Electrochemical insights into the mechanisms of proton reduction by [Fe2(CO)6(μ-SCH2N(R)CH2S)] complexes related to the [2Fe]H subsite of [FeFe]hydrogenase

Chemistry - A European Journal

Volumn 14, Issue 6, 2008, Pages 1954-1964

  Capon, Jean François ^a   Ezzaher, Salah ^a   Gloaguen, Frédéric ^a   Pétition, François Y ^a   Schollhammer, Philippe ^a   Talarmin, Jean ^a  

^a UNIVERSITÉ DE BRETAGNE OCCIDENTALE   (France)

Author keywords

Bioinorganic chemistry; Electrochemistry; Iron; Proton reduction; S ligands

Indexed keywords

BIOCHEMISTRY; ELECTROCHEMISTRY; IRON;

ACID CONCENTRATIONS; BIOINORGANIC CHEMISTRY; ELECTROCHEMICAL INVESTIGATIONS; PROTON REDUCTION; REDUCTION POTENTIAL; S LIGANDS; STRUCTURAL ANALOGUE; [FEFE]HYDROGENASES;

REDUCTION;

HYDROGENASE; IRON DERIVATIVE; IRON HYDROGENASE; IRON SULFUR PROTEIN; PROTON;

ARTICLE; ELECTROCHEMISTRY; METABOLISM; METHODOLOGY;

ELECTROCHEMISTRY; HYDROGENASE; IRON COMPOUNDS; IRON-SULFUR PROTEINS; PROTONS;

EID: 44349159402     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200701454     Document Type: Article

References (115)

