Proton-coupled electron transfer of ruthenium(III)-Pterin complexes: A mechanistic insight

Journal of the American Chemical Society

Volumn 131, Issue 32, 2009, Pages 11615-11624

  Miyazaki, Soushi ^a   Kojima, Takahiko ^a,c   Mayer, James M ^b   Fukuzumi, Shunichi ^a  

^a OSAKA UNIVERSITY   (Japan)

^b UNIVERSITY OF WASHINGTON   (United States)

^c UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

4-NITROPHENOL; ACTIVATION ENTHALPIES; ACTIVATION PARAMETER; ADDUCT FORMATION; AMINO GROUP; AS-LIGANDS; ASSOCIATIVE MECHANISMS; BOND DISSOCIATION ENERGIES; ELECTRON TRANSFER; HYDROGEN BONDINGS; HYDROGEN-ATOM TRANSFER; INTERMOLECULAR HYDROGEN BONDING; LINEAR RELATIONSHIPS; LOW TEMPERATURES; MULTI-STEP; PHENOL DERIVATIVES; PROTON-COUPLED ELECTRON TRANSFER; REDOX-ACTIVE; RUTHENIUM COMPLEXES; SATURATION BEHAVIOR; SECOND-ORDER RATE CONSTANTS; THERMODYNAMIC PARAMETER; TWO-POINT;

ACETONITRILE; AMINES; COMPRESSED AIR MOTORS; ELECTRON TRANSITIONS; HYDROGEN; HYDROGEN BONDS; LIGANDS; LUMINESCENCE OF ORGANIC SOLIDS; PHENOLS; PLATINUM COMPOUNDS; PROTON TRANSFER; PROTONS; RATE CONSTANTS; RUTHENIUM; RUTHENIUM COMPOUNDS;

SUBSTRATES;

4 NITROPHENOL; ACETONITRILE; HYDROGEN; OXYGEN; PHENOL DERIVATIVE; PROTON; PTERIN; RUTHENIUM;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; ELECTROCHEMISTRY; ELECTRON TRANSPORT; ENTHALPY; LOW TEMPERATURE; OXIDATION REDUCTION REACTION; PROTON TRANSPORT; SPECTROSCOPY; THERMODYNAMICS;

ELECTRON TRANSPORT; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PROTONS; PTERINS; RUTHENIUM COMPOUNDS; THERMODYNAMICS;

EID: 68849093453     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja904386r     Document Type: Article

References (85)

