Electronically unsaturated three-coordinate chloride and methyl complexes of iron, cobalt, and nickel

Journal of the American Chemical Society

Volumn 124, Issue 48, 2002, Pages 14416-14424

  Holland, Patrick L ^a   Cundari, Thomas R ^a,b,c   Perez, Lanyn L ^a   Eckert, Nathan A ^a   Lachicotte, Rene J ^a  

^a UNIVERSITY OF ROCHESTER   (United States)

^b University of Memphis   (United States)

^c UNIVERSITY OF NORTH TEXAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; COBALT; CRYSTALS; IRON; NICKEL;

LIGANDS;

ORGANOMETALLICS;

COBALT COMPLEX; IRON COMPLEX; NICKEL COMPLEX;

ARTICLE; CALCULATION; CHEMICAL BINDING; COMPLEX FORMATION; CRYSTAL STRUCTURE; ELECTRON MICROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; THERMOSTABILITY;

EID: 0037021483     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja025583m     Document Type: Article

References (87)

1. (a ) Cummins, C. C. Prog. Inorg. Chem. 1998, 47, 685-836.
2. (b) Alvarez, S. Coord. Chem. Rev. 1999, 193-195, 13-41.
3. (a) Power, P. P. Comments Inorg. Chem. 1989, 8, 177-202.
4. (b) Power, P. P. Chemtracts: Inorg. Chem. 1994, 6, 181-195.
5. (c) Ellison, J. J.; Ruhlandt-Senge, K.; Power, P. P. Angew. Chem., Int. Ed. Engl. 1994, 33, 1178-1180.
6. (d) Wehmschulte, R. J.; Power, P. P. Organometallics 1995, 14, 3264-3267.
7. (a) Murray, B. D.; Power, P. P. Inorg. Chem. 1984, 23, 4584-4588.
8. (b) Murray, B. D.; Power, P. P. J. Am. Chem. Soc. 1984, 106, 7011-7015.
9. (c) Hope, H.; Olmstead, M. M.; Murray, B. D.; Power, P. P. J. Am. Chem. Soc. 1985, 107, 712-713.
10. (d) Olmstead, M. M.; Power, P. P.; Sigel, G. Inorg. Chem. 1986, 25, 1027-1033.
11. (e) Ellison, J. J.; Power, P. P.; Shoner, S. C. J. Am. Chem. Soc. 1989, 111, 8044-8046.
12. (f) Bartlett, R. A.; Ellison, J. J.; Power, P. P.; Shoner, S. C. Inorg. Chem. 1991, 30, 2888-2894.
13. (g) Olmstead, M. M.; Power, P. P.; Shoner, S. C. Inorg. Chem. 1991, 30, 2547- 2551.
14. (h) Power, P. P.; Shoner, S. C. Angew. Chem., Int. Ed. Engl. 1991, 30, 330-332.
15. (i) Chen, H.; Olmstead, M. M.; Pestana, D. C.; Power, P. P. Inorg. Chem. 1991, 30, 1783-1787.
16. -: (a) MacDonnell, F. M.; Ruhlandt-Senge, K.; Ellison, J. J.; Holm, R. H.; Power, P. P. Inorg. Chem. 1995, 34, 1815-1822.
17. (b) Sanakis, Y.; Power, P. P.; Stubna, A.; Münck, E. Inorg. Chem. 2002, 41, 2690-2696.
18. (c) Agostic interactions in some low-coordinate iron thiolate complexes make higher coordinate descriptions more accurate: Evans, D. J.; Hughes, D. L.; Silver, J. Inorg. Chem. 1997, 36, 747-748.
19. Neithamer, D. R.; LaPointe, R. E.; Wheeler, R. A.; Richeson, D. S.; Van Duyne, G. D.; Wolczanski, P. T. J. Am. Chem. Soc. 1989, 111, 9056-9072.
20. (a) Cummins, C. C.; Baxter, S. M.; Wolczanski, P. T. J. Am. Chem. Soc. 1988,110, 8731-8733.
