Superoxide radical anion adduct of 5,5-dimethyl-1-pyrroline W-oxide (DMPO). 1. the thermodynamics of formation and its acidity

Journal of Physical Chemistry A

Volumn 109, Issue 27, 2005, Pages 6083-6088

  Villamena, Frederick A ^a   Merle, John K ^b   Hadad, Christopher M ^b   Zweier, Jay L ^a  

^a THE OHIO STATE UNIVERSITY COLLEGE OF MEDICINE   (United States)

^b OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOMEDICAL RESEARCH; CORRINS; POLARIZABLE CONTINUUM MODEL (PCM); SPIN TRAPPING;

ACIDITY; CONFORMATIONS; ELECTRON SPIN RESONANCE SPECTROSCOPY; FREE RADICALS; NEGATIVE IONS; OXYGEN; PROBABILITY DENSITY FUNCTION; SYNTHESIS (CHEMICAL); THERMODYNAMICS; WATER;

AROMATIC COMPOUNDS;

5,5 DIMETHYL 1 PYRROLINE 1 OXIDE; 5,5-DIMETHYL-1-PYRROLINE-1-OXIDE; AMINE OXIDE; ANION; HYDROXYL RADICAL; SUPEROXIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTRON; ELECTRON SPIN RESONANCE; KINETICS; OXIDATION REDUCTION REACTION; SPIN LABELING; SPIN TRAPPING; THERMODYNAMICS;

ANIONS; CYCLIC N-OXIDES; ELECTRON SPIN RESONANCE SPECTROSCOPY; ELECTRONS; HYDROXYL RADICAL; KINETICS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; SPIN LABELS; SPIN TRAPPING; SUPEROXIDES; THERMODYNAMICS;

EID: 22944474269     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp052431f     Document Type: Article

References (73)

