Experimental and theoretical studies of the proton-hopping reaction of 7-hydroxyquinoline in viscous hydroxylic media

Journal of Physical Chemistry A

Volumn 102, Issue 45, 1998, Pages 8871-8880

  Garcia Ochoa I ^a   Bisht, P B ^b   Sanchez F ^c   Martinez Ataz E ^a   Santos, L ^a   Tripathi, H B ^d   Douhal, A ^a  

^a UNIVERSITY OF CASTILLA LA MANCHA   (Spain)

^b INDIAN INSTITUTE OF TECHNOLOGY MADRAS   (India)

^c INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^d KUMAUN UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000447011     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp981489+     Document Type: Article

References (71)

1. (a) Stryer, L. Biochemistry, 4th ed.; W. H. Freeman: New York, 1995.
2. (b) Schowen, R. L. Angew Chem., Int. Ed. Engl. 1997, 36, 1434 and references therein.
3. (a) Gerner, B. J.; Hynes, J. T. Science 1996, 271, 1563.
4. (b) Ando, K.; Hynes, J. T. J. Phys. Chem. B 1997, 101, 10464.
5. (c) Bianco, R.; Hynes, J. T. J. Phys. Chem. A 1998, 102, 309.
6. (a) Nagle, J. F.; Morowitz, H. J. Proc. Natl. Acad. Sci. U.S.A. 1978, 75, 298.
7. (b) Pomès, R.; Roux, B. J. Phys. Chem. 1996, 100, 2519.
8. (c) Ber. Bunsen-Ges. Phys. Chem. 1998, 3.
9. Borgis, D. In Electron and Proton Transfer in Chemistry and Biology; Müller, A., Ratajczak, H., Junge. W., Deign, E., Eds.; Elsevier: Amsterdam, 1992.
10. (a) Taylor, C. A.; El-Bayoumi, M. A.; Kasha, M. Proc. Natl. Acad. Sci. U.S.A. 1969, 63, 253.
11. (b) Ingham, K. C.; El-Bayoumi, M. A. J. Am. Chem. Soc. 1974, 96, 1674.
12. (c) Tokumura, K.; Wanatabe, Y.; Udagawa, M.; Itoh, M. J. Am. Chem. Soc. 1987, 109, 1346.
13. (d) Fuke, K.; Kaya, K. J. Phys. Chem. 1989, 93, 614.
14. (e) Kim, S. K.; Bernstein, E. R. J. Phys. Chem. 1990, 94, 3531.
15. (f) Chapman, F. C.; Maroncelli, M. J. Phys Chem. 1992, 96, 8430.
16. (g) Huang, Y.; Arnold, S.; Sulkes, M. J. Phys. Chem. 1996, 100, 4734.
17. (h) Smirnov, A. V.; English, D. S.; Rich, R. L.; Lane, J.; Teyton, L.; Schwabacher, A. W.; Luo, S.; Thornburg, R. W.; Petrich, J. W. J. Phys. Chem. B 1997, 101, 2758.
18. (i) Mente, S.; Marroncelli, M. J. Phys. Chem. A 1998, 102, 3860.
19. Douhal, A.; Lahmani, F.; Zewail, A. H. Chem. Phys. 1996, 207.
20. (a) Douhal, A.; Kim, S. K.; Zewail, A. H. Nature 1995, 378, 260.
21. (b) Douhal, A.; Guallar, V.; Moreno, M.; Lluch, J. M. Chem. Phys. Lett. 1996, 256, 370.
22. (c) Chachivilis, M.; Fiebig, T.; Douhal, A.; Zewail, A. H. J. Phys. Chem. A 1998, 102, 669.
23. (a) Schulman, S.; Fernando, Q. Tetrahedron 1968, 24, 1777.
24. (b) Mason, S. F.; Philp, J.; Smith, B. E. J. Chem. Soc. A 1968, 3051.
25. (c) Thistlethwaite, P. J.; Corkill, P. J. Chem. Phys. Lett. 1982, 85, 317.
26. (d) Terazima, M.; Azumi, T. J. Am. Chem. Soc. 1989, 111, 3824.
27. (e) Lavin, A.; Collins, S. Chem. Phys. Lett. 1993, 204, 96. Lavin, A.; Collins, S. Chem. Phys. Lett. 1993 207, 513.
28. (e) Lavin, A.; Collins, S. Chem. Phys. Lett. 1993, 204, 96. Lavin, A.; Collins, S. Chem. Phys. Lett. 1993 207, 513.
29. (f) Lavin, A.; Collins, S. J. Phys. Chem. 1993, 97, 13615.
30. (g) Bohra, A.; Lavin, A.; Collins, S. J. Phys. Chem. 1994, 98, 11424.
31. (h) Bardez, E.; Devol, I.; Larrey, B.; Valeur, B. J. Phys. Chem. B 1997, 101, 7786.
32. (i) Naik, D. B.; Dwibedy, P.; Dey, G. R.; Kishore, K.; Moorthy, P. N. J. Phys. Chem. A 1998, 102, 684.
