15N CIDNP study of formation and decay of peroxynitric acid: Evidence for formation of hydroxyl radicals

Inorganic Chemistry

Volumn 42, Issue 14, 2003, Pages 4275-4287

  Lehnig, Manfred ^a   Kirsch, Michael ^b   Korth, Hans Gert ^c  

^a TU DORTMUND UNIVERSITY   (Germany)

^b UNIVERSITY HOSPITAL ESSEN   (Germany)

^c UNIVERSITY OF DUISBURG ESSEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON DIOXIDE; HYDROGEN PEROXIDE; HYDROXYL RADICAL; NITRIC ACID DERIVATIVE; PEROXYNITRITE; PEROXYNITROUS ACID;

ARTICLE; CHEMICAL REACTION; DECOMPOSITION; ELECTRON SPIN RESONANCE; ELECTRON TRANSPORT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH; POLARIZATION; QUANTUM CHEMISTRY; SPIN TRAPPING;

EID: 0037898188     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic020650z     Document Type: Article

References (66)

1. Cantrell, C. A. In N-centered Radicals; Agassi, Z. B., Ed.; J. Wiley: Chichester, U.K., 1998; p 371.
2. Wallington, T. J.; Nielsen, O. J. In Peroxyl Radicals; Agassi, Z. B., Ed.; J. Wiley: Chichester, U.K., 1997; p 457.
3. Kenley, R. A.; Trevor, P. L.; Lan, B. Y. J. Am. Chem. Soc. 1981, 103, 2203-2206.
4. D'Ans, J.; Friederich, W. Z. Anorg. Chem. 1911, 73, 325-359.
5. Schwarz, R. Z. Anorg. Chem. 1948, 256, 3-9.
6. Appelman, H.; Gosztola, D. J. Inorg. Chem. 1995, 34, 787-791.
7. Halliwell, B.; Gutteridge, M. C. Free Radicals in Biology and Medicine, 3rd ed.; University Press: Oxford. U.K., 1999; p 99.
8. Kirsch, M.; Lehnig, M.; Korth, H.-G.; Sustmann, R.; de Groot, H. Chem. - Eur. J. 2001, 7, 3313-3320.
9. Kirsch, M.; de Groot, H. J. Biol. Chem. 2000, 275, 16702-16708.
10. Sutton, H. C.; Seddon, W. A.; Sopchyshyn, F. C. Can. J. Chem. 1978, 56, 1961-1964.
11. Lammel, G.; Perner, D.; Warneck, P. J. Phys. Chem. 1990, 94 (4), 6141-6144.
12. Regimbal, J.-M.; Mozurkewich, M. J. Phys. Chem. A 1997, 101, 8822-8829.
13. Goldstein, S.; Czapski, G.; Lind, J.; Merenyi, G. Inorg. Chem. 1998, 37, 3943-3947.
14. Halfpenny, E.; Robinson, P. L. J. Chem. Soc. 1952, 928-938.
15. Hughes, M. N.; Nicklin, H. G. J. Chem. Soc. A 1968, 450-452.
16. Logager, T.; Sehested, K. J. Phys. Chem. 1993, 97, 10047-10052.
17. Hodges, G. R.; Ingold, K. U. J. Am. Chem. Soc. 1999, 121, 10695-10701.
18. Kissner, R.; Koppenol, W. H. J. Am. Chem. Soc. 2002, 124, 234-239.
19. Lymar, S. V.; Hurst, J. K. J. Am. Chem. Soc. 1995, 117, 8867-8868.
20. Coddington, J. W.; Wherland, S.; Hurst, J. K. Inorg. Chem. 2001, 40, 528-532.
21. Thomas, J. K. Adv. Radiat. Chem. 1969, 1, 103-198.
22. Behar, D.; Czapski, G. J.; Duchovny, I. J. Phys. Chem. 1970, 74, 2206-2210.
23. Beckman, J.; Beckman, T. W.; Chen, J.; Marshall, P. A.; Freeman, B. A. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 1620-1624.
24. Ischiropoulos, H.; Zhu, L.; Chen, J.; Tsai, M.; Martin, J. C.; Smith, C. D.; Beckman, J. S. Arch. Biochem. Biophys. 1992, 298, 431-437.
25. Butler, A. R.; Rutherford, T. J.; Short, D. M.; Ridd, J. H. Chem. Commun. 1997, 669-670.
26. Lehnig, M. Arch. Biochem. Biophys. 1999, 368, 303-318.
27. Lehnig, M.; Jakobi, K. J. Chem. Soc., Perkin Trans. 2 2000, 2016-2021.
28. Butler, A. R.; Rutherford, T. J.; Short, D. M.; Ridd, J. H. Nitric Oxide: Biol. Chem. 2000, 4, 472-482.
29. Lehnig, M. Arch. Biochem. Biophys. 2001, 393, 245-254.
30. Bargon, J.; Fischer, H.; Johnsen, U. Z. Naturforsch. 1967, 22A, 1551-1555.
31. Ward, H. R.; Lawler, R. G. J. Am. Chem. Soc. 1967, 89, 5518-5519.
32. Kaptein, R.; Oosterhoff, L. J. Chem. Phys. Lett. 1969, 4, 195-197.
33. Closs, G. L.; Trifunac, A. D. J. Am. Chem. Soc. 1969, 91, 4552-4554.
34. Kaptein, R. Chem. Commun. 1971, 732-733.