1. Bonnett, R.; Brown, R. F. C.; Clark, V. M.; Sutherland, I. O.; Todd, A. J. Chem. Soc., Abstr. 1959, 2094-2102.
2. Iwamura, M.; Inamoto, N. Bull. Chem. Soc. Jpn. 1967, 40, 703.
3. Janzen, E. G.; Evans, C. A. J. Am. Chem. Soc. 1973, 95, 8205.
4. Harbour, J. R.; Chow, V.; Bolton, J. R. Can. J. Chem. 1974, 52, 3549-3553.
5. Adrian, F. J.; Cochran, E. L.; Bowers, V. A. J. Chem. Phys. 1967, 47, 5441-5442.
6. Meisel, D.; Levanon, H.; Czapski, G. J. Phys. Chem. 1974, 78, 779-782.
7. Saito, E.; Bielski, B. H. J. J. Am. Chem. Soc. 1961, 83, 4467-4468.
8. Yamakoshi, Y.; Sueyoshi, S.; Fukuhara, K.; Miyata, N.; Masumizu, T.; Kohno, M. J. Am. Chem. Soc. 1998, 120, 12363-12364.
9. Makino, K.; Mossoba, M. M.; Riesz, P. J. Am. Chem. Soc. 1982, 104, 3537-3539.
10. Stoyanovsky, D. A.; Clancy, R.; Cederbaum, A. I. J. Am. Chem. Soc. 1999, 121, 5093-5094.
11. Jones, C. M.; Burkitt, M. J. J. Am. Chem. Soc. 2003, 125, 6946-6954.
12. Pryor, W. A.; Terauchi, K.; Davis, W. H. J. Environ. Health Perspect. 1976, 16, 161-176.
13. Pou, S.; Pou, W. S.; Bredt, D. S.; Snyder, S. H.; Rosen, G. M. J. Biol. Chem. 1992, 267, 24173-24176.
14. Harbour, J. R.; Bolton, J. R. Biochem. Biophys. Res. Commun. 1975, 64, 803-807.
15. Xia, Y.; Zweier, J. L. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 6954-6958.
16. Rosen, G. M.; Britigan, B. E.; Cohen, M. S.; Ellington, S. P.; Barber, M. J. Biochim. Biophys. Acta 1988, 969, 236-241.
17. Chamulitrat, W.; Hughes, M. F.; Eling, T. E.; Mason, R. P. Arch. Biochem. Biophys. 1991, 290, 153-159.
18. Zweier, J. L. J. Biol. Chem. 1988, 263, 1353-1357.
19. Zweier, J. L.; Kuppusamy, P.; Lutty, G. A. Proc. Natl. Acad. Sci. 1988, 85, 4046-4050.
20. Buettner, G. R.; Oberley, L. W. Biochem. Biophys. Res. Commun. 1978, 83, 69-74.
21. Finkelstein, E.; Rosen, G. M.; Rauckman, E. J. Mol. Pharm. 1982, 21, 262-265.
22. Pou, S.; Hassett, D. J.; Britigan, B. E.; Cohen, M. S.; Rosen, G. M. Anal. Biochem. 1989, 177, 1-6.
23. Frejaville, C.; Karoui, H.; Tuccio, B.; Le Moigne, F.; Culcasi, M.; Pietri, S.; Lauricella, R.; Tordo, P. J. Med. Chem. 1995, 38, 258-265.
24. Liu, K. J.; Miyake, M.; Panz, T.; Swartz, H. Free Radical Biol. Med. 1999, 26, 714-721.
25. Stolze, K.; Udilova, N.; Nohl, H. Free Radical Biol. Med. 2000, 29, 1005-1014.
26. Chalier, F.; Tordo, P. J. Chem. Soc., Perkin Trans. 2 2002, 2110-2117.
27. Olive, G.; Mercier, A.; Le Moigne, F.; Rockenbauer, A.; Tordo, P. Free Radical Biol. Med. 2000, 28, 403-408.
28. Zhang, H.; Joseph, J.; Vasquez-Vivar, J.; Karoui, H.; Nsanzumuhire, C.; Martasek, P.; Tordo, P.; Kalyanaraman, B. FEBS Lett 2000, 473, 58-62.
29. Stolze, K.; Udilova, N.; Nohl, H. Biol. Chem. 2002, 383, 813-820.
30. Stolze, K.; Udilova, N.; Rosenau, T.; Hofmger, A.; Nohl, H. Biol. Chem. 2003, 384, 493-500.
31. Tsai, P.; Ichikawa, K.; Mailer, C.; Pou, S.; Halpern, H. J.; Robinson, B. H.; Nielsen, R.; Rosen, G. M. J. Org. Chem. 2003, 68, 7811-7817.
32. Zhao, H.; Joseph, J.; Zhang, H.; Karoui, H.; Kalyanaraman, B. Free Radical Biol. Med. 2001, 31, 599-606.
33. Villamena, F.; Zweier, J. J. Chem. Soc., Perkin Trans. 2 2002, 1340-1344.
34. Villamena, F. A.; Merle, J. K.; Hadad, C. M.; Zweier, J. L. J. Phys. Chem. A 2005, 109, 6089-6098.
35. Labanowski, J. W.; Andzelm, J. Density Functional Methods in Chemistry; Springer: New York, 1991.
