Remarkable accelerating effects of ammonium cations on electron-transfer reactions of quinones by hydrogen bonding with semiquinone radical anions

Journal of Physical Chemistry A

Volumn 108, Issue 47, 2004, Pages 10405-10413

  Okamoto, Ken ^a   Ohkubo, Kei ^a   Kadish, Karl M ^b   Fukuzumi, Shunichi ^a  

^a OSAKA UNIVERSITY   (Japan)

^b University of Houston   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACCELERATING EFFECTS; AMMONIUM CATIONS; ELECTRON TRANSFER REACTIONS; QUINONES;

AMMONIUM COMPOUNDS; CATALYSIS; CYCLIC VOLTAMMETRY; FLUORESCENCE; FREE ENERGY; HYDROGEN BONDS; PARAMAGNETIC RESONANCE; PERMITTIVITY; RATE CONSTANTS; REACTION KINETICS; REDOX REACTIONS;

POSITIVE IONS;

EID: 10044234151     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp046078+     Document Type: Article

References (95)

1. Kaim, W.; Schwederski, B. Bioinorganic Chemistry: Inorganic Elements in the Chemistry of Life; Wiley: Chichester, U.K., 1994.
2. Principles of Bioinorganic Chemistry; Lippard, S. J., Berg, J. M., Eds.; University Science Books: Mill Valley, CA, 1994.
3. Fukuzumi, S.; Ohtsu, H.; Ohkubo, K.; Itoh, S.; Imahori, H. Coord. Chem. Rev. 2002, 226, 71.
4. (a) Limburg, J.; Szalai, V. A.; Brudvig, G. W. J. Chem. Soc., Dalton Trans. 1999, 1353.
5. (b) Einsle, O.; Messerschmidt, A.; Stach, P.; Bourenkov, G. P.; Bartunik, H. D.; Huber, R.; Kroneck, P. M. H. Nature 1999, 400, 476.
6. (a) Riistama, S.; Laakkonen, L.; Wikström, M.; Verkhovsky, M. I.; Puustinen, A. Biochemistry 1999, 38, 10670.
7. (b) Xia, Z.-x.; Dai, W.-w.; Zhang, Y.-f.; White, S. A.; Boyd, G. D.; Mathews, F. S. J. Mol. Biol. 1996, 259, 480.
8. Ghosh, M.; Anthony. C.; Harlos, K.; Goodwin, M. G.; Blake, C. Structure 1995, 3. 177.
9. (a) Itoh, S.; Kawakami, H.; Fukuzumi, S. J. Am. Chem. Soc. 1997, 119, 439.
10. (b) Itoh, S.; Kawakami, H.; Fukuzumi, S. Biochemistry 1998, 37, 6562.
11. (c) Itoh, S.; Taniguchi, M.; Takada, N.; Nagatomo, S.; Kitagawa, T.; Fukuzumi, S. J. Am. Chem. Soc. 2000, 122, 12087.
12. (d) Itoh, S.; Kumei, H.; Nagatomo, S.; Kitagawa, T.; Fukuzumi, S. J. Am. Chem. Soc. 2001, 123, 2165.
13. (a) Fukuzumi, S.; Itoh, S. Antioxid. Redox. Signaling 2001, 3, 807.
14. (b) Itoh, S.; Taki, M.; Fukuzumi, S. Coord. Chem. Rev. 2000, 198, 3.
15. (a) Bruhn, H.; Nigam, S.; Holzwarth, J. F. Faraday Discuss. Chem. Soc. 1982, 74, 129.
16. (b) Santamaria, J. In Photoinduced Electron Transfer, Fox, M. A., Chanon, M., Eds.; Elsevier: Amsterdam, 1988; Part B, pp 483-540.
17. (c) Galan, M.; Dominguez, M.; Andreu, R.; Moya, M. L.; Sanchez, F.; Burgess, J. J. Chem. Soc., Faraday Trans. 1990, 86, 937.
18. (a) Sivaguru, J.; Natarajan, A.; Kaanumalle, L. S.; Shailaja, J.; Uppili, S.; Joy, A.; Ramamurthy, V. Acc. Chem. Res. 2003, 36, 509.