1. a) J. W. Peters, W. N. Lanzilotta, B. J. Lemon, L. C. Seefeldt, Science 1998, 282, 1853-1858;
2. b) B. J. Lemon, J. W. Peters, Biochemistry 1999, 38, 12969-12973.
3. a) Y. Nicolet, C. Piras, P. Legrand, C. E. Hatchikian, J. C. Fontecilla-Camps. Structure 1999, 7, 13-23;
4. b) Y. Nicolet, A. L. de Lacey, X. Vernede, V. M. Fernandez, C. E. Hatchikian, J. C. Fontecilla-Camps, J. Am. Chem. Soc. 2001, 123, 1596-1602.
5. For recent reviews, see: a) I. P. Georgakaki, L. M. Thomson, E. J. Lyon, M. B. Hall, M. Y. Darensbourg, Coord. Chem. Rev. 2003, 238-239, 255-266;
6. b) M. Y. Darensbourg, E. J. Lyon, X. Zhao, I. P. Georgakaki, Proc. Natl. Acad. Sci. USA 2003, 100, 3683-3688;
7. c) D. J. Evans, C. J. Pickett, Chem. Soc. Rev. 2003, 32, 268-275;
8. d) T. B. Rauchfuss, Inorg. Chem. 2004, 43, 14-26;
9. e) L.-C. Song, Acc. Chem. Res. 2005, 38, 21-28;
10. f) V. Artero, M. Fontecave, Coord. Chem. Rev. 2005, 249, 1518-1535;
11. g) S. P. Best, Coord. Chem. Rev. 2005, 249, 1536-1554;
12. h) M. Bruschi, G. Zampella, P. Fanlucci, L. De Gioia, Coord. Chem. Rev. 2005, 249, 1620-1640;
13. i) X. Liu, S. K. Ibrahim, C. Tard, C. J. Pickett, Coord. Chem. Rev. 2005, 249, 1641-1652;
14. j) L. Sun, B. Akermark, S. Oil. Coord. Chem. Rev. 2005, 249, 1653-1663;
15. k) J.-F. Capon, F. Gloaguen, P. Schollhammer, J. Talarmin, Coord. Chem. Rev. 2005, 249, 1664-1676. and references therein.
16. 2ases is provided as Supporting Information.
17. a) F. Gloaguen, J. D. Lawrence, T. B. Rauchfuss, J. Am. Chem. Soc. 2001, 123, 9476-9477;
18. b) F. Gloaguen, J. D. Lawrence, T. B. Rauchfuss, M. Bénard, M.-M. Rohmer, Inorg. Chem. 2002, 41, 6573-6582.
19. a) X. Zhao, I. P. Georgakaki, M. L. Miller, J. C. Yarbrough, M. Y. Darensbourg, J. Am. Chem. Soc. 2001, 123, 9710-9711;
20. b) X. Zhao, I. P. Georgakaki, M. L. Miller, R. Mejia-Rodriguez, C.-H. Chiang, M. Y. Darensbourg, Inorg. Chem. 2002, 41, 3917-3928.
21. a) J.-F. Capon, S. El Hassnaoui, F. Gloaguen, P. Schollhammer, J. Talarmin, Organometallics 2005, 24, 2020-2022;
22. b) D. Morvan, J.-F. Capon, F. Gloaguen, A. Le Goff, M. Marchivie, F. Michaud, P. Schollhammer, J. Talarmin, J.-J. Yaouanc, R. Pichon, N. Kervarec, Organometallics 2007, 26. 2042-2052;
23. c) F. Gloaguen, D. Morvan, J.-F. Capon, P. Schollhammer, J. Talarmin, J. Electroanal. Chem. 2007, 603, 15-20;
24. d) S. Ezzaher, J.-F. Capon, F. Gloaguen, F. Y. Pétition, P. Schollhammer, J. Talarmin, R. Pichon, N. Kervarec, Inorg. Chem., 2007, 46, 3426-3428.
25. a) W. Dong, M. Wang, X. Liu, G. Li, F. Wang, L. Sun, Chem. Commun. 2006, 305-307;
26. b) W. Dong, M. Wang, T. Liu, X. Liu, K. Jin, L. Sun, J. Inorg. Biochem. 2007, 101, 506-513;
27. c) S. Jiang, J. Liu. Z. Wang, B. Åkermark, L. Sun, Polyhedron 2007, 26, 1499-1504.
28. a) G. Hogarth, I. Richards, Inorg. Chem. Commun. 2007, 10, 66-70;
29. b) F. I. Adam, G. Hogarth, I. Richards, J. Organomet. Chem. 2001, 692, 3957-3968.