21. (b) Schafer, D. F.; Wolczanski, P. T. J. Am. Chem. Soc. 1998, 120, 4881-4882.
22. Cummins, C. C. Chem. Commun. 1998, 1777-1786 and references within.
23. (a) Odom, A. L.; Cummins, C. C.; Protasiewicz, J. D. J. Am. Chem. Soc. 1995, 117, 6613-6614.
24. (b) Veige, A. S.; Slaughter, L. M.; Wolczanski. P. T.; Matsunaga, N.; Decker, S. A.; Cundari, T. R. J. Am. Chem. Soc. 2001, 123, 6419-6420.
25. (a) There are short Fe-Fe contacts of 2.65 ± 0.04 Å in the FeMoco that probably modify the behavior of iron: Mayer, S. M.; Lawson, D. M.; Gormal, C. A.; Roe, S. M.; Smith, B. E. J. Mol. Biol. 1999, 292, 871-891.
26. (b) A very recent paper presents evidence that there is a fourth ligand coordinated to these iron atoms: Einsle, O.; Tezcan, F. A.; Andrade, S. L. A.; Schmid, B.; Yoshida, M.; Howard, J. B.; Rees, D. C. Science 2002, 297, 1696-1700.
27. 2 at Fe: (a) Lee, H.-I.; Sorlie, M.; Christiansen, J.; Song, R.; Dean, D. R.; Hales, B. J.; Hoffman, B. M. J. Am. Chem. Soc. 2000, 122, 5582-5587.
28. (b) Christiansen, J.; Dean, D. R.; Seefeldt, L. C. Annu. Rev. Plant Physiol. Plant Mol. Biol. 2001, 52, 269-295.
29. (c) Benton, P. M. C.; Mayer, S. M.; Shao, J.; Hoffman, B. M.; Dean, D. R.; Seefeldt, L. C. Biochemistry 2001, 40, 13816-13825.
30. (d) Krahn, E.; Weiss, B. J. R.; Kröckel, M.; Groppe, J.; Henkel, G.; Cramer, S. P.; Trautwein, A. X.; Schneider, K.; Müller, A. J. Biol. Inorg. Chem. 2002, 7, 37-45.
31. 2 binding to the FeMoco: (a) Dance, I. Chem. Commun. 1998, 523-530.
32. (b) Siegbahn, P. E. M.; Westerberg, J.; Svensson, M.; Crabtree, R. H. J. Phys. Chem. B 1998, 102, 1615- 1623.
33. (c) Rod, T. H.; Nørskov, J. K. J. Am. Chem. Soc. 2000, 122, 12751-12763.
34. Smith, J. M.; Lachicotte, R. J.; Pittard, K. A.; Cundari, T. R.; Lukat-Rodgers, G.; Rodgers, K. R.; Holland, P. L. J. Am. Chem. Soc. 2001, 123, 9222-9223.
35. Bourget-Merle, L.; Lappert, M. F.; Severn, J. R. Chem. Rev. 2002, 102, in press.
36. (a) Holland, P. L.; Tolman, W. B. J. Am. Chem. Soc. 1999, 121, 7270-7271.
37. (b) Holland, P. L.; Tolman, W. B. J. Am. Chem. Soc. 2000, 122, 6331-6332.
38. (c) Randall, D. W.; George, S. D.; Holland, P. L.; Hedman, B.; Hodgson, K. O.; Tolman, W. B.; Solomon, E. I. J. Am. Chem. Soc. 2000, 122, 11632-11648.
39. (d) Jazdzewski, B. A.; Holland, P. L.; Pink, M.; Young, V. G., Jr.; Spencer, D. J. E.; Tolman, W. B. Inorg. Chem. 2001, 40, 6097-6107.
40. (e) Spencer, D. J. E.; Aboelella, N. W.; Reynolds, A. M.; Holland, P. L.; Tolman, W. B. J. Am. Chem. Soc. 2002, 124, 2108-2109.
41. (a) Four-coordinate nickel complexes of the protonated diketimine ligand: Feldman, J.; McLain, S. J.; Parthasarathy, A.; Marshall, W. J.; Calabrese, J. C.; Arthur, S. D. Orgamometallics 1997, 16, 1514-1516.
