Nitrosyl derivatives of diiron(I) dithiolates mimic the structure and lewis acidity of the [FeFe]-hydrogenase active site

Journal of the American Chemical Society

Volumn 130, Issue 36, 2008, Pages 12021-12030

  Olsen, Matthew T ^a   Bruschi, Maurizio ^b   De Gioia, Luca ^b   Rauchfuss, Thomas B ^a   Wilson, Scott R ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^b UNIVERSITY OF MILANO BICOCCA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

DITHIOLATES; ELECTRONIC ASYMMETRY; HYDROGENASE ACTIVE SITE; LEWIS ACIDITY;

DERIVATIVES;

CARBONYL DERIVATIVE; IRON HYDROGENASE; LEWIS ACID; PHOSPHINE DERIVATIVE; THIOL DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CRYSTALLOGRAPHY; DENSITY FUNCTIONAL THEORY; ENZYME ACTIVE SITE; NITROSYLATION; SPECTROSCOPY; STRUCTURE ANALYSIS;

BINDING SITES; BIOMIMETIC MATERIALS; CRYSTALLOGRAPHY, X-RAY; ELECTROCHEMISTRY; FERRIC COMPOUNDS; HYDROGENASE; IRON-SULFUR PROTEINS; MODELS, MOLECULAR; NITROGEN OXIDES; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; SULFHYDRYL COMPOUNDS;

EID: 51749103530     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja802268p     Document Type: Article

References (79)