30. J. L. Nehring, D. M. Heinekey, Inorg. Chem. 2003, 42, 4288-4292.
31. K. Fauvel, R. Mathieu, R. Poilblanc, Inorg. Chem. 1976, 15, 976-978.
32. R. Mejia-Rodriguez, D. Chong, J. H. Reibenspies, M. P. Soriaga, M. Y. Darensbourg, J. Am. Chem. Soc. 2004, 126, 12004-12014.
33. a) J. D. Lawrence, H. Li, T. B. Rauchfuss, M. Bénard, M.-M. Rohmer, Angew. Chem. Int. Ed. 2001, 40, 1768-1771;
34. b) H. Li, T. B. Rauchfuss, J. Am. Chem. Soc. 2002, 124, 726-727.
35. a) S. Ott, M. Kritikos, B. Åkermark, L. Sun, R. Lomoth, Angew. Chem. Int. Ed. 2004, 43, 1006-1009;
36. b) F. Wang, M. Wang, X. Liu, K. Jin, W. Dong, G. Li, B. Åkermark, L. Sun, Chem. Commun. 2005, 3221-3223;
37. c) S. Jiang, J. Liu, L. Sun, Inorg. Chem. Commun. 2006, 9, 290-292;
38. d) W. Gao, J. Liu, B. Åkermark, L. Sun, Inorg. Chem. 2006, 45, 9169-9171;
39. e) W. Gao, J. Liu, C. Ma, L. Weng, K. Jin, C. Chen, B. Åkermark, L. Sun, Inorg. Chim. Acta 2006, 359, 1071-1080;
40. f) S. Jiang, J. Liu, Y. Shi, Z. Wang, B. Åkermark, L. Sun, Dalton Trans. 2007, 896-902;
41. g) W. Gao, J. Ekström, J. Liu, C. Chen, L. Eriksson, L. Weng, B. Åkermark, L. Sun, Inorg. Chem. 2007, 46, 1981-1991.
42. a) L.-C. Song, J.-H. Ge, X.-F. Liu, L.-Q. Zhao, Q.-M. Hu, J. Organomet. Chem. 2006, 691, 5701-5709;
43. b) L.-C. Song, J.-H. Ge, X.-G. Zhang, Y. Liu, Q.-M. Hu, Eur. J. Inorg. Chem. 2006, 3204-3210.
44. a) A. L. De Lacey, V. M. Fernandez, M. Rousset, R. Cammack, Chem. Rev. 2007, 107, 4304-4330;
45. b) W. Lubitz, E. Reijerse, M. van Gaste., Chem. Rev. 2007, 107, 4331-4365. and references therein.
46. a) Y. Nicolet, A. L. de Lacey, X. Vernede, V. M. Fernandez, C. E. Hatchikian, J. C. Fontecilla-Camps, J. Am. Chem. Soc. 2001, 123, 1596-1602;
47. b) Y. Nicolet, B. J. Lemon, J. C. Fonlecilla-Camps, J. W. Peters. Trends Biochem. Sci. 2000, 25, 138-143;
48. c) Y. Nicolet, C. Cavazza, J. C. Fontecilla-Camps, J. Inorg. Biochem. 2002, 91, 1-8.
49. a) R. H. Crabtree, J. A. Loch, K. Gruet, D.-H. Lee, C. Borgmann, J. Organomet. Chem. 2000, 600, 7-11;
50. b) R. H. Crabtree, P. E. M. Siegbahn, O. Eisenstein, A. L. Rheingold, T. F. Koetzle, Acc. Chem. Res. 1996, 29, 348-354;
51. c) E. Peris, J. C. Lee, Jr., J. R. Rambo, O. Eisenstein, R. H. Crabtree, J. Am. Chem. Soc. 1995, 117, 3485-3491;
52. d) J. C. Lee, E. Peris, A. L. Rheingold, R. H. Crabtree, J. Am. Chem. Soc. 1994, 116, 11014-11019.
53. A. J. Lough, S. Park, R. Ramachandran, R. H. Morris, J. Am. Chem. Soc. 1994, 116, 8356-8357.
54. H. S. Shu, C. P. Lau, K. Y. Wong, W. T. Wong, Organometallics 1998, 17, 2768-2777.
55. J. A. Ayllon, S. F. Sayers, S. Sabo-Etienne, B. Donnadieu, B. Chaudret, E. Clot, Organometallics 1999, 18, 3981-3990, and references therein.
56. F. A. Jalon, B. R. Manzano, A. Caballero, M. C. Carrion, L. Santos, G. Espino, M. Moreno, J. Am. Chem. Soc. 2005, 127, 15364-15365.
57. a) C. J. Curtis, A. Miedaner, R. Ciancanelli, W. W. Ellis, B. C. Noll, M. Rakowski DuBois, D. L. Dubois, Inorg. Chem. 2003, 42, 216-227;
