Mechanism of four-electron reduction of dioxygen to water by ferrocene derivatives in the presence of perchloric acid in benzonitrile, catalyzed by cofacial dicobalt porphyrins

Journal of the American Chemical Society

Volumn 126, Issue 33, 2004, Pages 10441-10449

  Fukuzumi, Shunichi ^a   Okamoto, Ken ^a   Gros, Claude P ^b   Guilard, Roger ^b  

^a OSAKA UNIVERSITY   (Japan)

^b UNIVERSITÉ DE BOURGOGNE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING ENERGY; COUPLED CIRCUITS; ELECTRONS; OXIDATION; PORPHYRINS; TEMPERATURE CONTROL;

DICOBALT PORPHYRINS; DIOXYGEN; MONOCOBALT;

COBALT COMPOUNDS;

BENZONITRILE; COBALT DERIVATIVE; COFACIAL DICOBALT PORPHYRIN DERIVATIVE; FERROCENE DERIVATIVE; IODINE; OXYGEN; PERCHLORIC ACID; PORPHYRIN DERIVATIVE; SUPEROXIDE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; COVALENT BOND; ELECTRON; ELECTRON SPIN RESONANCE; ELECTRON TRANSPORT; OXIDATION; OXIDATION REDUCTION REACTION; REACTION ANALYSIS; REDUCTION; ROOM TEMPERATURE; STRUCTURE ANALYSIS; SUPERHYPERFINE STRUCTURE;

EID: 4143100225     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja048403c     Document Type: Article

References (102)