35. Clemens, A. H.; Ridd, J. H.; Sandall, J. P. B. J. Chem. Soc., Perkin Trans. 2 1984, 1659-1665.
36. Augusto, O.; Bonini, M. G.; Amanso, A. M.; Linares, E.; Santos, C. C. X.; De Menezes, S. L. Free Radical Biol. Med. 2002, 32, 841-859.
37. Kirsch, M.; Korth, H.-G.; Sustmann, R.; de Groot, H. Biol. Chem. 2002, 383, 389-399.
38. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, A. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N. Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Menucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M.-A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98W, revision A.9; Gaussian: Pittsburgh, PA, 2000.
39. Miller, C. E.; Lynton, J. I.; Keevil, D. M.; Francisco, J. S. J. Phys. Chem. A 1999, 103, 11451-11459.
40. Duling, D. R. WinSim; Laboratory of Molecular Biophysics, NIEHS, NIH: Research Triangle Park, NC. See: Duling, D. R. J. Magn. Reson. B 1994, 105, 105-110.
41. Duling, D. R. WinSim; Laboratory of Molecular Biophysics, NIEHS, NIH: Research Triangle Park, NC. See: Duling, D. R. J. Magn. Reson. B 1994, 105, 105-110.
42. Goldstein, S.; Lind, J.; Merenyi, G. J. Chem. Soc., Dalton Trans. 2002, 808-810.
43. Anbar, M.; Taube, H. J. Am. Chem. Soc. 1984, 76, 6243-6247.
44. Benton, D. J.; Moore, P. J. Chem. Soc. A 1970, 3179-3182.
45. Saha, A.; Goldstein, S.; Cabelli, D.; Czapski, G. Free Radical Biol. Med. 1998, 24, 653-659.
46. Goldstein, S.; Czapski, G. Inorg. Chem. 1997, 36, 4156-4162.
47. Landolt-Börnstein, New Series, Group II. Magnetic Properties of Free Radicals, Vols. 11/17a-h; Fischer, H., Ed.; Springer-Verlag: Berlin, 1987-1990.
48. Stanbury, D. M.; deMaine, M. M.; Goodloe, G. J. Am. Chem. Soc. 1989, 111, 5496-5498.
49. Thomas, K. J. Adv. Radiat. Chem. 1969, 1, 103-198.
50. Schwartz, A.; White, W. H. Adv. Environ. Sci. Technol. 1983, 12, 1-116.
51. Lehnig, M.; Fischer, H. Z. Naturforsch. 1972, 27A, 1300-1307.
52. Barone, V.; Cossi, M.; Tomasi, J. J. Chem. Phys. 1997, 107, 3210-3221.
53. Gonzales, C.; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154-2161.
54. -1; see: Lynch, B. J.; Truhlar, D. G. J. Phys. Chem. A 2001, 105, 2936-2941.
55. Katsumura, J.; Jiang, P. Y.; Nagaishi, R.; Oishu, T.; Ishigure, K.; Yoshida, Y. J. Phys. Chem. 1991, 95, 4435-4439.
56. Morton, J. R.; Preston. K. F.; Strach, S. J. J. Phys. Chem. 1979, 83, 533-535.
57. Kissner, R.; Nauser, Th.; Bugnon, P.; Lye, P. G.; Koppenol, W. H. Chem. Res. Toxicol. 1997, 10, 1285-1292.
58. Veltwisch, D.; Janata, E.; Asmus, K.-D. J. Chem. Soc., Perkin Trans. 2 1980, 146-153.
59. Richeson, C. E.; Mulder, Bowry, P. V. W.; Ingold, K. U. J. Am. Chem. Soc. 1998, 120, 7211-7219.
60. 2OH, respectively. This reaction cannot be ruled out.
61. NIEHS Spin-Trap DataBase; National Institute of Environmental Health Services, NIH: Research Triangle Park, NC; http://mole.chm.bris.ac.uk/stdb/.
62. 3 indeed might have been formed in these experiments, because exploratory experiments in this laboratory showed that the ESR spectra of (independently generated) DMPO-OH as well as DMPO-alkyl radical adducts were rapidly destroyed on addition of peroxynitric acid, with concomitant buildup of the spectrum of 1.
63. Landolt-Bönzstein, New Series, Group II, Magnetic Properties of Free Radicals, Vol. II/17d2; Fischer, H., Ed.; Springer-Verlag: Berlin, 1989; pp 81-88.
64. 13C splitting agrees nicely with the splitting (4.24 G) predicted for 3a by density functional theory (DFT) calculations on the B3LP/6-31G(d,p) level (H.-G. Korth, unpublished results).
65. . to POBN by DMSO.
66. Sridhar, R.; Beaumont, P. C.; Powers, E. L. J. Radioanal. Nucl. Chem. 1986, 107, 227.