Photochemistry of N-hydroxy-2(1H)-pyridone, a more selective source of hydroxyl radicals than N-hydroxypyridine-2(1H)-thione

Journal of the American Chemical Society

Volumn 118, Issue 42, 1996, Pages 10124-10133

  Aveline, Béatrice M ^a   Kochevar, Irene E ^a   Redmond, Robert W ^a  

^a MASSACHUSETTS GENERAL HOSPITAL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PYRIDINE DERIVATIVE;

ARTICLE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PHOTOCHEMISTRY; SPECTROPHOTOMETRY;

EID: 0029905868     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961989l     Document Type: Article

References (76)

1. Halliwell, B.; Gutteridge, J. M. C. Free Radicals in Biology and Medicine; Oxford University Press: Oxford, 1989.
2. Bensasson, R. V.; Land, E. J.; Truscott, T. G. Excited States and Free Radicals in Biology and Medicine.; Oxford Science Publications: Oxford, 1993.
3. Hess, K. M.; Dix, T. A. Anal. Biochem. 1992, 206, 309-314.
4. Sako, M.; Nagai, K.; Maki, Y. J. Chem. Soc., Chem. Commun. 1993, 9, 750-751.
5. Adam, W.; Ballnier, D.; Epe, B.; Grimm, G. N.; Saha-Moller, C. R. Angew. Chem. Int. Ed. Engl. 1995, 34, 2156-2158.
6. Boivin, J.; Crepon, E.; Zard, S. Z. Tetrahedron Lett. 1990, 31, 6869-6872.
7. Barton, D. H. R.; Jaszberenyi, J. C.; Morrell, A. I. Tetrahedron Lett. 1991, 32, 311-314.
8. Reszka, K.; Chignell, C. F. Photochem. Photobiol. 1994, 60, 450-454.
9. Reszka, K.; Chignell, C. F. Photochem. Photobiol. 1995, 61, 269-275.
10. Aveline, B. M.; Kochevar, I. E.; Redmond, R. W. J. Am. Chem. Soc. 1996, 118, 289-290.
11. Aveline, B. M.; Kochevar, I. E.; Redmond, R. W. J. Am. Chem. Soc 1996, 118, 10113-10123.
12. Jones, R. A.; Katritzky, A. R. J. Chem. Soc. 1960, 2937-2942.
13. Aveline, B. M.; Kochevar, I. E.; Redmond, R. W. J. Am. Chem. Soc. 1995, 117, 9699-9708.
14. Taylor, E. C.; Kienzle, F.; McKillop, A. J. Org. Chem. 1970, 35, 1672-1674.
15. Taylor, E. C.; Altland, H. W.; Kienzle, F.; McKillop, A. J. Org. Chem. 1976, 41, 24-28.
16. The results of the investigation of the photochemistry of hydroxamic esters by laser flash photolysis will be published elsewhere.
17. •.
18. Gardner, J. N.; Katritzky, A. R. J. Chem. Soc. 1957, 4375-4387.
19. a of N-HP was spectrophotometrically verified to be 6.
20. Shaw, E.; Bernstein, J.; Losee, K.; Lott, W. A. J. Am. Chem. Soc. 1950, 72, 4362-4364.
21. Barton, D. H. R.; Bridon, D.; Fernandez-Picot, I.; Zard, S. Z. Tetrahedron 1987, 43, 2733-2740.
22. Krieg, M.; Srichai, M. B.; Redmond, R. W. Biochim. Biophys. Acta 1993, 1151, 168-174.
23. Aveline, B.; Hasan, T.; Redmond, R. W. Photochem. Photobiol. 1994, 59, 328-335.
24. Bensasson, R. V.; Land, E. J. Trans. Faraday Soc. 1971, 67, 1904-1915.
25. -1 25d at 530 nm) in deaerated benzene were used as standards.
26. (b) Gorman, A. A.; Hamblett, I.; Rodgers, M. A. J. J. Am. Chem. Soc. 1984, 106, 4679-4682.
27. (c) Inbar, S.; Linschitz, H.; Cohen, S. G. J. Am. Chem. Soc. 1981, 103, 1048-1054.
28. (d) Hurley, J. K.; Sinai, N.; Linschitz, H. Photochem. Photobiol. 1983, 38, 9-14.
29. Neta, P.; Schuler, R. H. J. Am. Chem. Soc. 1975, 97, 912-913.
30. Land, E. J.; Porter, G.; Strachan, E. Trans. Faraday Soc. 1961, 57, 1885-1893.
31. Nielsen, S. O.; Michael, B. D.; Hart, E. J. J. Phys. Chem. 1976, 80, 2482-2488.
32. Hatada, M.; Kraljiic, I.; El Sanahy, A.; Trumbore, C. N. J. Phys. Chem. 1974, 78, 888-891.
33. Kraljiic, I.; Trumbore, C. N. J. Am. Chem. Soc. 1965, 87, 2547-2550.
34. Dainton, F. S.; Wiseall, B. Trans. Faraday Soc. 1968, 64, 694-705.
35. Baxendale, J. H.; Khan, A. A. Int. J. Radiat. Phys. Chem. 1969, 1, 11-16.
36. Vidoczy, T.; Blinov, N. N.; Irinyi, G.; Gal, D. J. Chem. Soc., Faraday Trans. 1 1988, 84, 1075-1081.
37. -) in Aqueous Solution; National Bureau of Standards: Washington, DC, 1988; Vol. 17, p 523.
