Reactions of the terminal NiII-OH group in substitution and electrophilic reactions with carbon dioxide and other substrates: Structural definition of binding modes in an intramolecular NiIIFeII bridged site

Journal of the American Chemical Society

Volumn 132, Issue 13, 2010, Pages 4693-4701

  Huang, Deguang ^a   Holm, R H ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING MODES; BIOMIMETIC CHEMISTRY; CARBON MONOXIDE DEHYDROGENASE; CLUSTER STRUCTURE; COMPLEX 1; CYANIDE COMPLEXES; ELECTROPHILIC REACTION; ETHYL FORMATE; MACROCYCLES; MACROCYLES; OH GROUP; PINCER LIGANDS; REVERSIBLE REACTION; UNIDENTATE;

BINDING ENERGY; BIOMIMETICS; CARBON DIOXIDE; CARBON MONOXIDE; CYANIDES; SUBSTRATES;

SYNTHESIS (CHEMICAL);

BICARBONATE; CARBON DIOXIDE; CARBON MONOXIDE DEHYDROGENASE; CYANIDE; FORMIC ACID; HYDROXIDE; IRON; MACROCYCLIC COMPOUND; NICKEL; SULFUR; WATER;

ARTICLE; BIOMIMETICS; CLUSTER ANALYSIS; COMPLEX FORMATION; REACTION ANALYSIS; SEPARATION TECHNIQUE; SUBSTITUTION REACTION; SYNTHESIS;

ALDEHYDE OXIDOREDUCTASES; BINDING SITES; CARBON DIOXIDE; CATALYSIS; HYDROXYL RADICAL; IRON; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MULTIENZYME COMPLEXES; NICKEL; ORGANOMETALLIC COMPOUNDS; SULFIDES;

EID: 77950790801     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja1003125     Document Type: Article

References (51)

