6-Hydroxyquinoline-N-oxides: A new class of "Super" photoacids

Journal of the American Chemical Society

Volumn 127, Issue 23, 2005, Pages 8534-8544

  Solntsev, Kyril M ^a   Glower, Caroline E ^a,c   Tolbert, Laren M ^a   Huppert, Dan ^b  

^a GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

^b TEL AVIV UNIVERSITY   (Israel)

^c Clayton College and State University ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDITY; BIOLOGY; NITROGEN; PHOTOCHEMICAL REACTIONS;

DEOXYGENATION; HYDROXYQUINOLINES; PHOTOBIOLOGY; STEADY STATE EMISSIONS;

ACIDS;

2 METHYL 6 HYDROXYQUINOLINE N OXIDE; 6 HYDROXYQUINOLINE N OXIDE; QUINOLINOL DERIVATIVE; UNCLASSIFIED DRUG;

ACIDITY; ARTICLE; CHEMICAL ANALYSIS; OXIDATION; OXYGENATION; PROTON TRANSPORT;

EID: 20444484457     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0514545     Document Type: Article

References (98)

1. This is part of our series "Photochemistry of "Super" Photoacids". For the previous paper see: Solntsev, K. M.; Sullivan, E. N.; Tolbert, L. M.; Ashkenazi, S.; Leiderman, P.; Huppert, D. J. Am. Chem. Soc, 2004. 128, 12701-12708.
2. Agmon, N.; Rettis, W.; Groth, C. J. Am. Chem. Soc. 2002, 124, 1089-1096.
3. Tolbert, L. M.; Solntsev, K. M. Acc. Chem. Res. 2002, 35, 19-27.
4. Formosinho, S. J.; Arnaut, L. G. J. Photochem. Photobiol. A 1993, 73, 21-48.
5. Kasha, M. J. Chem. Soc., Faraday Trans. 2 1986, 82, 2379-2392.
6. Ormson, S. M.; Brown, R. G. Prog. React. Kinet. 1994, 19, 45-91.
7. Ameer-Beg, S.; Ormson, S. M.; Brown. R. G.; Matousek, P.; Towrie, M.; Nibbering, E. T. J.; Foggi, P.; Neuwahl, F. V. R. J. Phys. Chem. A 2001, 105, 3709-3718.
8. Douhal, A.; Lahmani, F.; Zewail, A. Chem. Phys. 1996, 207, 477-498.
9. Hetherington, W. M., III; Micheels, R. H.; Eisenthal, K. B. Chem. Phys. Lett. 1979, 66, 230-233.
10. Takeuchi, S.; Tahara, T. J. Phys. Chem. A 1998, 102, 7740-7753.
11. Chou, P.; Yu, W.; Chen, Y.; Wei, C.; Martinez, S. S. J. Am. Chem. Soc. 1998, 120, 12927-12934.
12. Folmer, D. E.; Wisniewski, E. S.; Castleman, A. W. Chem. Phys. Lett. 2000, 318, 637-643.
13. Herbich, J.; Hung, C.; Thummel, R. P.; Waluk, J. J. Am. Chem. Soc. 1996, 118, 3508-3518.
14. Mente, S.; Maroncelli, M. J. Phys. Chem. A 1998, 102, 3860-3876.
15. Waluk, J. Acc. Chem. Res. 2003, 36, 832-838.
16. Itoh, M.; Adachi, T.; Tokumura, K. J. Am. Chem. Soc. 1984, 106, 850-855.
17. Konijnenberg, J.; Ekelmans, G. B.; Huizer, A. H.; Vanna, C. A. J. Chem. Soc., Faraday Trans. 2 1989, 55, 39-51.
18. (a) Lee, S. I.; Jang, D. J. J. Phys. Chem. 1995, 99, 7537-7541.
19. (b) Kim, T. G.; Lee, S. I.; Jang, D. J.; Kim, Y. J. Phys. Chem. 1995, 99, 12698-12700.
20. Bardez, E.; Boutin, P.; Valeur, B. Chem. Phys. Lett. 1992, 191, 142-148.
21. (a) Fang, W.-H. J. Phys. Chem. A 1999, 103, 5567-5573.
22. (b) Bardez, E. Isr. J. Chem. 1999, 39, 319-332.
23. (a) Kohtani, S.; Tagami, A.; Nakagaki, R. Chem. Phys. Lett. 2000, 316, 88-93.
24. (b) Matsumoto, Y.; Ebata, T.; Mikami, N. J. Phys. Chem. A 2002. 106, 5591-5599.
25. Bach, A.; Tanner, C.; Manca, C.; Frey, H.-M.; Leutwyler, S. J. Chem. Phys. 2003, 119, 5933-5942.
26. Chou, P.-T.; Wei, C.-Y.; Wang, C.-R. C.; Huns, F.-T.; Chang, C.-P. J. Phys. Chem. A 1999, 103, 1939-1949.