19. (b) Ramamurthy, V.; Robbins, R. J.; Thomas, K. J.; Lakshminarasimhan, P. H. In Molecular Solid State; Whitsell, J. K., Ed.; John Wiley & Sons Ltd.: Chichester, U.K., 1999; pp 63-140.
20. (a) Fukuzumi, S. In Advances in Electron-Transfer Chemistry; Mariano, P. S., Ed.; JAI Press: Greenwich, CT, 1992; Vol. 2, pp 67-175.
21. (b) Fukuzumi, S. Bull. Chem. Soc. Jpn. 1997, 70, 1.
22. (c) Fukuzumi, S.; Itoh, S. In Advances in Photochemistry; Neckers, D. C., Volman, D. H., von Bünau, G., Eds.; Wiley: New York, 1999; Vol. 25, pp 107-172.
23. (a) Fukuzumi, S. In Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 4, pp 3-67.
24. (b) Fukuzumi, S. Org. Biomol. Chem. 2003, 1, 609.
25. (c) Fukuzumi, S.; Imahori, H. In Photochemistry of Organic Molecules in Isotropic and Anisotropic Media; Ramamurthy, V., Schanze, K. S., Eds.; Marcel Delkker: New York, 2003; pp 227-273.
26. (a) Goodson, B.; Schuster, G. B. Tetrahedron Lett. 1986, 27, 3123.
27. (b) Schmehl, R. H.; Whitesell, L. G.; Whitten, D. G. J. Am. Chem. Soc. 1981, 103, 3761.
28. (c) Mizuno, K.; Ichinose, N.; Otsuji, Y. Chem. Lett. 1985, 455.
29. (d) Fukuzumi, S.; Kuroda, S.; Tanaka, T. J. Am. Chem. Soc. 1985, 107, 3020.
30. (e) Fukuzumi, S.; Koumitsu, S.; Hironaka, K.; Tanaka, T. J. Am. Chem. Soc. 1987, 109, 305.
31. (a) Fukuzumi, S.; Okamoto, T.; Otera, J. J. Am. Chem. Soc. 1994, 116, 5503.
32. (b) Fukuzumi, S.; Ohkubo, K.; Okamoto, T. J. Am. Chem. Soc. 2002, 124, 14147.
33. (c) Fukuzumi, S.; Satoh, N.; Okamoto. T.; Yasui, K.; Suenobu, T.; Seko, Y.; Fujitsuka, M.; Ito, O. J. Am. Chem. Soc. 2001, 123, 7756.
34. (a) Fukuzumi, S.; Ohkubo, K. Chem. Eur. J. 2000, 6, 4532.
35. (b) Fukuzumi, S.; Mori, H.; Imahori, H.; Suenobu, T.; Araki, Y.; Ito, O.; Kadish, K. M. J. Am. Chem. Soc. 2001, 123, 12458.
36. (c) Fukuzumi, S.; Fujii, Y.; Suenobu, T. J. Am. Chem. Soc. 2001, 123, 10191.
37. (a) Fukuzumi, S.; Inada, O.; Satoh, N.; Suenobu, T.; Imahori, H. J. Am. Chem. Soc. 2002, 124, 9181.
38. (b) Fukuzumi, S.; Yuasa, J.; Suenobu, T. J. Am. Chem. Soc. 2002, 124, 12566.
39. (a) Fukuzumi, S.; Okamoto, K.; Imahori, H. Angew. Chem., Int. Ed. 2002, 41, 620.
40. (b) Okamoto, K.; Imahori, H.; Fukuzumi, S. J. Am. Chem. Soc. 2003, 125, 7014.
41. (c) Fukuzumi, S.; Okamoto, K.; Yoshida, Y.; Imahori, H.; Araki, Y.; Ito, O. J Am. Chem. Soc. 2003, 125, 1007.
42. (a) Okamoto, K.; Araki, Y.; Ito, O.; Fukuzumi, S. J. Am. Chem. Soc. 2004, 126, 56.
43. (b) Okamoto, K.; Mori, Y.; Yamada, H.; Imahori, H.; Fukuzumi, S. Chem. Eur. J. 2004, 10, 474.
44. (a) Sivaguru, J.; Shailaja, J.; Ramamurthy, V. In Handbook of Zeolite Science and Technology; Auerbach, S. M., Carrado, K. A., Dutta, P. K., Eds.; Marcel Dekker: New York, 2003; pp 591-720.
45. (b) Laksh minarasimhan, P.; Thomas, K. J.; Johnston, L. J.; Ramamurthy, V. Langmuir 2000, 16, 9360.