42. (b) Power's group has recently created some three-coordinate cobalt and iron complexes using diketiminate ligands: Panda, A.; Stender, M.; Wright, R. J.; Olmstead, M. M.; Klavins, P.; Power, P. P. Inorg. Chem. 2002, 41, 3909-3916.
43. Smith, J. M.; Lachicotte, R. J.; Holland, P. L. Chem. Commun. 2001, 1542-1543.
44. Andres, H.; Bominaar, E.; Smith, J. M.; Eckert, N. A.; Holland, P. L.; Münck, E. J. Am. Chem. Soc. 2002, 124, 3012-3025.
45. 2H NMR spectra. See: Reuben, J.; Fiat, D. J. Am. Chem. Soc. 1969, 91, 1242. It is likely that the methyl protons/ deuterons are relaxed by the paramagnetic iron too quickly for observation.
46. (a) Radzewich, C. E.; Guzei, I. A.; Jordan, R. F. J. Am. Chem. Soc. 1999, 121, 8673-8674.
47. (b) Prust, J.; Stasch, A.; Zheng, W.; Roesky, H. W.; Alexopoulos, E.; Uson, I.; Boehler, D.; Schuchardt, T. Organometallics 2001, 20, 3825-3828.
48. 2 ≈ T.
49. Analysis of β-diketiminate distortion: (a) Stender, M.; Eichler, B. E.; Hardman, N. J.; Power, P. P.; Prust, J.; Noltemeyer, M.; Roesky, H. W. Inorg. Chem. 2001, 40, 2794-2799.
50. (b) Hitchcock, P. B.; Lappert, M. F.; Layh, M. J. Chem. Soc., Dalton Trans. 2001, 2409-2416.
51. (c) MacAdams, L.; Kim, W.-K.; Liable-Sands, L. M.; Guzei, I. A.; Rheingold, A. L.; Theopold, K. H. Organometallics 2002, 21, 952-960.
52. (d) Bailey, P. J.; Coxall, R. A.; Dick, C. M.; Fabre, S.; Parsons, S. Organometallics 2001, 20, 798-801.
53. (e) Cheng, M.; Moore, D. R.; Reczek, J. J.; Chamberlain, B. M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2001, 123, 8738-8749.
54. Poli, R. Chem. Rev. 1996, 96, 2135-2204.
55. Cambridge Structural Database and VISTA, October 2001 release. Allen, R. H.; Kennard, O. Chem. Design Automation News 1993, 8, 31-37. Histograms generated by VISTA are in the Supporting Information.
56. Balch, A. L.; Olmstead, M. M.; Safari, N.; St. Claire, T. N. Inorg. Chem. 1994, 33, 2815-2822.
57. (a) Plutino, M. R.; Scolaro, L. M.; Romeo, R.; Grassi, A. Inorg. Chem. 2000, 39, 2712-2720.
58. (b) Gandelman, M.; Vigalok, A.; Konstantinovski, L.; Milstein, D. J. Am. Chem. Soc. 2000, 122, 9848-9849.
59. (c) Kanzelberger, M.; Singh, B.; Czerw, M.; Krogh-Jespersen, K.; Goldman, A. S. J. Am. Chem. Soc. 2000, 122, 11017-11018.
60. (d) Crumpton, D. M.; Goldberg, K. I. J. Am. Chem. Soc. 2000, 122, 962-963.
61. (e) Fekl, U.; Goldberg, K. I. J. Am. Chem. Soc. 2002, 124, 6804-6805.
62. (f) Review: Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. Engl. 1998, 37, 2180-2192.