1. (a) Babcock, G. T.; Wikström, M. Nature 1992, 356, 301.
2. (b) Babcock, G. T. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 12971.
3. (a) Wikström, M.; Krab, K.; Saraste, M. Cytochrome Oxidase: A Synthesis; Academic Press: New York, 1981.
4. (b) Ferguson-Miller, S.; Babcock, G. T. Chem. Rev. 1996, 96, 2889.
5. (a) Einarsdóttir, O. Biochim. Biophys. Acta 1995, 1229, 129.
6. (b) Pereira, M. M.; Santana, M.; Teixeira, M. Biochim. Biophys. Acta 2001, 1505, 185.
7. (c) Zaslavsky, D.; Gennis, R. B. Biochim. Biophys. Acta 2000, 1458, 164.
8. (a) Tsukihara, T.; Aoyama, H.; Yamashita, E.; Tomizaki, T.; Yamaguchi, H.; Shinzawa-Itoh, K.; Nakashima, R.; Yaono, R.; Yoshikawa, S. Science 1995, 269, 1069.
9. (b) Tsukihara, T.; Aoyama, H.; Yamashita, E.; Tomizaki, T.; Yamaguchi, H.; Shinzawa-Itoh, K.; Nakashima, R.; Yaono, R.; Yoshikawa, S. Science 1996, 272, 1136.
10. (c) Yoshikawa, S.; Shinzawa-Itoh, K.; Nakashima, R.; Yaono, R.; Yamashita, E.; Inoue, N.; Yao, M.; Fei, M. J.; Libeu, C. P.; Mizushima, T.; Yamaguchi, H.; Tomizaki, T.; Tsukihara, T. Science 1998, 280, 1723.
11. (a) Iwata, S.; Ostermeier, C.; Ludwig, B.; Michel, H. Nature 1995, 376, 660.
12. (b) Ostermeier, C.; Harrenga, A.; Ermler, U.; Michel, H. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 10547.
13. (c) Yoshikawa, S.; Shinzawa-Itoh, K., Tsukihara, T. J. Inorg. Biochem. 2000, 82, 1.
14. Michel, H.; Behr, J.; Harrenga, A.; Kannt, A. Annu. Rev. Biophys. Biomol. Struct. 1998, 27, 329.
15. Wikström, M. Nature 1977, 266, 271.
16. (a) Sasaki, T.; Naruta, Y. Chem. Lett. 1995, 663.
17. (b) Sasaki, T.; Nakamura, N.; Naruta, Y. Chem. Lett. 1998, 351.
18. (c) Chishiro, T.; Shimazaki, Y.; Tani, F.; Tachi, Y.; Naruta, Y.; Karasawa, S.; Hayami, S.; Maeda, Y. Angew. Chem., Int. Ed. 2003, 42, 2788.
19. Collman, J. P.; Boulatov, R.; Sunderland, C. J. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds; Elsevier Science: USA, 2003; Vol. 11, pp 1-49.
20. (a) Collman, J. P.; Fu, L.; Herrmann, P. C.; Zhang, X. M. Science 1997, 275, 949.
21. (b) Collman, J. P. Inorg. Chem. 1997, 36, 5145.
22. (c) Collman, J. P.; Fu, L.; Herrmann, P. C.; Wang, Z.; Rapta, M.; Bröfing, M.; Schwenninger, R.; Boitrel, B. Angew. Chem., Int. Ed. 1998, 37, 3397.
23. (d) Boulatov, R.; Collman, J. P.; Shiryaeva, I. M.; Sunderland, C. J. J. Am. Chem. Soc. 2002, 124, 11923.
24. (a) Obias, H. V.; van Strijdonck, G. P. F.; Lee, D.-H.; Ralle, M.; Blackburn, N. J.; Karlin, K. D. J. Am. Chem. Soc. 1998, 120, 9696.
25. (b) Ghiladi, R. A.; Ju, T. D.; Lee, D.-H.; Moënne-Loccoz, P.; Kaderli, S.; Neuhold, Y.-M.; Zuberbühler, A. D.; Woods, A. S.; Cotter, R. J.; Karlin, K. D. J. Am. Chem. Soc. 1999, 121, 9885.
26. (c) Ghiladi, R. A.; Hatwell, K. R.; Karlin, K. D.; Huang, H.-w.; Moënne-Loccoz, P.; Krebs, C.; Huynh, B. H.; Marzilli, L. A.; Cotter, R. J.; Kaderli, S.; Zuberbühler, A. D. J. Am. Chem. Soc. 2001, 123, 6183.
27. (d) Liang, H. C.; Dahan, M.; Karlin, K. D. Curr. Opin. Chem. Biol. 1999, 3, 168.
28. (a) Baeg, J.-O.; Holm, R. H. Chem. Commun. 1998, 571.
29. (b) Lim, B. S.; Holm, R. H. Inorg. Chem. 1998, 37, 4898.
30. (a) Collman, J. P.; Rapta, M.; Bröring, M.; Raptova, L.; Schwenninger, R.; Boitrel, B.; Fu, L.; L'Her, M. J. Am. Chem. Soc. 1999, 121, 1387.
31. (b) Collman, J. P.; Boulatov, R. Angew. Chem., Int. Ed. 2002, 41, 3487.
32. Anson, F. C.; Shi, C. N.; Steiger, B. Acc. Chem. Res. 1997, 30, 437.
33. (a) Kingsborough, R. P.; Swager, T. M. Chem. Mater. 2000, 12, 872.
34. (b) Kingsborough, R. P.; Swager, T. M. Adv. Mater. 1998, 10, 1100.
35. (c) Vijayalatha, S.; Gomathi, H.; Prabhakara, R. Bull. Electrochem. 1992, 8, 222.
36. (a) Rywkin, S.; Hosten, C. M.; Lombardi, J. R.; Birke, R. L. Langmuir 2002, 18, 5869.