46. Kuusk V.; McIntire, W. S. J. Biol. Chem. 1994, 269, 26136.
47. (a) Gorren A. C. F.; Duine, J. A. Biochemistry 1994, 33, 12202.
48. (b) Gorren, A. C. F.; de Vries, S.; Duine, J. A. Biochemistry 1995, 34, 9748.
49. (c) Gorren, A. C. F.; Moenne-Loccoz, P.; Backes, G.; de Vries, S.; Sanders-Loehr, J.; Duine, J. A. Biochemistry 1995, 34, 12926.
50. Moenne-Loccoz, P.; Nakamura, N.; Itoh, S.; Fukuzumi, S.; Gorren, A. C. F.; Duine, J. A.; Sanders-Loehr, J. Biochemistry 1996, 35, 4713.
51. (a) Bishop G. R.; Davidson, V. L. Biochemistry 1997, 36, 13586.
52. (b) Zhu, Z.; Davidson, V. L. Biochem. J. 1998, 329, 175.
53. (c) Sun, D.; Davidson, V. L. Biochemistry 2001, 40, 12285.
54. Stowell, M. H. B.; McPhillips, T.; Rees, D. C.; Soltis, S. M.; Abresch, E.; Feher, G. Science 1997, 276, 812.
55. (a) Rohrer, M.; MacMillan, F.; Prisner, T. F.; Gardiner, A. T.; Möbius, K.; Lubitz, W. J. Phys. Chem. B 1998, 102, 4648.
56. (b) Donato, M. D.; Peluso, A.; Villani, G. J. Phys. Chem. B 2004, 108, 3068.
57. (a) Graige, M. S.; Feher, G.; Okamura, M. Y. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 11679.
58. (b) Rabenstein, B.; Ullmann, G. M.; Knapp, E.-W. Biochemistry 2000, 39, 10487.
59. (c) Ermler, U.; Fritzsch, G.; Buchanan, S. K.; Michel, H. Structure 1994, 2, 925.
60. Ishikita, H.; Morra, G.; Knapp, E.-W. Biochemistry 2003, 42, 3882.
61. (a) Hutter, M. C.; Hughes, J. M.; Reimers, J. R.; Hush, N. S. J. Phys. Chem. B 1999, 103, 4906.
62. (b) Harvey, S. C. Proteins 1989, 5, 78.
63. For the salt effects on the radical ion pair produced in photoinduced electron transfer, see: (a) Thompson, P. A.; Simon, J. D. J. Am. Chem. Soc. 1993, 115, 5657.
64. For the salt effects on the radical ion pair produced in photoinduced electron transfer, see: (a) Thompson, P. A.; Simon, J. D. J. Am. Chem. Soc. 1993, 115, 5657. (b) Bockman, T. M.; Hubig, S. M.; Kochi, J. K. J. Am. Chem. Soc. 1998, 120, 2826. (c) Yabe, T.; Kochi, J. K. J. Am. Chem. Soc. 1992, 114, 4491. (d) Bockman, T. M.; Kochi, J. K. New J. Chem. 1992, 16, 39. (e) Grosso, V. N.; Previtali, C. M.; Chesta, C. A. Photochem. Photobiol. 1998, 68, 481. (f) Marcus, R. A. J. Phys. Chem. B 1998, 102, 10071. (g) Kluge, T.; Knoll, H. Photochem. Photobiol. A 2000, 130, 95. (h) Vakarin, E. V.; Holovko, M. F.; Piotrowiak, P. Chem. Phys. Lett. 2002, 363, 7.
65. For the salt effects on the radical ion pair produced in photoinduced electron transfer, see: (a) Thompson, P. A.; Simon, J. D. J. Am. Chem. Soc. 1993, 115, 5657. (b) Bockman, T. M.; Hubig, S. M.; Kochi, J. K. J. Am. Chem. Soc. 1998, 120, 2826. (c) Yabe, T.; Kochi, J. K. J. Am. Chem. Soc. 1992, 114, 4491. (d) Bockman, T. M.; Kochi, J. K. New J. Chem. 1992, 16, 39. (e) Grosso, V. N.; Previtali, C. M.; Chesta, C. A. Photochem. Photobiol. 1998, 68, 481. (f) Marcus, R. A. J. Phys. Chem. B 1998, 102, 10071. (g) Kluge, T.; Knoll, H. Photochem. Photobiol. A 2000, 130, 95. (h) Vakarin, E. V.; Holovko, M. F.; Piotrowiak, P. Chem. Phys. Lett. 2002, 363, 7.