36. Parr, R. G.; Yang, W. Density Functional Theory in Atoms and Molecules; Oxford University Press: New York, 1989.
37. Hehre, W. J.; Radom, L.; Schleyer, P. V.; Pople, J. A. Ab Initio Molecular orbital Theory; John Wiley & Sons: New York, 1986.
38. Becke, A. D. Phys. Rev. A 1988, 38, 3098.
39. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
40. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
41. Tomasi, J.; Persico, M. Chem. Rev. 1994, 94, 2027.
42. Cossi, M.; Barone, V.; Cammi, R.; Tomasi, J. Chem. Phys. Lett. 1996, 255, 327.
43. Barone, V.; Cossi, M.; Tomasi, J. J. Chem. Phys. 1997, 107, 3210.
44. Barone, V.; Cossi, M.; Tomasi, J. J. Comput. Chem. 1998, 19, 404.
45. Cossi, M.; Barone, V. J. Chem. Phys. 1998, 109, 6246.
46. Frisch, M. J.; et al. Gaussian 98, revision A.11.3; Gaussian, Inc.: Pittsburgh, PA, 2002.
47. Frisch, M. J.; et al. Gaussian 03, revision B.04; Gaussian, Inc.: Pittsburgh, PA, 2003.
48. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502-16513.
49. Ochterski, J. W.; Petersson, G. A.; Montgomery, J. A., Jr. J. Chem. Phys. 1996, 104, 2598.
50. Montgomery, J. A., Jr.; Frisch, M. J.; Ochterski, J. W.; Petersson, G. A. J. Chem. Phys. 1999, 110, 2822.
51. Montgomery, J. A., Jr.; Frisch, M. J.; Ochterski, J. W.; Petersson, G. A. J. Chem. Phys. 2000, 112, 6532.
52. Woon, D. E.; Dunning, T. H. J. Chem. Phys. 1995, 103, 4572.
53. Xu, Y. K.; Chen, Z. W.; Sun, J.; Liu, K.; Chen, W.; Shi, W.; Wang, H. M.; Zhang, X. K.; Liu, Y. J. Org. Chem. 2002, 67, 7624-7630.
54. Villamena, F. A.; Dickman, M. H.; Crist, D. R. Inorg. Chem. 1998, 37, 1446-1453.
55. Boeyens, J. C. A.; Kruger, G. J. Acta Crystallogr. 1970, B26, 668.
56. Alini, S.; Citterio, A.; Farina, A.; Fochi, M. C.; Malpezzi, L. Acta Crystallogr. 1998, C54, 1000-1003.
57. Mahoney, L. R.; Mendenhall, G. D.; Ingold, K. U. J. Am. Chem. Soc. 1973, 95, 8610-8614.
58. Bartberger, M. D.; Fukuto, J. M.; Houk, K. N. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 2194-2198.
59. Mujika, J. I.; Mercero, J. M.; Lopez, X. J. Phys. Chem. A 2003, 107, 6099-6107.
60. Silva, C. O.; da Silva, E. C.; Nascimento, M. A. C. J. Phys. Chem. A 2000, 104, 2402-2409.
61. Pliego, J. R.; Riveros, J. M. J. Phys. Chem. A 2002, 106, 7434-7439.
62. To reproduce the solvent parameters of Tomasi et al. that existed in the Gaussian 94 implementation using Gaussian 98, a routine using "scrf=oldpcm" was used.
63. Wiberg, K. B.; Laidig, K. E. J. Am. Chem. Soc. 1988, 110, 1872-1874.
64. Wang, X.; Houk, K. N. J. Am. Chem. Soc. 1988, 110, 1870-1872.
65. Saracino, G. A. A.; Tedeschi, A.; D'Errico, G.; Improta, R.; Franco, L.; Ruzzi, M.; Corvaia, C.; Barone, V. J. Phys. Chem. A 2002, 106, 10700-10706.
66. Richardson, W. H.; Hodge, V. F. J. Org. Chem. 1970, 35, 4012-4016.
67. Behar, D.; Czapski, G.; Rabani, J.; Dorfman, L. M.; Schwarz, H. A. J. Phys. Chem. 1970, 74, 3209-3213.
68. Jonsson, M. J. Phys. Chem. 1996, 100, 6814-6818.
69. Serjeant, E. P.; Dempsey, B. Ionisation Constants of Organic Liquids in Aqueous Solution; Pergamon: New York, 1979.
70. Czapski, G.; Bielski, B. H. J. J. Phys. Chem. 1963, 67, 2180-2184.
71. Buettner, G. R. Arch. Biochem. Biophys. 1993, 300, 535-543.
72. Finkelstein, E.; Rosen, G. M.; Rauckman, E. J. J. Am. Chem. Soc. 1980, 102, 4995.
73. Villamena, F.; Hadad, C. M.; Zweier, J. J. Phys. Chem. A 2003, 107, 4407-4414.