37. (b) Bouwkamp-Wijnoltz, A. L.; Visscher, W.; van Veen, J. A. R.; Boellaard, E.; van der Kraan, A. M.; Tang, S. C. J. Phys. Chem. B 2002, 106, 12993.
38. (a) Liu, Z.; Anson, F. C. Inorg. Chem. 2001, 40, 1329.
39. (b) Liu, Z.; Anson, F. C. Inorg. Chem. 2000, 39, 274.
40. (c) Yamamoto, K.; Oyaizu, K.; Tsuchida, E. J. Am. Chem. Soc. 1996, 118, 12665.
41. 2. See: (a) Collman, J. P.; Fudickar, W.; Shiryaeva, I. Inorg. Chem. 2003, 42, 3384.
42. (b) Reference 10d.
43. 2 in such a way that the cleavage of the O-O bond occurs. See: (a) Ricard, D.; Andrioletti, B.; L'Her, M.; Boitrel, B. Chem. Commun. 1999, 1523.
44. (b) Ricard, D.; L'Her, M.; Richard, P.; Boitrel, B. Chem.-Eur. J. 2001, 7, 3291.
45. (c) Didier, A.; L'Her, M.; Boitrel, B. Org. Biomol. Chem. 2003, 1, 1274.
46. (a) Shigehara, K.; Anson, F. C. J. Phys. Chem. 1982, 86, 2776.
47. (b) Bouwkamp-Wijnoltz, A. L.; Visscher, W.; van Veen, J. A. R. Electrochim. Acta 1998, 43, 3141.
48. (c) Xuan Zheng, W.; Yi Jun, L.; Bernd, G.; Nai Teng, Y.; Reinhard, R. Electroanalysis 1997, 9, 1288.
49. (d) Wan, G.-X.; Shigehara, K.; Tsuchida, E.; Anson, F. C. J. Electroanal. Chem. Interfacial Electrochem. 1984, 179, 239.
50. (e) Kobayashi, N.; Osa, T. J. Electroanal. Chem. Interfacial Electrochem. 1983, 157, 269.
51. (a) Chang, C. K.; Abdalmuhdi, I. Angew. Chem., Int. Ed. Engl. 1984, 23, 164.
52. (b) Chang, C. K.; Liu, H. Y.; Abdalmuhdi, I. J. Am. Chem. Soc. 1984, 106, 2725.
53. (a) Collman, J. P.; Hutchison, J. E.; Lopez, M. A.; Tabard, A.; Guilard, R.; Seok, W. K.; Ibers, J. A.; L'Her, M. J. Am. Chem. Soc. 1992, 114, 9869.
54. (b) Collman, J. P.; Wagenknecht, P. S.; Hutchison, J. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 1537.
55. (c) Collman, J. P.; Denisevich, P.; Konai, Y.; Marrocco, M.; Koval, C.; Anson, F. C. J. Am. Chem. Soc. 1980, 102, 6027.
56. (a) Deng, Y.; Chang, C. J.; Nocera, D. G. J. Am. Chem. Soc. 2000, 122, 410.
57. (b) Chang, C. J.; Deng, Y.; Shi, C.; Chang, C. K.; Anson, F. C.; Nocera, D. G. Chem. Commun. 2000, 1355.
58. (c) Le Mest, Y.; Inisan, M.; Laouénan, A.; L'Her, M.; Talarmin, J.; El Khalifa, M. E.; Saillard, J.-Y. J. Am. Chem. Soc. 1997, 119, 6095.
59. (d) Steiger, B.; Anson, F. C. Inorg. Chem. 2000, 39, 4579.
60. (e) Zou, S.; Clegg, R. S.; Anson, F. C. Langmuir 2002, 18, 3241.
61. D'Souza, F.; Hsieh, Y.-Y.; Deviprasad, G. R. Chem. Commun. 1998, 1027.
62. 2 in a homogeneous solution, see: (a) Fukuzumi, S.; Mochizuki, S.; Tanaka, T. Inorg. Chem. 1989, 28, 2459.
63. (b) Fukuzumi, S.; Mochizuki, S.; Tanaka, T. Inorg. Chem. 1990, 29, 653.
64. (c) Anson, F. C.; Ni, C.-L.; Saveant, J.-M. J. Am. Chem. Soc. 1985, 107, 3442.
65. 2 adduct was fully reduced to the deoxygenated form with 4 equiv of cobaltocene. See also: Collman, J. P.; Herrmann, P. C.; Boitrel, B.; Zhang, X.; Eberspacher, T. A.; Fu, L.; Wang, J. L.; Rousseau, D. L.; Williams, E. R. J. Am. Chem. Soc. 1994, 116, 9783.
66. Guilard, R.; Lopez, M. A.; Tabard, A.; Richard, P.; Lecomte, C.; Brandès, S.; Hutchison, J. E.; Collman, J. P. J. Am. Chem. Soc. 1992, 114, 9877.
67. Chang, C. J.; Deng, Y.; Heyduk, A. F.; Chang, C. K.; Nocera, D. G. Inorg. Chem. 2000, 39, 959.
68. Van Leusen, A. M.; Schaart, F. J.; Van Leusen, D. Recl. J. R. Neth. Chem. Soc. 1979, 98, 258.
69. Perrin, D. D.; Armarego, W. L. F.; Perrin, D. R. Purification of Laboratory Chemicals, 4th ed.; Pergamon Press: Elmsford, NY, 1996.
70. DeSimone, R. E.; Drago, R. S. J. Am. Chem. Soc. 1970, 92, 2343.
71. Mair, R. D.; Graupner, A. J. Anal. Chem. 1964, 36, 194.
72. Fukuzumi, S.; Kuroda, S.; Tanaka, T. J. Am. Chem. Soc. 1985, 107, 3020.