66. For the salt effects on the radical ion pair produced in photoinduced electron transfer, see: (a) Thompson, P. A.; Simon, J. D. J. Am. Chem. Soc. 1993, 115, 5657. (b) Bockman, T. M.; Hubig, S. M.; Kochi, J. K. J. Am. Chem. Soc. 1998, 120, 2826. (c) Yabe, T.; Kochi, J. K. J. Am. Chem. Soc. 1992, 114, 4491. (d) Bockman, T. M.; Kochi, J. K. New J. Chem. 1992, 16, 39. (e) Grosso, V. N.; Previtali, C. M.; Chesta, C. A. Photochem. Photobiol. 1998, 68, 481. (f) Marcus, R. A. J. Phys. Chem. B 1998, 102, 10071. (g) Kluge, T.; Knoll, H. Photochem. Photobiol. A 2000, 130, 95. (h) Vakarin, E. V.; Holovko, M. F.; Piotrowiak, P. Chem. Phys. Lett. 2002, 363, 7.
67. For the salt effects on the radical ion pair produced in photoinduced electron transfer, see: (a) Thompson, P. A.; Simon, J. D. J. Am. Chem. Soc. 1993, 115, 5657. (b) Bockman, T. M.; Hubig, S. M.; Kochi, J. K. J. Am. Chem. Soc. 1998, 120, 2826. (c) Yabe, T.; Kochi, J. K. J. Am. Chem. Soc. 1992, 114, 4491. (d) Bockman, T. M.; Kochi, J. K. New J. Chem. 1992, 16, 39. (e) Grosso, V. N.; Previtali, C. M.; Chesta, C. A. Photochem. Photobiol. 1998, 68, 481. (f) Marcus, R. A. J. Phys. Chem. B 1998, 102, 10071. (g) Kluge, T.; Knoll, H. Photochem. Photobiol. A 2000, 130, 95. (h) Vakarin, E. V.; Holovko, M. F.; Piotrowiak, P. Chem. Phys. Lett. 2002, 363, 7.
68. For the salt effects on the radical ion pair produced in photoinduced electron transfer, see: (a) Thompson, P. A.; Simon, J. D. J. Am. Chem. Soc. 1993, 115, 5657. (b) Bockman, T. M.; Hubig, S. M.; Kochi, J. K. J. Am. Chem. Soc. 1998, 120, 2826. (c) Yabe, T.; Kochi, J. K. J. Am. Chem. Soc. 1992, 114, 4491. (d) Bockman, T. M.; Kochi, J. K. New J. Chem. 1992, 16, 39. (e) Grosso, V. N.; Previtali, C. M.; Chesta, C. A. Photochem. Photobiol. 1998, 68, 481. (f) Marcus, R. A. J. Phys. Chem. B 1998, 102, 10071. (g) Kluge, T.; Knoll, H. Photochem. Photobiol. A 2000, 130, 95. (h) Vakarin, E. V.; Holovko, M. F.; Piotrowiak, P. Chem. Phys. Lett. 2002, 363, 7.
69. For the salt effects on the radical ion pair produced in photoinduced electron transfer, see: (a) Thompson, P. A.; Simon, J. D. J. Am. Chem. Soc. 1993, 115, 5657. (b) Bockman, T. M.; Hubig, S. M.; Kochi, J. K. J. Am. Chem. Soc. 1998, 120, 2826. (c) Yabe, T.; Kochi, J. K. J. Am. Chem. Soc. 1992, 114, 4491. (d) Bockman, T. M.; Kochi, J. K. New J. Chem. 1992, 16, 39. (e) Grosso, V. N.; Previtali, C. M.; Chesta, C. A. Photochem. Photobiol. 1998, 68, 481. (f) Marcus, R. A. J. Phys. Chem. B 1998, 102, 10071. (g) Kluge, T.; Knoll, H. Photochem. Photobiol. A 2000, 130, 95. (h) Vakarin, E. V.; Holovko, M. F.; Piotrowiak, P. Chem. Phys. Lett. 2002, 363, 7.
