamilton, T. P.; van der Woerd, M.; Jablonsky, M. J.; Beckman, J. S. J. Am. Chem. Soc. 1994, 116, 4115.
11. Zhu, L.; Gunn, C.; Beckman, J. S. Arch. Biochem. Biophys. 1992, 298, 452.
12. Ischiropoulos, H.; Zhu, L.; Beckman, J. S. Arch. Biochem. Biophys. 1992, 298, 446.
13. Hogg, N.; Joseph, J.; Kalyanaraman, Arch. Biochem. Biophys. 1994, 314, 153.
14. Steinberg, D.; Parathasarthy, S.; Carew, T. E.; Khoo, J. C.; Witztum, J. L. N. Engl. J. Med. 1989, 320, 915.
15. See, for example: (a) Hughes, M. N.; Nicklin, H. G. J. Chem. Soc. A 1970, 925. (b) Hughes, M. N.; Nicklin, H. G.; Sackrule, W. A. C. J. Chem. Soc. A, 1971, 3722. (c) Benton, D. J.; Moore, P. J. Chem. Soc. A 1970, 3179. (d) Anbar, M.; Taube, H. J. Am. Chem. Soc. 1954, 76, 6243. (e) Shuali, U.; Ottolenghi, M.; Rabain, J.; Helin, Z. J. Phys. Chem. 1969, 73, 3445.
16. See, for example: (a) Hughes, M. N.; Nicklin, H. G. J. Chem. Soc. A 1970, 925. (b) Hughes, M. N.; Nicklin, H. G.; Sackrule, W. A. C. J. Chem. Soc. A, 1971, 3722. (c) Benton, D. J.; Moore, P. J. Chem. Soc. A 1970, 3179. (d) Anbar, M.; Taube, H. J. Am. Chem. Soc. 1954, 76, 6243. (e) Shuali, U.; Ottolenghi, M.; Rabain, J.; Helin, Z. J. Phys. Chem. 1969, 73, 3445.
17. See, for example: (a) Hughes, M. N.; Nicklin, H. G. J. Chem. Soc. A 1970, 925. (b) Hughes, M. N.; Nicklin, H. G.; Sackrule, W. A. C. J. Chem. Soc. A, 1971, 3722. (c) Benton, D. J.; Moore, P. J. Chem. Soc. A 1970, 3179. (d) Anbar, M.; Taube, H. J. Am. Chem. Soc. 1954, 76, 6243. (e) Shuali, U.; Ottolenghi, M.; Rabain, J.; Helin, Z. J. Phys. Chem. 1969, 73, 3445.
18. See, for example: (a) Hughes, M. N.; Nicklin, H. G. J. Chem. Soc. A 1970, 925. (b) Hughes, M. N.; Nicklin, H. G.; Sackrule, W. A. C. J. Chem. Soc. A, 1971, 3722. (c) Benton, D. J.; Moore, P. J. Chem. Soc. A 1970, 3179. (d) Anbar, M.; Taube, H. J. Am. Chem. Soc. 1954, 76, 6243. (e) Shuali, U.; Ottolenghi, M.; Rabain, J.; Helin, Z. J. Phys. Chem. 1969, 73, 3445.
19. See, for example: (a) Hughes, M. N.; Nicklin, H. G. J. Chem. Soc. A 1970, 925. (b) Hughes, M. N.; Nicklin, H. G.; Sackrule, W. A. C. J. Chem. Soc. A, 1971, 3722. (c) Benton, D. J.; Moore, P. J. Chem. Soc. A 1970, 3179. (d) Anbar, M.; Taube, H. J. Am. Chem. Soc. 1954, 76, 6243. (e) Shuali, U.; Ottolenghi, M.; Rabain, J.; Helin, Z. J. Phys. Chem. 1969, 73, 3445.
20. Edwards, J. O.; Plumb, R. C. Prog. Inorg. Chem. 1994, 41, 599. This review emphasizes the photochemistry of peroxynitrite and its transformations with inorganic coreagents.
21. Koppenol, W. H. J.; Moreno, J. J.; Pryor, W. A.; Ischiropoulos, H.; Beckman, J. S. Chem. Res. Toxicol 1992, 4, 834.
22. See, for example: (a) Sosnovsky, G.; Rawlinson, D. J. In Organic Peroxides, Vol. II; Swern, D., Ed.; Wiley: New York, 1971; pp 153-268. (b) Johnson, N. A.; Gould, E. S. J. Am. Chem. Soc. 1973, 95, 5198.
23. See, for example: (a) Sosnovsky, G.; Rawlinson, D. J. In Organic Peroxides, Vol. II; Swern, D., Ed.; Wiley: New York, 1971; pp 153-268. (b) Johnson, N. A.; Gould, E. S. J. Am. Chem. Soc. 1973, 95, 5198.
24. See, for example: Su, C.-C; Reed, J. W.; Gould, E. S. Inorg. Chem. 1973, 12, 337.
25. Goldstein, S.; Czapski, G. Inorg. Chem. 1995, 34, 4041.
26. Radi, R.; Beckman, J. S.; Bush, K. M.; Freeman, B. A. J. Biol. Chem. 1991, 266, 4244.
27. Pryor, W. A.; Jin, X.; Squadrito, G. L. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 11173.
28. Beckman, J. S.; Beckman, T. W.; Chen, J.; Marshall, P. A.; Freeman, B. A. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 1620.
29. Ischiropoulos, H.; Zhu, L.; Chen, M.; Tsai, M.; Martin, J. C.; Smith, C. D.; Beckman, J. B. Arch. Biochem. Biophys. 1992, 298, 431.
30. Halfpenny, E.; Robinson, P. L. J. Chem. Soc. A 1952, 928.
31. Both nitrite and nitrate were shown to be without significant effect on the stoichiometry and kinetics of the oxidations examined here when these anions were present at concentrations comparable to, or less than, that of peroxynitrite.
32. Swift, E. H. A System of Chemical Analysis; Prentice-Hall: Englewood Cliffs, NJ, 1938; p 277.
33. 3). Since, however, redox reactions are generally favored by protonation of the oxidant and deprotonation of the reductant (rather than the reverse), the alternate combination may be assumed to predominate greatly.
34. Martell, A. E.; Smith, R. M. Critical Stability Constants; Plenum: New York, 1976; Vol. 4, p 132.
35. (a) Gress, M. E.; Jacobson. Inorg. Chim. Acta 1974, 8, 209.
36. (b) For an earlier study of aqueous solutions of this complex, see: Anderegg, G.; Malik, S. Helv. Chim. Acta 1970, 53, 577.
37. Richlen, H.; Hezel, E. Justus Liebigs Ann. Chem. 1931, 487, 213.
38. (a) Holm, R. H. Chem. Rev. 1987, 87, 1401.
39. (b) Holm, R. H.; Donahue, J. P. Polyhedron 1993, 12, 571.
40. II(pH 11), -0.67V.
41. II(pH 11), -0.67V.
42. Jhanji, A. K.; Gould, E. S. Int. J. Chem. Kinet. 1991, 23, 229.
43. See, for example: Kolbe, K. E.; Hellwig, K. C. Ind. Eng. Chem. 1955, 47, 1116.
44. With respect to our eq 16, a reviewer asks why we favor transfer of the "terminal" rather the internal oxygen of peroxynitrous acid. Since the transferred oxygen is acting in an electrophilic capacity, its action should be favored by protonation. Moreover, breakage in the manner indicated is consistent with the formation of nitrite.