73. (a) Fukuzumi, S.; Imahori, H.; Yamada, H.; El-Khouly, M. E.; Fujitsuka, M.; Ito, O.; Guldi, D. M. J. Am. Chem. Soc. 2001, 123, 2571.
74. (b) Fukuzumi, S.; Ishikawa, M.; Tanaka, T. J. Chem. Soc., Perkin Trans. 2 1989, 1037.
75. 4 to a air-saturated PhCN solution of Co(II)(OEP). See: Setsune, J.; Saito, Y.; Ishimaru, M.; Ikeda, M.; Kitao, T. Bull. Chem. Soc. Jpn. 1992, 65, 639.
76. For the electron-transfer oxidation of Co(II) porphyrins to Co(III) porphyrins, see: (a) Fukuzumi, S.; Ohkubo, K. Chem.-Eur. J. 2000, 6, 4532.
77. (b) Fukuzumi, S.; Kitaguchi, H.; Suenobu, T.; Ogo, S. Chem. Commun. 2002, 1984.
78. (a) Chang, C. K. J. Chem. Soc., Chem. Commun. 1977, 800.
79. (b) Le Mest, Y.; L'Her, M.; Courtot-Coupez, J.; Collman, J. P.; Evitt, E. R.; Bencosme, C. S. J. Chem. Soc., Chem. Commun. 1983, 1286.
80. (c) Guilard, R.; Jérôme, F.; Gros, C. P.; Barbe, J.-M.; Ou, Z.; Shao, J.; Kadish, K. M. C. R. Acad. Sci., Ser. IIc: Chim. 2001, 4, 245.
81. Mann, C. K.; Barnes, K. K. Electrochemical Reactions in Nonaqueous Systems; Marcel Dekker: New York, 1990.
82. 2(DPD) have been reported previously in different conditions. See: ref 23b and c.
83. (a) Dolphin, D.; Forman, A.; Borg, D. C.; Fajer, J.; Felton, R. H. Proc. Natl. Acad. Sci. U.S.A. 1971, 68, 614.
84. (b) Felton, R. H.; Dolphin, D.; Borg, D. C.; Fajer, J. J. Am. Chem. Soc. 1969, 91, 196.
85. The first oxidation of a Co(II) porphyrin in a noncoordinating solvent involves formation of a Co(II) porphyrin radical cation, whereas the first oxidation in potentially coordinating solvents invariably involves the metal-centered oxidation to produce a Co(III) porphyrin. See: (a) Salehi, A.; Oertling, W. A.; Babcock, G. T.; Chang, C. K. J. Am. Chem. Soc. 1986, 108, 5630.
86. (b) Kadish, K. M.; Lin, X. Q.; Han, B. C. Inorg. Chem. 1987, 26, 4161.
87. (a) Le Mest, Y.; L'Her, M.; Collman, J. P.; Kim, K.; Hendricks, N. H.; Helm, S. J. Electroanal. Chem. 1987, 234, 277.
88. (b) Kadish, K. M.; Guo, N.; Van Caemelbecke, E.; Paolesse, R.; Monti, D.; Tagliatesta, P. J. Porphyrins Phthalocyanines 1998, 2, 439.
89. (a) Marcus, R. A. Annu. Rev. Phys. Chem. 1964. 15, 155.
90. (b) Marcus, R. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1111.
91. (c) Eberson, L. Adv. Phys. Org. Chem. 1982, 18, 79.
92. 2 between the two cobalt atoms of cofacial dicobalt porphyrins with an appropriate cobalt-cobalt separation.
93. However, it should be noted that the thermodynamic stability is not necessarily related directly with the kinetic reactivity.
94. Bolze, F.; Gros, C. P.; Drouin, M.; Espinosa, E.; Harvey, P. D.; Guilard, R. J. Organomet. Chem. 2002, 643-644, 89.
95. Chang, C. I.; Baker, E. A.; Pistorio, B. I.; Deng, Y.; Loh, Z.-H.; Miller, S. E.; Carpenter, S. D.; Nocera, D. G. Inorg. Chem. 2002, 41, 3102.
96. The flexibility of the DPD spacer allows us to shorten the metal-metal separation, resulting in forming the μ-oxo species; ref 47.
97. Although the formation of the Co(III)-Co(IV) intermediate is energetically uphill, the followup rapid electron transfer from ferrocene derivatives makes the process energetically feasible. Formation of a high-valent cobalt-oxo complex has been suggested. See: Nam, W.; Kim, I.; Kim, Y.; Kim, C. Chem. Commun. 2001, 1296.
98. (a) Sono, M.; Roach, M. P.; Coulter, E. D.; Dawson, J. H. Chem. Rev. 1996, 96, 2841.
99. (b) Poulos, T. L. In The Porphyrin Handbook; Kadish, K. M.; Smith, K. M., Guilard, R., Ed.; Academic Press: San Diego, CA, 2000; Vol. 4, pp 189-218.
100. Loew, G. H.; Harris, D. L. Chem. Rev. 2000, 100, 407.
101. Nicholls, P.; Fita, I.; Loewen, P. C. Adv. Inorg. Chem. 2001, 51, 51.
102. de Momtellano, P. R. O. Cytochrome P450, 2nd ed.; Plenum: New York, 1995.