70. For the salt effects on the radical ion pair produced in photoinduced electron transfer, see: (a) Thompson, P. A.; Simon, J. D. J. Am. Chem. Soc. 1993, 115, 5657. (b) Bockman, T. M.; Hubig, S. M.; Kochi, J. K. J. Am. Chem. Soc. 1998, 120, 2826. (c) Yabe, T.; Kochi, J. K. J. Am. Chem. Soc. 1992, 114, 4491. (d) Bockman, T. M.; Kochi, J. K. New J. Chem. 1992, 16, 39. (e) Grosso, V. N.; Previtali, C. M.; Chesta, C. A. Photochem. Photobiol. 1998, 68, 481. (f) Marcus, R. A. J. Phys. Chem. B 1998, 102, 10071. (g) Kluge, T.; Knoll, H. Photochem. Photobiol. A 2000, 130, 95. (h) Vakarin, E. V.; Holovko, M. F.; Piotrowiak, P. Chem. Phys. Lett. 2002, 363, 7.
71. (a) Dubois, D.; Moninot, G.; Kutner, W.; Jones, M. T.; Kadish, K. M. J. Phys. Chem. 1992, 96, 7137.
72. (b) Soucaze-Guillous, B.; Kutner, W.; Jones, M. T.; Kadish, K. M. J. Electrochem. Soc. 1996, 143, 550.
73. (a) Savéant, J.-M. J. Phys. Chem. B 2001, 105, 8995.
74. (b) Lehmann, M. W.; Evans, D. H. J. Phys. Chem. B 1998, 102, 9928.
75. (c) Redepenning, J.; Castro-Narro, E.; Venkataraman, G.; Mechalke, E. J. Electroanal. Chem. 2001, 498, 192.
76. Seely, G. R.; Gust, D.; Moore, T. A.; Moore, A. L. J. Phys. Chem. 1994, 98, 10659.
77. (a) Marcus, R. A. Annu. Rev. Phys. Chem. 1964, 15, 155.
78. (b) Marcus, R. A. Angew. Chem., Int. Ed. Engt. 1993, 32, 1111.
79. (c) Marcus, R. A.; Sutin, N. Biochim. Biophys. Acta 1985, 811, 265.
80. Perrin, D. D.; Armarego, W. L. F.; Perrin, D. R., Purification of Laboratory Chemicals, 4th ed.; Pergamon Press: Elmsford, NY, 1996.
81. Bruinink, J.; Kregting, C. G. A.; Ponjee, J. J. J. Electrochem. Soc. 1977, 124, 1854.
82. Fukuzumi, S.; Imahori, H.; Okamoto, K.; Yamada, H.; Fujitsuka, M.; Ho, O.; Guldi, D. M. J. Phys. Chem. A 2002, 106, 1903.
83. (a) Wallenfels, K.; Gellrich, M. Chem. Ber. 1959, 92, 1406.
84. (b) Fukuzumi, S.; Suenobu, T.; Patz, M.; Hirasaka, T.; Itoh, S.; Fujitsuka, M.; Ito, O. J. Am. Chem. Soc. 1998, 120, 8060.
85. Nguyen, K. A.; Day, P. N.; Pachter, R. J. Phys. Chem. A 2000, 104, 4748.
86. •-, see: Fukuzumi, S.; Yorisue, T. J. Am. Chem. Soc. 1991, 113, 7764.
87. 6] gives an apparent linear line because of the fast rate being close to the diffusion.
88. 6.
89. Meites, L. Polarographic Techniques, 2nd ed.; Wiley: New York, 1965; pp 203-301.
90. 2.
91. The ratio of the rate constant of electron transfer at 298 K is given by exp(0.17 × 23060/1.987 × 298) = 750.
92. 4Br are listed in Table S1 (Supporting Information).
93. et vs log[electrolyte].
94. Fukuzumi, S.; Ohkubo, K.; Suenobu, T.; Kato, K.; Fujitsuka, M.; Ito, O. J. Am. Chem. Soc. 2001, 123, 8459.
95. Lewis, F. D.; Hougland, J. L.; Markarian, S. A. J. Phys. Chem. A 2000, 104, 3261.