1. Groysman, S. and Holm, R. H. Biochemistry 2009, 48, 2310 - 2320
2. Abbreviations are given in Chart 1.
3. Ragsdale, S. W. and Kumar, M. Chem. Rev. 1996, 96, 2515 - 2539
4. Ragsdale, S. W. Crit. Rev. Biochem. Mol. Biol. 2004, 39, 165 - 195
5. Lindahl, P. A. Biochemistry 2002, 41, 2097 - 2105
6. Lindahl, P. A. and Graham, D. E. Metal Ions Life Sci. 2007, 2, 357 - 415
7. Drennan, C. L., Doukov, T. I., and Ragsdale, S. W. J. Biol. Inorg. Chem. 2004, 9, 511 - 515
8. Dobbek, H., Svetlitchnyi, V., Liss, J., and Meyer, O. J. Am. Chem. Soc. 2004, 126, 5382 - 5387
9. Volbeda, A. and Fontecilla-Camps, J. C. J. Chem. Soc., Dalton Trans. 2005, 3443 - 3450
10. Jeoung, J.-H. and Dobbek, H. Science 2007, 318, 1461 - 1464
11. Gong, W., Hao, B., Wei, Z., Ferguson, D. J., Tallant, T., Krzycki, J. A., and Chan, M. K. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 9558 - 9563
12. Kung, Y., Doukov, T. I., Seravalli, J., Ragsdale, S. W., and Drennan, C. L. Biochemistry 2009, 48, 7432 - 7440
13. Ciurli, S., Ross, P. K., Scott, M. J., Yu, S.-B., and Holm, R. H. J. Am. Chem. Soc. 1992, 114, 5415 - 5423
14. Zhou, J., Scott, M. J., Hu, Z., Peng, G., Münck, E., and Holm, R. H. J. Am. Chem. Soc. 1992, 114, 10843 - 10854
15. Zhou, J., Raebiger, J. W., Crawford, C. A., and Holm, R. H. J. Am. Chem. Soc. 1997, 119, 6242 - 6250
16. Panda, R., Berlinguette, C. P., Zhang, Y., and Holm, R. H. J. Am. Chem. Soc. 2005, 127, 11092 - 11101
17. Sun, J., Tessier, C., and Holm, R. H. Inorg. Chem. 2007, 46, 2691 - 2699
18. Hikichi, S., Ogihara, T., Fujisawa, K., Kitajima, N., Akita, M., and Moro-oka, Y. Inorg. Chem. 1997, 36, 4539 - 4547
19. MacBeth, C. E., Hammes, B. S., Young, V. G., Jr., and Borovik, A. S. Inorg. Chem. 2001, 40, 4733 - 4741
20. Bénisvy, L., Halut, S., Donnadieu, B., Tuchagues, J.-P., Chottard, J.-C., and Li, Y. Inorg. Chem. 2006, 45, 2403 - 2405
21. Bennett, M. A., Jin, H., and Willis, A. C. J. Organomet. Chem. 1993, 451, 249 - 256
22. Cámpora, J., Palma, P., del Rio, D., and Álvarez, E. Organometallics 2004, 23, 1652 - 1655
23. Johansson, R. and Wendt, O. F. Organometallics 2007, 26, 2426 - 2430
24. Britovsek, G. J. P., England, J., and White, A. J. P. Inorg. Chem. 2005, 44, 8125 - 8134
25. Wendt, O. F., Kaiser, N.-F. K., and Elding, L. I. J. Chem. Soc., Dalton Trans. 1997, 4733 - 4737
26. Sheldrick, G. M. Acta Crystallogr. 2009, A64, 112 - 122
27. See the paragraph at the end of this article for Supporting Information available.
28. Patra, A. K. and Mukherjee, R. Inorg. Chem. 1999, 38, 1388 - 1393
29. Wasilke, J.-C., Wu, G., Bu, X., Kehr, G., and Erker, G. Organometallics 2005, 24, 4289 - 4297
30. Carmona, E., Marín, J. M., Palma, P., Paneque, M., and Poveda, M. L. Inorg. Chem. 1989, 28, 1895 - 1900
31. Kitajima, N., Hikuchi, S., Tanaka, M., and Moro-oka, Y. J. Am. Chem. Soc. 1993, 115, 5496 - 5508
32. Barrios, A. M. and Lippard, S. J. J. Am. Chem. Soc. 2000, 122, 9172 - 9177
33. Kersting, B. Angew. Chem., Int. Ed. 2001, 40, 3988 - 3990
34. Orlandini, A. and Sacconi, L. Inorg. Chem. 1976, 15, 78 - 85
35. Meyer, F., Kaifer, E., Kircher, P., Heinze, K., and Pritzkow, H. Chem. - Eur. J. 1999, 5, 1617 - 1630
36. Cámpora, J., Matas, I., Palma, P., Graiff, C., and Tiripicchio, A. Organometallics 2005, 24, 2827 - 2830
37. Kieber-Emmons, M. T., Schenker, R., Yap, G. P. A., Brunold, T. C., and Riordan, C. G. Angew. Chem., Int. Ed. 2004, 43, 6716 - 6718
38. López, G., Garcia, G., Sánchez, G., Garcia, J., and Vicente, C. J. Chem. Soc., Chem. Commun. 1989, 1045 - 1046
39. Gavrilova, A. L. and Bosnich, B. Chem. Rev. 2004, 104, 349 - 383
40. Vigato, P. A., Tamburini, S., and Bertolo, L. Coord. Chem. Rev. 2007, 251, 1311 - 1492
41. Mahoney, J. M., Nawaratna, G. U., Beatty, A. M., Duggan, P. J., and Smith, B. D. Inorg. Chem. 2004, 43, 5902 - 5907
42. Mahoney, J. M., Stucker, K. A., Jiang, H., Carmichael, I., Brinkmann, N. R., Beatty, A. M., Noll, B. C., and Smith, B. D. J. Am. Chem. Soc. 2005, 127, 2922 - 2928
43. Addison, A. W., Nageswara Rao, T., Reedijk, J., van Rijn, J., and Verschoor, G. C. J. Chem. Soc., Dalton Trans. 1984, 1349 - 1356
44. Huang, D., Deng, L., Sun, J., and Holm, R. H. Inorg. Chem. 2009, 48, 6159 - 6166
45. Scott, M. J., Zhang, H. H., Lee, S. C., Hedman, B., Hodgson, K. O., and Holm, R. H. J. Am. Chem. Soc. 1995, 117, 568 - 569
46. Scott, M. J., Goddard, C. A., and Holm, R. H. Inorg. Chem. 1996, 35, 2558 - 2567
47. Scott, M. J. and Holm, R. H. J. Am. Chem. Soc. 1994, 116, 11357 - 11367
48. Lim, B. S. and Holm, R. H. Inorg. Chem. 1998, 37, 4898 - 4908
49. Lozano, A. A., Sáez, M., Pérez, J., García, L., Lezama, L., Rojo, T., López, G., García, G., and Santana, M. D. Dalton Trans. 2006, 3906 - 3911
50. Morales-Morales, D. In Modern Carbonylation Methods; Kollár, L., Ed.; Wiley-VCH: Weinheim, 2008; pp 27 - 64.
51. While reaction of CO with reduced Ni complexes remains a possibility, preliminary investigation of 1 (DMF) and 7 (acetonitrile) by cyclic voltammetry reveals only quasi-reversible reductions at -1.40 and -1.31 V, respectively, vs SCE. Both complexes showed reversible oxidations (1, +0.67 V; 7, +1.04 V).