27. Kwon, O.-H.; Doo, H.; Lee, Y.-S.; Sans, D.-J. ChemPhysChem 2003, 4, 1079-1083.
28. (a) Bardez, E.; Chatelain, A.; Larrey. B.; Valeur, B.; J. Phys. Chem. 1994, 95, 2357-2366.
29. (b) Kim, T. G.; Kim, Y.; Jang. D.-J. J. Phys. Chem. A 2001, 105, 4328-4332.
30. (c) Poizat, O.; Bardez, E.; Buntinx, G.; Alain, V. J. Phys. Chem. A 2004. 108, 1873-1880.
31. Bardez, E.; Fedorov, A.; Berberan-Santos, M. N.; Martinho, J. M. G. J. Phys. Chem. A 1999, 103, 4131-4136.
32. Kim, T. G.; Topp, M. R. J. Phys. Chem. A 2004, 108, 10060-10065.
33. Jones, G.; Baty, D. J. In Quinolines. Part II; Jones, G., Ed.; Wiley: Chichester. 1982: Chapter 3.
34. Reviews: (a) Spence, G. G.; Taylor, E. C.; Buchardt, O. Chem. Rev. 1970, 70, 231-265.
35. (b) Bellamy, F.; Streith, J. Heterocycles 1976, 4. 1391-1447.
36. (C) Albini, A.; Alpegiani, M. Chem. Rev. 1984, 84, 43-71.
37. (d) Kurasawa, Y.; Takada, A.; Kim. H. S. J. Heierocycl. Chem. 1995, 32, 1085-1114.
38. (a) Kubota, T.; Miyazaki, H. Chem. Pharm. Bull. 1961, 9, 948-961.
39. (b) Andreev, V. P.; Ryzhakov, A. V. Chem. Heterocycl. Cmpd. 1993, 29, 1435-1440.
40. (a) Wardman, P.; Dennis, M. F.; Everett, S. A.; Patel, K. B.; Stratford, M. R. L.; Tracy, M. Biochem. Soc. Symp. 1995, 61, 171-194.
41. (b) Cerecetto, H.; Gonzalez, M. Mini-Rev. Med. Chem, 2001, 1, 219-231.
42. (a) Fuchs, T.; Gates, K. S.; Hwang, J.-T.; Greenberg. M. M. Chem. Res. Toxicol. 1999, 12, 1190-1194.
43. (b) Ban, F.; Gauld, J. W.; Boyd, R. J. J. Am. Chem. Soc. 2001, 123, 7320-7325.
44. (c) Inbaraj, J. J.; Motten, A. G.; Chignell, C. F. Chem. Res. Toxicol. 2003, 16, 164-170.
45. (d) Birincioglu, M.; Jaruga, P.; Chowdhury, G.; Rodriguez, H.; Dizdaroglu, M.; Gates, K. S. J. Am. Chem. Soc. 2003, 125, 11607-11615.
46. (e) Shi, X.; Platz.; M. S. J. Phys. Chem. A 2004, 108, 4385-4390
47. Cerecetto, H.; Dias, E.; Di Maio, R.; Gonzalez, M.; Pacce, S.; Saenz, P.; Seoane, G.; Suescun, L.; Mombru, A.; Fernandez, G.; Lema, M.; Villalba, J. J. Agric. Food Chem. 2000, 48, 2995-3002.
48. (a) Williams, L.; Chou, M. W.; Yan, J.; Young, J. F.; Chan, P. C.; Doerge, D. R. Toxicol. Appl. Pharm. 2002, 182, 98-104.
49. (b) Karlson-Stiber, C.; Persson, H. Toxicon 2003, 42, 339-349.
50. (a) Rothery, R. A.; Weiner, J. H. Eur. J. Biochem. 1998, 254, 588-595.
51. (b) Maklashina, E.; Cecchini, G. Arch. Biochem. Biophys. 1999, 369, 223-232.
52. (c) Nakayama, Y.; Hayashi, M.; Yoshikawa, K.; Mochida, K.; Unemoto, T. Biol. Pharm. Bull. 1999, 22, 1064-1067.
53. (d) Rothery, R. A.; Blasco, F.; Weiner, J. H. Biochemistry, 2001, 40, 5260-5268.
54. (e) Simkovic, M.; Frerman, F. E. Biochem. J. 2004, 378, 633-640.
55. Van Ark, G.; Berden, J. A. Biochim. Biophys. Acta 1977, 459, 119-137.
56. (a) Thomas, S. B.; Jones, T. Idwal, Griffiths, D. G. Dairy Ind. 1963, 25, 812-17.
57. (b) McMillian, M. K.; Li, L.; Parker, J. B.; Patel, L.; Zhong, Z.; Gunnett, J. W.; Powers, W. J.; Johnson, M. D. Cell Biol. Toxicol. 2002. 18, 157-173.
58. (c) Hamid, R.; Rotshteyn, Y.; Rabadi. L.; Parikh, R.; Bullock, P. Toxicol. in Vitro 2004, 18, 703-710.
59. (a) Reyes, R.; Martinez, J. C.; Delgado, N. M.; Merchant-Larios, H. Arch. Androl. 2002, 48, 209-219.