38. Irrespective of the environment (i.e. irrespective of the form considered), N-HP does not undergo intersystem crossing leading to triplet state formation. This was verified by a lack of triplet sensitization of merocyanine 540 in the case of aqueous and organic protic media and of β-carotene in the case of aprotic solvents.
39. To avoid interference with secondary kinetic processes.
40. Steenken, S.; O'Neill, P. J. Phys. Chem. 1979, 83, 2407-2411.
41. Jonsson, M.; Lind, J.; Reitberger, T.; Eriksen, T. E.; Merenyi, G. J. Phys. Chem. 1993, 97, 8229-8233.
42. Ascorbic acid 6-palmitate, methyl methacrylate, and benzhydrol were used at concentrations up to 0.2, 1, and 0.5 M, respectively.
43. Foti, M.; Ingold, K. U.; Lusztyk, J. J. Am. Chem. Soc. 1994, 116, 9440-9447.
44. See ref. 2, p 138.
45. These experiments were carried out in the presence of t-BuOH or DMSO to quench OH and prevent its reaction with α-tocopherol.
46. Mahoney, L. R.; Weiner, S. A. J. Am. Chem. Soc. 1972, 94, 1412-1413.
47. (a) Since the ester derivatives of N-HP are hydrolyzed in aqueous media, cold buffer was used as solvent to retard the degradation.
48. 2 (see eq 3) were studied in buffer at pH = 2 or pH = 10.
49. Ellison, D. H.; Salmon, G. A.; Wilkinson, F. Proc. R. Soc. London, Ser. A. 1972, 328, 23-36.
50. The band with a maximum at 480 nm observed in the presence of KSCN at pH = 2 is similar to that recorded under the same conditions but at neutral pH and displayed in Figure 7.
51. OH values under acidic conditions.
52. The similarity between the transient absorption spectra recorded for N-HP at pH = 7 and in protic organic solvents suggests that the photochemistry of the negatively-charged structure is either identical to that of the neutral form or different, but very inefficient.
53. 34
54. In both cases, the effect is to enhance the concentrations of radicals with the consequence that the radical-radical reaction process becomes more probable.
55. •- at 500 nm.
56. (b) Lambert, C.; Sarna, T.; Truscott, T. G. J. Chem. Soc., Faraday Trans. 1990, 86, 3879-3882.
57. See ref 34, p 518.
58. These experiments were carried out in the presence of t-BuOH in order to quench OH and avoid secondary reactions with the starting material.
59. 2 (see eq 3) were studied in buffer at pH = 7.
60. Icli, S. Tetrahedron 1990, 46, 2891-2902.
61. No detectable corresponding growth (with rise time ≤ 1 μs) in absorption was observed, preventing the identification of the product of reaction between OH and the starting pyridone.
62. - at 720 nm in water (see ref 34, p 515).
63. -1 in our study), suggesting that, although present in solution, the species formed by photoionization of N-HP could not be detected by our system,
64. (b) Danziger. R. M.; Hayon, E.; Langmuir, M. E. J. Phys. Chem. 1968, 72, 3842-3849.
65. This value was calculated using eq 7 after correction for the photoionization process undergone by N-HP.
66. Bordwell, F. G.; Singer, D. L.; Satish, A. V. J. Am. Chem. Soc. 1993, 115, 3543-3547.
67. 61b
68. (b) Bordwell, F. G.; Harrelson, J. A., Jr.; Lynch, T.-Y. J. Org. Chem. 1990, 55, 3337-3341.
69. Creed, D. Photochem. Photobiol. 1984, 39, 563-575.
70. Feitelson, J.; Hayon, E.; Treinin, A. J. Am. Chem. Soc. 1973, 95, 1025-1029.
71. Mialocq, J.-C.; Sutton, J.; Goujon, P. J. Chem. Phys. 1980, 72, 6338-6345.
72. Pileni, M. P.; Lavalette, D.; Muel, B. J. Am. Chem. Soc. 1975, 97, 2283-2284.
73. Dixon, W. T.; Murphy, D. J. Chem. Soc., Faraday Trans. 2 1976, 72, 1221-1230.
74. Dixon, W. T.; Murphy, P. J. Chem. Soc., Faraday Trans. 2 1978, 74, 432-439.
75. Holton, D. M.; Murphy, D. J. Chem. Soc., Faraday Trans. 2 1979, 75, 1637-1642.
76. Noyce, D. S.; Virgilio, J. A.; Bartman, B. J. Org. Chem. 1973, 38, 2657-2660.