1. (a) Paddock, M. L.; Feher, G.; Okamura, M. Y. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 1548-1553.
2. (b) Feher, G. Photosynth. Res. 1998, 55, 3-40.
3. Alberts, B.; Bray, D.; Lewis, J.; Raff, M.; Roberts, K.; Watson, J. D. Molecular Biology of the Cell, 3rd ed.; Garland Publishing: New York, 1994; pp 71-72 and pp 663-665.
4. (a) Huynh, M. H. V.; Meyer, T. J. Chem. Rev. 2007, 107, 5004-5064.
5. (b) Stubbe, J.; van der Donk, W. A. Chem. Rev. 1998, 98, 705-762.
6. (a) Cukier, R. I.; Nocera, D. G. Annu. Rev. Phys. Chem. 1998, 49, 337-369.
7. (b) Stubbe, J.; Nocera, D. G.; Yee, C. S.; Chang, M. C. Y. Chem. Rev. 2003, 103, 2167-2201.
8. (c) Chang, C. J.; Chang, M. C. Y.; Damrauer, N. H.; Nocera, D. G. Biochim. Biophys. Acta 2004, 1655, 13-28.
9. (a) Mayer, J. M. Annu. Rev. Phys. Chem. 2004, 55, 363-390.
10. (b) Mayer, J. M.; Rhile, I. J. Biochim. Biophys. Acta 2004, 1655, 51-58.
11. (a) Fukuzumi, S. Prog. Inorg. Chem. 2009, 56, 49-153.
12. (b) Fukuzumi, S. Bull. Chem. Soc. Jpn. 1997, 70, 1-28.
13. (c) Fukuzumi, S.; Ishikawa, K.; Hironaka, K.; Tanaka, T. J. Chem. Soc., Perkin Trans. 2 1987, 751-760.
14. (a) Hatcher, E.; Soudackov, A. V.; Hammes-Schiffer, S. J. Am. Chem. Soc. 2004, 126, 5763-5775.
15. (b) Lehnert, N.; Solomon, E. I. J. Biol. Inorg. Chem. 2003, 8, 294-305.
16. (c) Goldsmith, C. R.; Stack, T. D. P. Inorg. Chem. 2006, 45, 6048-6055.
17. (d) Fukuzumi, S. Helv. Chim. Acta 2006, 89, 2425-2439.
18. Bordwell, F. G.; Cheng, J.-P.; Ji, G.-Z.; Satish, A. V.; Zhang, X. J. Am. Chem. Soc. 1991, 113, 9790-9795.
19. Mader, E. A.; Larsen, A. S.; Mayer, J. M. J. Am. Chem. Soc. 2004, 126, 8066-8067.
20. Roth, J. P.; Yoder, J. C.; Won, T.-J.; Mayer, J. M. Science 2001, 294, 2524-2526.
21. (a) Waidmann, C. R.; Zhou, X.; Tsai, E. A.; Kaminsky, W.; Hrovat, D. A.; Borden, W. T.; Mayer, J. M. J. Am. Chem. Soc. 2009, 131, 4729-4743.
22. (b) Wu, A.; Mayer, J. M. J. Am. Chem. Soc. 2008, 130, 14745-14754.
23. (a) Fukuzumi, S. In Advances in Electron Transfer Chemistry; Mariano, P. S., Ed.; JAI Press: Greenwich, CT, 1992; pp 67-175.
24. (b) Fukuzumi, S.; Tanaka, T. In Photoinduced Electron Transfer; Fox, M. A., Chanon, M., Eds.; Elsevier: Amsterdam, 1988; Part C, Chapter 10, pp 578-635.
25. (c) Fukuzumi, S.; Koumitsu, S.; Hironaka, K.; Tanaka, T. J. Am. Chem. Soc. 1987, 109, 305-316.
26. (a) De Colibus, L.; Mattevi, A. Curr. Opin. Struct. Biol. 2006, 16, 722-728.
27. (b) Alberts, B.; Bray, D.; Lewis, J.; Raff, M.; Roberts, K.; Watson, J. D. Molecular Biology of the Cell, 3rd ed.; Garland Publishing: New York, 1994; pp 659-662.
28. (a) Tollin, G. In Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, 2001; Vol. 5, pp 202-231.
29. (b) Fukuzumi, S.; Tanaka, T. In Photoinduced Electron Transfer; Fox, M. A., Chanon, M., Eds.; Elsevier: Amsterdam, 1988; Part C, pp 636-687.
30. (a) Bobst, A. M. Nature 1968, 220, 164-165.
31. (b) Mastropaolo, D.; Camerman, A.; Camerman, N. Science 1980, 210, 334-336.
32. (a) Fukuzumi, S.; Tanii, K.; Tanaka, T. J. Chem. Soc., Chem. Commun. 1989, 816-818.
33. (b) Fukuzumi, S.; Tanii, K.; Tanaka, T. Chem. Lett. 1989, 35-38.
34. (a) Burgmayer, S. J. N. Struct. Bonding (Berlin) 1998, 92, 67-119.
35. (b) Benkovic, S. J.; Sammons, D.; Armarego, W. L. F.; Waring, P.; Inners, R. J. Am. Chem. Soc. 1985, 107, 3706-3712.
36. (c) Raghavan, R.; Dryhurst, G. J. Electroanal. Chem. 1981, 129, 189-212.
37. (d) Bobst, A. Helv. Chim. Acta 1967, 50, 2222-2225.
38. (a) Hille, R. Chem. Rev. 1996, 96, 2757-2816.
39. (b) Anderson, O. A.; Flatmark, T.; Hough, E. J. Mol. Biol. 2002, 320, 1095-1108.
40. (c) Anderson, O. A.; Flatmark, T.; Hough, E. J. Mol. Biol. 2001, 314, 279-291.
41. (d) Erlandsen, H.; Bjørgo, E.; Flatmark, T.; Stevens, R. C. Biochemistry 2000, 39, 2208-2217.
42. (e) Kappock, T. J.; Caradonna, J. P. Chem. Rev. 1996, 96, 2659-2756.
43. (f) Raman, C. S.; Li, H.; Martásek, P.; Král, V.; Masters, B. S. S.; Poulos, T. L. Cell 1998, 95, 939-950.