60. (b) Handbook of Fluorescent Probes and Research Products, 9th ed.; Haughland, R. P.; Ed.; Molecular Probes: Eugene, OR. 2003; Chapter 15.2.
61. (a) Favaro, G. Mol. Photochem. 1971, 2, 323-329.
62. (b) Aloisi, G. G.; Favaro, G. J. Chem. Soc., Perkin Trans. 2 1976, 4, 456-460.
63. Weller, A. Prog. React. Kinet. 1961, 1, 189-214.
64. Wans, T.-C; Chen, Y.-L.; Lee, K.-H.; Tzeng, C.-C. Synthesis 1997, 1, 87-90.
65. Hoegberg, S.; Elman, B.; Liem, H.; Madan, K.; Moberg, C.; Muhammed, M.; Sjoeberg, B.; Weber, M. World Patent WO8401947, 1984.
66. Wang, T.; Wallace, O. B.; Meanwell, N. A.; Kadow, J. F.; Zhang, Z.; Yang, Z. World Patent WO2003092695. 2003.
67. Gardecki, J. A.; Maroncelli, M. Appl. Spectrosc. 1998, 52, 1179-1189.
68. Genosar, L.; Cohen, B.; Huppert, D. J. Phys. Chem. A 2000, 104, 6689-6698.
69. Gauglitz, G.; Hubig, S. J. Photochem. 1981, 15, 255-257.
70. 2O.
71. Rosés, M.; Rived, F.; Bosch, E. J. Chromatogr., A 2000, 867, 45-56.
72. See Supporting Information for more data, details, and analysis.
73. (a) Bosch, E.; Bou, P.; Allemann, H.; Rosés, M. Anal. Chem. 1996, 68, 3651-3657.
74. (b) Avdeef, A.; Box, K. J.; Comer, J. E. A.; Gilses, M.; Hadley, M.; Hibbert, C.; Patterson, W.; Tam, K. Y. J. Pharm. Biomed. Anal. 1999, 20, 631-641.
75. (c) Canals, L; Portal, J. A.; Bosch, E.; Rosés, M. Anal. Chem. 2000, 72, 1802-1809.
76. (d) Canals, I.; Valko, K.; Bosch, E.; Hill, A. P.; Rosés. M. Anal. Chem. 2001, 73, 4937-4945.
77. (e) Canals, I.; Oumada, F. Z.; Rosés, M.; Bosch, E. J. Chromatogr., A 2001, 911, 191-202.
78. Mehata, M. S.; Joshi, H. C.; Tripath, H. B. Chem. Phys. Lett. 2002. 359, 314-320.
79. Janata, E. Proc. Indian Acad. Sci. Chem. Sci. 2002, 114, 731-737.
80. Al-Zagoum, M. N.; Warren, G. G. J. Inorg. Nucl. Chem. 1969, 31, 3465-3470.
81. Solntsev, K. M.; Huppert, D.; Agmon, N.; Tolbert, L. M. J. Phys. Chem. A 2000, 104, 4658-4669.
82. See for example Figure 10 in: Solntsev, K. M.; Al-Ainain, S. A.; Il'ichev, Y. V.; Kuzmin, M. G. J. Phys. Chem. A 2004, 108, 8212-8222.
83. Mansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165-195.
84. (a) Albini, A.; Fasani, E.; Frattini, V. J. Photochem. 1987, 37, 355-361.
85. (b) Bucher, G.; Scaiano, J. C. J. Phys. Chem. 1994, 98, 12471-12473.
86. Botchway, S. W.; Chakrabarti, S.; Makrigior, G. M. Photochem. Photobiol. 1998, 67, 635-640.
87. (a) Pines, E.; Huppert, D.; Agmon, N. J. Chem. Phys. 1988, 88, 5620-5630.
88. (b) Agmon, N.; Pines, E.; Huppert, D. J. Chem. Phys. 1988, 89, 5631-5638.
89. Rini, M.; Pines, D.; Magnes, B.-Z.; Pines, E.; Nibbering, E. T. J. J. Chem. Phys. 2004, 121, 9593-9610.
90. (a) Gopich, I. V.; Solntsev, K. M.; Agmon, N. J. Chem. Phys. 1999, 110, 2164-2174.
91. (b) Agmon, N. J. Chem. Phys. 1999, 110, 2175-2180.
92. (c) Solntsev, K. M.; Agmon, N. Chem. Phys. Lett. 2000, 320, 262-268.
93. Krissinel, E. B.; Agmon, N. J. Comput. Chem. 1996, 17, 1085-1098.
94. (a) Popov, A. V.; Agmon, N. Pol. J. Chem. 2003, 77, 1659-1668.
95. (b) Agmon, N.; Popov, A. V. J. Chem. Phys. 2003, 119, 6680-6690.
96. Gladkikh, V. S.; Burshtein, A. T.; Tavernier, H. L.; Payer, M. D. J. Phys. Chem. A 2002, 106, 6982-6990.
97. Popov, A. V.; Agmon, N. J. Chem. Phys. 2002, 117, 4376-4385.
98. Cohen, B.; Huppert, D. J. Phys. Chem. A 2001, 105, 2980-2988.