33. (j) Wei, C.-Y.; Yu, W.-S.; Chou, P.-T.; Hung, F.-T.; Chang, C.-P.; Lin, T.-C. J. Phys. Chem. B 1998, 102, 1053.
34. (a) Itoh, M.; Adachi, T.; Tokumura, K. J. Am. Chem. Soc. 1983, 105, 4828.
35. (b) Itoh, M.; Adachi, T.; Tokumura, K. J. Am. Chem. Soc. 1984, 106, 850.
36. (c) Tokumura, K.; Itoh, M. J. Phys. Chem. 1984, 88, 3921.
37. (d) Nagakawa, T.; Kohtani, S.; Itoh, M. J. Am. Chem. Soc. 1995, 117, 7952.
38. (e) Tokumura, K.; Natsume, M.; Nakagawa, T.; Hashimoto, M.; Yuzawa, T.; Hamahuchi, H.; Itoh, M. Chem. Phys. Lett. 1997, 271, 320.
39. Konijnenberg, J.; Ekelmans, G. B.; Huizer, A. H.; Varma, C. A. G. O. J. Chem. Soc., Faraday Trans. 2 1989, 85, 39.
40. (a) Lee, S. I.; Jang, D. J. J. Phys. Chem. 1995, 99, 7537.
41. (b) Kim, T.-K.; Lee, S.-I.; Jang, D.-J.; Kim, Y. J. Phys. Chem. 1995, 99, 12698.
42. Lahmani, F.; Douhal, A.; Breheret, E.; Zehnacker-Rentien, A. Chem. Phys. Lett. 1994, 220, 235.
43. Douhal, A.; Sastre, R. Chem. Phys. Lett. 1994, 219, 91.
44. Douhal, A.; Dabrio, J.; Sastre, R. J. Phys. Chem. 1996, 100, 149.
45. Bardez, E.; Chatelain, A.; Larrey, B.; Valeur, B. J. Phys. Chem. 1994, 98, 2357.
46. (a) Oikawa, A.; Abe, H.; Mikami, N.; Ito, M. J. Phys. Chem. 1984, 88, 5180.
47. (b) Hollas, J. M.; Bin Hussein, M. Z. J. Mol. Spectrosc. 1988, 127, 127.
48. (c) Johnson, J. R.; Jordan, K. D.; Plusquellic, D. F.; Pratt. D. W. J. Chem. Phys. 1990, 93, 2258.
49. Stewart, J. J. P. Comput. Chem. 1995, 10, 209.
50. We acknowledge Cambridge Software for allowing the use of a betaversion of Chem3D 3.5.
51. MM+ in Hyperchem, version 4.5; Autodesck Inc.: Sausalito, CA, 1995.
52. Anders, E.; Koch, R.; Freunscht, P. J. Comput. Chem. 1973, 14, 1301.
53. Benesi, H. A.; Hildebrand, J. H. J. Am. Chem. Soc. 1949, 71, 2703.
54. Reynolds, L.; Gardecki, J. A.; Franckland, J. V.; Horng, M. L.; Maroncelli, M. J. Phys. Chem. 1996, 100, 10337.
55. Douhal, A. J. Phys. Chem. 1994, 98, 13131.
56. Ware, W. R.; Brand, L. J. Phys. Chem. 1979, 83, 795.
57. Kim, S. K.; Breen, J. J.; Willberg, D. M.; Peng, L. W.; Heikal, A.; Syage, J. A.; Zewail, A. H. J. Phys. Chem. 1995, 99, 7421.
58. (a) Fields, M. J.; Hiller, I. H.; Guest, M. F. J. Chem. Soc., Chem. Commun. 1984, 1310.
59. (b) Lledos, A.; Bertran, J. J. Mol. Struct. (THEOCHEM) 1985, 73, 120.
60. (c) Sobolewski, A. L.; Adamowicz, L. J. Phys. Chem. 1995, 99, 14277.
61. Nimlos, M. R.; Kelley, D. F.; Bernstein, E. R. J. Phys. Chem. 1989, 93, 344.
62. Chou, P. T.; Wei, C. Y. J. Phys. Chem. 1997, 101, 9119.
63. The energy of stabilization due to the HBB is the energy difference between that of the bridged and that of separated (by 10 Å) species in 1:1 complexes.
64. Guallar, J.; Moreno, M.; Amat-Guerri, F.; Lluch, J. M.; Douhal, A. J. Phys. Chem. 1996, 100, 19789.
65. (a) Paz, J. J.; Moreno, M.; Lluch, J. M. J. Chem. Phys. 1995, 103, 353.
66. (b) Rovira, M. C.; Scheiner, S. J. Phys. Chem. 1995, 99, 9854.
67. (c) Colominas, C.; Luque, F. J.; Orozco, M. J. Am. Chem. Soc. 1996, 118, 6811.
68. Guthrie, J. P. J. Am. Chem. Soc. 1996, 118, 12886.
69. Scheiner, S.; Kar, T.; Cuma, M. J. Phys. Chem. A 1997, 5901.
70. Douhal, A. Science 1997, 276, 221.
71. See, for example: Zewail, A. H. J. Phys. Chem. 1996, 97, 9046 and references therein.