58. b) R. M. Henry, R. K. Shoemaker, R. H. Newell, G. M. Jacobsen, D. L. DuBois, M. Rakowski DuBois, Organometallics 2005, 24, 2481-2491;
59. c) A. D. Wilson, R. H. Newell, M. J. McNevin, J. T. Muckerman, M. Rakowski DuBois, D. L. Dubois, J. Am. Chem. Soc. 2006, 128, 358-366;
60. d) R. M. Henry, R. K. Shoemaker, D. L. DuBois, M. Rakowski DuBois, J. Am. Chem. Soc. 2006, 128, 3002-3010;
61. e) A. D. Wilson, R. Shoemaker, A. Miedaner, M. Rakowski DuBois, D. L. Dubois, Proc. Natl. Acad. Sci. USA 2007, 104, 6951-6956;
62. f) K. Fraze, A. D. Wilson, A. M. Appel, M. Rakowski DuBois, D. L. Dubois, Organometallics 2007, 26, 3918-3924, and references therein.
63. a) L. Schwartz, G. Eilers, L. Eriksson, A. Gogoll, R. Lomoth, S. Ott, Chem. Commun. 2006, 520-522;
64. b) G. Eilers, L. Schwartz, M. Stein, G. Zampella, L. De Gioia, S. Ott, R. Lomoth, Chem. Eur. J. 2007, 13, 7075-7084.
65. F. Wang, M. Wang, X. Liu, K. Jin, W. Dong, L. Sun, Dalton Trans. 2007, 3812-3819.
66. a) U. Koelle, S. Ohst, Inorg. Chem. 1986, 25, 2689-2694;
67. b) U. Koelle, New J. Chem. 1992, 16, 157-169.
68. I. Bhugun, D. Lexa, J.-M. Savéant, J. Am. Chem. Soc. 1996, 118, 3982-3983.
69. D. A. Valyaev, M. G. Peterleitner, O. V. Semeikin, K. I. Utegenov, N. A. Ustynyuk, A. Sournia-Saquet, N. Lugan, G. Lavigne, J. Organomet. Chem. 2007, 692, 3207-3211.
70. J.-F. Capon, S. Ezzaher, F. Gloaguen, F. Y. Pétillon, P. Schollhammer, J. Talarmin, T. Davin, J. E. McGrady, K. W. Muir, New J. Chem. 2007, 31, 2052-2064.
71. S. J. Borg, T. Behrsing, S. P. Best, M. Razavet, X. Liu, C. J. Pickett, J. Am. Chem. Soc. 2004, 126, 16988-16999.
72. S. J. Borg, J. W. Tye, M. B. Hall, S. P. Best, Inorg. Chem. 2007, 46, 384-394.
73. a) M. H. Cheah, S. J. Borg, M. I. Blondin, S. P. Best, Inorg. Chem. 2004, 43, 5635-5644;
74. b) M. H. Cheah, S. J. Borg, S. P. Best, Inorg. Chem. 2001, 46, 1741-1750.
75. J. Windhager, M. Rudolph, S. Bräutigam, H. Görls, W. Weigand, Eur. J. Inorg. Chem. 2007, 2748-2760.
76. L.-C. Song, Z.-Y. Yang, Y.-J. Hua, U.-T. Wang, Y. Liu, Q.-M. Hu, Organometallics 2007, 26, 2106-2110.
77. 2: A. K. Justice, R. C. Linck, T. B. Rauchfuss, Inorg. Chem. 2006, 45, 2406-2412.
78. C. Greco, G. Zampella, L. Bertini, M. Bruschi, P. Fantucci, L. De Gioia, Inorg. Chem. 2007, 46, 108-116.
79. D. Chong, I. P. Georgakaki, R. Mejia-Rodriguez, J. Sanabria-Chinchilla, M. P. Soriaga, M. Y. Darensbourg, Dalton Trans. 2003, 4158-4163.
80. 2S)] are not detailed herein.
81. [42,43]
82. [44,45]
83. X. L. Hu, B. S. Brunschwig, J. C. Peters, J. Am. Chem. Soc. 2007, 129, 8988-8998.
84. K. Izutzu, Acid-Base Dissociation Constants in Dipolar Aprotic Solvents, IUPAC Chemical Data Series No. 35, Blackwell Scientific Publications. Oxford, 1990.
85. a) M. K. Chantooni, Jr., I. M. Kolthoff, J. Am. Chem. Soc. 1970, 92, 2236-2239;
86. b) I. M. Kolthoff, M. K. Chantooni, Jr., J. Am. Chem. Soc. 1968, 90, 3320-3326;