1. De Lacey, A. L.; Fernández, V. M.; Rousset, M.; Cammack, R. Chem. Rev. 2007, 107, 4304-4330.
2. (a) Fontecilla-Camps, J. C.; Volbeda, A.; Cavazza, C.; Nicolet, Y. Chem. Rev. 2007, 107, 4273-4303.
3. (b) Vignais, P. M.; Billoud, B. Chem. Rev. 2007, 107, 4206-4272.
4. Liu, X.; Ibrahim, S. K.; Tard, C.; Pickett, C. J. Coord. Chem. Rev. 2005, 249, 1641-1652.
5. Hogarth, G. In Comprehensive Organometallic Chemistry III; Crabtree, R., Mingos, M., Eds.; Elsevier: Amsterdam, 2007.
6. Justice, A. K.; Zampella, G.; De Gioia, L.; Rauchfuss, T. B. Chem. Commun. 2007, 2019-2021.
7. (a) Nicolet, Y.; Lemon, B. J.; Fontecilla-Camps, J. C.; Peters, J. W. Trends Biochem. Sci. 2000, 25, 138-143.
8. (b) Pandey, A. S.; Harris, T. V.; Giles, L. J.; Peters, J. W.; Szilagyi, R. K. J. Am. Chem. Soc. 2008, 130, 4533-4540.
9. Justice, A. K.; Rauchfuss, T. B.; Wilson, S. R. Angew. Chem., Int. Ed. 2007, 46, 6152-6154.
10. Liu, T.; Darensbourg, M. Y. J. Am. Chem. Soc. 2007, 129, 7008-7009.
11. van der Vlugt, J. I.; Rauchfuss, T. B.; Whaley, C. M.; Wilson, S. R. J. Am. Chem. Soc. 2005, 127, 16012-16013.
12. Arabi, M. S.; Mathieu, R.; Poilblanc, R. J. Organomet. Chem. 1979, 177, 199-209.
13. de Beer, J. A.; Haines, R. J. J. Organomet. Chem. 1972, 36, 297-312.
14. Song, L.-C.; Yang, Z.-Y.; Bian, H.-Z.; Hu, Q.-M. Organometallics 2004, 23, 3082-3084.
15. Tard, C.; Liu, X.; Ibrahim, S. K.; Bruschi, M.; De Gioia, L.; Davies, S. C.; Yang, X.; Wang, L.-S.; Sawers, G.; Pickett, C. J. Nature 2005, 433, 610-614.
16. (a) Nehring, J. L.; Heinekey, D. M. Inorg. Chem. 2003, 42, 4288-4292.
17. (b) Boyke, C. A.; Rauchfuss, T. B.; Wilson, S. R.; Rohmer, M.-M.; Bénard, M. J. Am. Chem. Soc. 2004, 126, 15151-15160.
18. (a) Capon, J.-F.; El Hassnaoui, S.; Gloaguen, F.; Schollhammer, P.; Talarmin, J. Organometallics 2005, 24, 2020-2022.
19. (b) Tye, J. W.; Lee, J.; Wang, H. W.; Mejia-Rodriguez, R.; Reibenspies, J. H.; Hall, M. B.; Darensbourg, M. Y. Inorg. Chem. 2005, 44, 5550-5552.
20. Lawrence, J. D.; Li, H.; Rauchfuss, T. B. Chem. Commun. 2001, 1482-1483.
21. (a) Arabi, M. S.; Mathieu, R.; Poilblanc, R. Inorg. Chim. Acta 1977, 23, L17-L18.
22. (b) Arabi, M. S.; Mathieu, R.; Poilblanc, R. Inorg. Chim. Acta 1979, 34, L207-L208.
23. (c) Bonnet, J. J.; Mathieu, R.; Poilblanc, R.; Ibers, J. A. J. Am. Chem. Soc. 1979, 101, 7487-7496.
24. (a) Mitoraj, M.; Michalak, A. Organometallics 2007, 26, 6576-6580.
25. (b) Richter-Addo, G. B.; Legzdins, P. Metal Nitrosyls; Oxford University Press: New York, 1992.
26. (c) Wu, C.-Y.; Chen, L.-H.; Hwang, W.-S.; Chen, H.-S.; Hung, C.-H. J. Organomet. Chem. 2004, 689, 2192-2200.
27. (a) Butler, A. R.; Megson, I. L. Chem. Rev. 2002, 102, 1155-1165.
28. (b) Wasser, I. M.; de Vries, S.; Moënne-Loccoz, P.; Schröder, I.; Karlin, K. D. Chem. Rev. 2002, 102, 1201-1234.
29. (c) Tsai, M.-L.; Liaw, W.-F. Inorg. Chem. 2006, 45, 6583-6585.
30. (d) Conradie, J.; Quarless, D. A., Jr.; Hsu, H.-F.; Harrop, T. C.; Lippard, S. J.; Koch, S. A.; Ghosh, A. J. Am. Chem. Soc. 2007, 129, 10446-10456.
31. (e) Harrop, T. C.; Song, D.; Lippard, S. J. J. Am. Chem. Soc. 2006, 128, 3528-3529.
32. (f) Harrop, T. C.; Song, D.; Lippard, S. J. J. Inorg. Biochem. 2007, 101, 1730-1738.
33. (a) Rauchfuss, T. B.; Weatherill, T. D. Inorg. Chem. 1982, 21, 827-831.
34. (b) Conrado, C. L.; Bourassa, J. L.; Egler, C.; Wecksler, S.; Ford, P. C. Inorg. Chem. 2003, 42, 2288-2293.
35. (a) Chen, H.-W.; Lin, C.-W.; Chen, C.-C.; Yang, L.-B.; Chiang, M.-H.; Liaw, W.-F. Inorg. Chem. 2005, 44, 3226-3232.
36. (b) Lee, C.-M.; Chen, C.-H.; Chen, H.-W.; Hsu, J.-L.; Lee, G.-H.; Liaw, W.-F. Inorg. Chem. 2005, 44, 6670-6679.
37. Adam, F. I.; Hogarth, G.; Richards, I.; Sanchez, B. E. Dalton Trans. 2007, 2495-2498.
38. Zhao, X.; Georgakaki, I. P.; Miller, M. L.; Yarbrough, J. C.; Darensbourg, M. Y. J. Am. Chem. Soc. 2001, 123, 9710-9711.
39. Duan, L. L.; Wang, M.; Li, P.; Na, Y.; Wang, N.; Sun, L. C. Dalton Trans. 2007, 1277-1283.
40. Justice, A. K.; Zampella, G.; De Gioia, L.; Rauchfuss, T. B.; van der Vlugt, J. I.; Wilson, S. R. Inorg. Chem. 2007, 46, 1655-1664.