44. (g) Crane, B. R.; Arval, A. S.; Ghosh, D. K.; Wu, C.; Getzoff, E. D.; Stuehr, D. J.; Tainer, J. A. Science 1998, 279, 2121-2126.
45. (h) Aoyagi, M.; Arval, A. S.; Ghosh, D. K.; Stuehr, D. J.; Tainer, J. A.; Getzoff, E. D. Biochemistry 2001, 40, 12826-12832.
46. Kaim, W.; Schwederski, B.; Heilmann, O.; Hornung, F. M. Coord. Chem. Rev. 1999, 182, 323-342.
47. Abelleira, A.; Galang, R. D.; Clarke, M. J. Inorg. Chem. 1990, 29, 633-639.
48. Miyazaki, S.; Ohkubo, K.; Kojima, T.; Fukuzumi, S. Angew. Chem., Int. Ed. 2008, 47, 9669-9672.
49. (a) Miyazaki, S.; Kojima, T.; Sakamoto, T.; Matsumoto, T.; Ohkubo, K.; Fukuzumi, S. Inorg. Chem. 2008, 47, 333-343.
50. (b) Fukuzumi, S.; Kojima, T. J. Biol. Inorg. Chem. 2008, 13, 321-333.
51. Kojima, T.; Sakamoto, T.; Matsuda, Y.; Ohkubo, K.; Fukuzumi, S. Angew. Chem., Int. Ed. 2003, 42, 4951-4954.
52. Armarego, W. L. F.; Chai, C. L. L. Purification of Laboratory Chemicals, 5th ed.; Butterworth-Heinemann: Oxford, UK, 2003.
53. Goldsmith, C. R.; Jonas, R. T.; Stack, T. D. P. J. Am. Chem. Soc. 2002, 235, 83-96.
54. (a) Izutsu, K. Acid-Base Dissociation Constants in Dipolar Aprotic Solvents; Blackwell Scientific: Boston, MA, 1990.
55. (b) Coetzee, J. F.; Padmanabhan, G. R. J. Phys. Chem. 1965, 69, 3193-3196.
56. Felton, G. A. N.; Glass, R. S.; Lichtenberger, D. L.; Evans, D. H. Inorg. Chem. 2006, 45, 9181-9184.
57. (a) Parker, V. D.; Handoo, K. L.; Roness, F.; Tilset, M. J. Am. Chem. Soc. 1991, 113, 7493-7498.
58. (b) Wayner, D. D. M.; Parker, V. D. Acc. Chem. Res. 1993, 26, 287-294.
59. (c) Skagestad, V.; Tilset, M. J. Am. Chem. Soc. 1993, 115, 5077-5083.
60. (d) Tilset, M.; Parker, V. D. J. Am. Chem. Soc. 1989, 111, 6711-6717.
61. Tilset, M. In Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 2, pp 677-713.
62. (a) Wu, A.; Mayer, J. M. J. Am. Chem. Soc. 2008, 130, 14745-14754.
63. (b) Mader, E. A.; Manner, V. W.; Markle, T. F.; Wu, A.; Franz, J. A.; Mayer, J. M. J. Am. Chem. Soc. 2009, 131, 4335-4345.
64. Rhile, I. J.; Markle, T. F.; Nagao, H.; DiPasquale, A. G.; Lam, O. P.; Lockwood, M. A.; Rotter, K.; Mayer, J. M. J. Am. Chem. Soc. 2006, 128, 6075-6088.
65. Fukuzumi, S.; Wong, C. L.; Kochi, J. K. J. Am. Chem. Soc. 1980, 102, 2928-2939.
66. 3), 500 (2.1 × 103).
67. Wright, J. S.; Johnson, E. R.; DiLabio, G. A. J. Am. Chem. Soc. 2001, 123, 1173-1183.
68. The lack of ESR signals in the reaction mixtures including other phenols suggests the formation of diamagnetic coupling products.
69. Mader, E. A.; Davidson, E. R.; Mayer, J. M. J. Am. Chem. Soc. 2007, 129, 5153-5166.
70. Foti, M. C.; Daquino, C.; Mackie, I. D.; DiLabio, G. A.; Ingold, K. U. J. Org. Chem. 2008, 73, 9270-9282.
71. Kwart, H. Acc. Chem. Res. 1982, 15, 401-408.
72. Pratt, R. P.; Stack, T. D. Prog. Inorg. Chem. 2005, 44, 2367-2375.
73. Fecenko, C. J.; Thorp, H. H.; Meyer, T. J. J. Am. Chem. Soc. 2007, 129, 15098-15099.
74. Bordwell, F. G.; Cheng, J.-P. J. Am. Chem. Soc. 1991, 113, 1736-1743.
75. Marcus, R. A.; Sutin, N. Biochim. Biophys. Acta 1985, 811, 265-322.
76. For RudO: (a) Che, C.-M.; Tang, W.-T.; Wong, K.-W.; Li, C.-K. J. Chem. Soc., Dalton Trans. 1991, 3277-3280.
77. (b) Seok, W. K.; Meyer, T. J. J. Am. Chem. Soc. 1988, 110, 7358-7367.
78. For FedO: (c) Kaizer, J.; Klinker, E. J.; Oh, N. Y.; Rohde, J.-U.; Song, W. J.; Stubna, A.; Kim, J.; Münck, E.; Nam, W.; Que, L., Jr. J. Am. Chem. Soc. 2004, 126, 472-473.
79. Yiu, D. T. Y.; Lee, M. F. W.; Lam, W. W. Y.; Lau, T. C. Inorg. Chem. 2003, 42, 1225-1232.
80. Napolitano, A.; Palumbo, A.; d'Ischia, M. Tetrahedron 2000, 56, 5941-5945.
81. See, for instance: (a) Valgimigli, L.; Banks, J. T.; Ingold, K. U.; Lusztyk, J. J. Am. Chem. Soc. 1995, 117, 9966-71.
82. (b) Snelgrove, D. W.; Lusztyk, J.; Banks, J. T.; Mulder, P.; Ingold, K. U. J. Am. Chem. Soc. 2001, 123, 469-477.
83. (a) Yiu, D. T. Y.; Lee, M. F. W.; Lam, W. W. Y.; Lau, T.-C. Inorg. Chem. 2003, 42, 1225-1232.
84. (b) Lam, W. W. Y.; Man, W.-L.; Lau, T.-C. Coord. Chem. Rev. 2007, 251, 2238-2252.
85. 37