87. c) I. M. Kolthoff, S. Ikeda, J. Phys. Chem. 1961, 65, 1020-1026.
88. J. F. Coetzee, D. K. McGuire, J. Phys. Chem. 1963, 67, 1810-1814.
89. a(HOTs) = 8.0 in MeCN: T. Fujinaga, I. Sakamoto, J. Electroanal. Chem. 1977, 85, 185-201.
90. a(HOTs) = 8.6 in MeCN: I. Leito, I. Kaljurand, I. A. Koppel, L. M. Yagupolskii, V. M. Vlasov, J. Org. Chem. 1998, 63, 7868-7874.
91. -1] is the scan rate in CV experiments. An EC process comprises an electron-transfer step (E) followed by a chemical reaction (C).
92. The potential of the peak around -1.4 V shifts negatively upon addition of acid.
93. P. Das. J.-F. Capon, F. Gloaguen, F. Y. Pétillon, P. Schollhammer, J. Talarmin, Inorg. Chem. 2004, 43, 8203-8205.
94. a) A. J. Bard, L. R. Faulkner, Electrochemical Methods. Fundamentals and Applications, Wiley, New York, 1980, Chap. 11, pp. 429-485;
95. b) E. R. Brown, R. F. Large in Techniques of Chemistry, Vol. 1, Physical Methods of Chemistry, Part MA. (Ed.: A. Weissberger). Wiley, New York. 1971, Chap. 6, pp. 423-530.
96. J.-M. Savéant, Elements of Molecular and Biomolecular Electrochemistry - An Electrochemical Approach to Electron Transfer Chemistry, Wiley, New York, 2006, Chap. 2. pp. 78-181.
97. X. Zhao, Y.-M. Hsiao, J. H. Reibenspies, M. Y. Darensbourg, Inorg. Chem. 2002, 41, 699-708.
98. T. Liu, M. Wang, Z. Shi, H. Cui, W. Dong, J. Chen, B. Åkermark, L. Sun, Chem. Eur. J. 2004, 10, 4474-4479.
99. G. Si, L.-Z. Wu, W.-G. Wang, J. Ding, X.-F. Shan, Y.-P. Zhao, C.-H. Tung, M. Xu, Tetrahedron Lett. 2007, 48, 4775-4779.
100. a) C. Tard, PhD. Thesis, University of East Anglia, 2005;
101. b) C. J. Pickett, personal communication.
102. D. T. Pierce, W. E. Geiger, J. Am. Chem. Soc. 1992, 114, 6063-6073, and references therein.
103. For detailed information concerning DigiElch, see http://www.elch-soft. com and: a) M. Rudolph, J. Electroanal. Chem. 2003, 543, 23-29;
104. b) M. Rudolph, J. Electroanal. Chem. 2004, 571, 289-307;
105. c) M. Rudolph, J. Comput. Chem. 2005, 26, 619-632;
106. d) M. Rudolph, J. Comput. Chem. 2005, 26, 633-641;
107. e) M. Rudolph, J. Comput. Chem. 2005, 26, 1193-1204.
108. EH calculations were performed with the CACAO package developped by Mealli and Proserpio: C. Mealli, D. M. Proserpio, J. Chem. Educ 1990, 67, 399-402.
109. 4]/[1] > 3 (Figure 1).
110. 2 from 1-2H.
111. 4; Scheme 5).
112. J. W. Tye, M. Y. Darensbourg, M. B. Hall, Inorg. Chem. 2006, 45, 1552-1559.
113. A. K. Justice, G. Zampella, L. De Gioia, T. B. Rauchfuss, J. I. van der Vlugt, S. R. Wilson, Inorg. Chem. 2007, 46, 1655-1664.
114. S. Ezzaher, J.-F. Capon, F. Gloaguen, F. Y. Pétillon, P. Schollhammer, J. Talarmin, Inorg. Chem. 2001, 46, 9863-9872.
115. [23a] On the same grounds, metal-based reduction of the diiron complex in Scheme 9 is expected to result in an increased basicity of the metal site, which should be favourable to proton migration from the N atom to the iron centre.