41. Crabtree, R. H.; Lavin, M. Inorg Chem. 1986, 25, 805-812.
42. Lyon, E. J.; Georgakaki, I. P.; Reibenspies, J. H.; Darensbourg, M. Y. Angew. Chem., Int. Ed. 1999, 38, 3178-3180.
43. Li, P.; Wang, M.; He, C.; Li, G.; Liu, X.; Chen, C.; Åkermark, B.; Sun, L. Eur. J. Inorg. Chem. 2005, 2506-2513.
44. Hogarth, G.; Richards, I. Inorg. Chem. Commun. 2007, 10, 66-70.
45. Georgakaki, I. P.; Thomson, L. M.; Lyon, E. J.; Hall, M. B.; Darensbourg, M. Y. Coord. Chem. Rev. 2003, 238-239, 255-266.
46. Justice, A. K.; Nilges, M. J.; Rauchfuss, T. B.; Wilson, S. R.; De Gioia, L.; Zampella, G. J. Am. Chem. Soc. 2008, 130, 5293-5301.
47. Thomas, C. M.; Liu, T.; Hall, M. B.; Darensbourg, M. Y. Chem. Commun. 2008, 1563-1565.
48. (a) Sellmann, D.; Blum, N.; Heinemann, F. W.; Hess, B. A. Chem. - Eur. J. 2001, 7, 1874-1880.
49. (b) Serres, R. G.; Grapperhaus, C. A.; Bothe, E.; Bill, E.; Weyhermuller, T.; Neese, F.; Wieghardt, K. J. Am. Chem. Soc. 2004, 126, 5138-5153.
50. Justice, A. K.; De Gioia, L.; Nilges, M. J.; Rauchfuss, T. B.; Wilson, S. R.; Zampella, G. Inorg. Chem. [Online early access]. DOI: 10.1021/ic8007552. Published Online: July 12, 2008.
51. (a) Felton, G. A. N.; Vannucci, A. K.; Chen, J.; Lockett, L. T.; Okumura, N.; Petro, B. J.; Zakai, U. I.; Evans, D. H.; Glass, R. S.; Lichtenberger, D. L. J. Am. Chem. Soc. 2007, 129, 12521-12530.
52. (b) Borg, S. J.; Behrsing, T.; Best, S. P.; Razavet, M.; Liu, X.; Pickett, C. J. J. Am. Chem. Soc. 2004, 126, 16988-16999.
53. (c) Borg, S. J.; Tye, J. W.; Hall, M. B.; Best, S. P. Inorg. Chem. 2007, 46, 384-394.
54. Gloaguen, F.; Lawrence, J. D.; Rauchfuss, T. B.; Bénard, M.; Rohmer, M.-M. Inorg. Chem. 2002, 41, 6573-6582.
55. Mejia-Rodriguez, R.; Chong, D.; Reibenspies, J. H.; Soriaga, M. P.; Darensbourg, M. Y. J. Am. Chem. Soc. 2004, 126, 12004-12014.
56. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899-926.
57. Wang, H.; Xie, Y.; King, R. B.; Schaefer, H. F., III Inorg. Chem. 2008, 46, 1836-1847.
58. (a) Zhao, X.; Georgakaki, I. P.; Miller, M. L.; Mejia-Rodriguez, R.; Chiang, C.-Y.; Darensbourg, M. Y. Inorg. Chem. 2002, 41, 3917-3928.
59. (b) Fauvel, K.; Mathieu, R.; Poilblanc, R. Inorg. Chem. 1976, 15, 976-978.
60. Dahl, L. F.; Wei, C. H. Inorg. Chem. 1963, 2, 328-333.
61. Winter, A.; Zsolnai, L.; Huttner, G. Z. Naturforsch. 1982, 37b, 1430-1436.
62. Nicolet, Y.; Piras, C.; Legrand, P.; Hatchikian, C. E.; Fontecilla-Camps, J. C. Structure 1999, 7, 13-23.
63. Silakov, A.; Reijerse, E. J.; Albracht, S. P. J.; Hatchikian, E. C.; Lubitz, W. J. Am. Chem. Soc. 2007, 129, 11447-11458.
64. Peters, J. W.; Lanzilotta, W. N.; Lemon, B. J.; Seefeldt, L. C. Science 1998, 282, 1853-1858.
65. Paul, P. P.; Tyeklar, Z.; Farooq, A.; Karlin, K. D.; Liu, S.; Zubieta, J. J. Am. Chem. Soc. 1990, 112, 2430-2432.
66. Hayton, T. W.; Legzdins, P.; Sharp, W. B. Chem. Rev. 2002, 102, 935-991.
67. Cheah, M. H.; Borg, S. J.; Best, S. P. Inorg. Chem. 2007, 46, 1741-1750.
68. Gloaguen, F.; Lawrence, J. D.; Rauchfuss, T. B. J. Am. Chem. Soc. 2001, 123, 9476-9477.
69. (a) Adams, R. D.; Cotton, F. A.; Cullen, W. R.; Hunter, D. L.; Mihichuk, L. Inorg. Chem. 1975, 14, 1395-1399.
70. (b) Lyon, E. J.; Georgakaki, I. P.; Reibenspies, J. H.; Darensbourg, M. Y. J. Am. Chem. Soc. 2001, 123, 3268-3278.
71. Mocella, M. T.; Okamoto, M. S.; Barefield, E. K. Synth. React. Inorg. Met.-Org. Chem. 1974, 4, 69-90.
72. Nelson, J. H. Nuclear Magnetic Resonance Spectroscopy; Prentice Hall: New York, 2003.
73. (a) Becke, A. D. Phys. Rev. A 1986, 38, 3098-3100.
74. (b) Perdew, J. P. Phys. Rev. B 1986, 33, 8822-8824.
75. Schaefer, A.; Huber, C.; Ahlrichs, R. J. Chem. Phys. 1994, 100, 5829-5835.
76. (a) Niu, S.; Hall, M. B. Chem. Rev 2000, 100, 353-406.
77. (b) Bruschi, M.; Zampella, G.; Fantucci, P.; De Gioia, L. Coord. Chem. Rev. 2005, 249, 1620-1640.
78. (c) Siegbahn, P. E. M.; Tye, J. W.; Hall, M. B. Chem. Rev. 2007, 107, 4414-4435.
79. Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735-746.