63. Recent evidence suggests that associative mechanisms without three-coordinate intermediates may be more reasonable in some cases: (a) Cao, Z.; Hall, M. B. Organometallics 2000, 19, 3338-3346. (b) Johansson, L.; Tilset, M. J. Am. Chem. Soc. 2001, 123, 739-740. (c) Zhong, H. A.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 2002, 124, 1378-1399. (d) Procelewska, J.; Zahl, A.; van Eldik, R.; Zhong, H. A.; Labinger, J. A.; Bercaw, J. E. Inorg. Chem. 2002, 41, 2808-2810.
64. Recent evidence suggests that associative mechanisms without three-coordinate intermediates may be more reasonable in some cases: (a) Cao, Z.; Hall, M. B. Organometallics 2000, 19, 3338-3346. (b) Johansson, L.; Tilset, M. J. Am. Chem. Soc. 2001, 123, 739-740. (c) Zhong, H. A.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 2002, 124, 1378-1399. (d) Procelewska, J.; Zahl, A.; van Eldik, R.; Zhong, H. A.; Labinger, J. A.; Bercaw, J. E. Inorg. Chem. 2002, 41, 2808-2810.
65. Recent evidence suggests that associative mechanisms without three-coordinate intermediates may be more reasonable in some cases: (a) Cao, Z.; Hall, M. B. Organometallics 2000, 19, 3338-3346. (b) Johansson, L.; Tilset, M. J. Am. Chem. Soc. 2001, 123, 739-740. (c) Zhong, H. A.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 2002, 124, 1378-1399. (d) Procelewska, J.; Zahl, A.; van Eldik, R.; Zhong, H. A.; Labinger, J. A.; Bercaw, J. E. Inorg. Chem. 2002, 41, 2808-2810.
66. Recent evidence suggests that associative mechanisms without three-coordinate intermediates may be more reasonable in some cases: (a) Cao, Z.; Hall, M. B. Organometallics 2000, 19, 3338-3346. (b) Johansson, L.; Tilset, M. J. Am. Chem. Soc. 2001, 123, 739-740. (c) Zhong, H. A.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 2002, 124, 1378-1399. (d) Procelewska, J.; Zahl, A.; van Eldik, R.; Zhong, H. A.; Labinger, J. A.; Bercaw, J. E. Inorg. Chem. 2002, 41, 2808-2810.
67. Kisko, J. L.; Hascall, T.; Parkin, G. J. Am. Chem. Soc. 1998, 120, 10561-10562.
68. Schehler, P. J.; Mandimutsira, B. S.; Riordan, C. G.; Liable-Sands, L. M.; Incarvito, C. D.; Rheingold, A. L. J. Am. Chem. Soc. 2001, 123, 331-332.
69. Jewson, J. D.; Liable-Sands, L. M.; Yap, G. P. A.; Rheingold, A. L.; Theopold, K. H. Organometallics 1999, 18, 300-305.
70. (a) Lindahl, P. A. Biochemistry 2002, 41. 2097-2105.
71. (b) Seravalli, J.; Kumar, M.; Ragsdale, S. W. Biochemistry 2002, 41, 1807-1819.
72. (a) Ermler, U.; Grabarse, W.; Shima, S.; Goubeaud, M.; Thauer, R. K. Science 1997, 278, 1457-1462.
73. (b) Homg, Y.-C.; Beeker, D. F.; Ragsdale, S. W. Biochemistry 2001, 40, 12875-12885.
74. Pelmenschikov, V.; Blomberg, M. R. A.; Siegbahn, P. E. M.; Crabtree, R. H. J. Am. Chem. Soc. 2002, 124, 4039-4049.
75. (a) Jolly, P. W.; Jonas, K.; Krueger, C.; Tsay, Y. H. J. Organomet. Chem. 1971, 33, 109-122.
76. (b) D'Aniello, M. J.; Barefield, E. K. J. Am. Chem. Soc. 1976, 98, 1610-1611.
77. Diamagnetic square-planar complexes of nickel(II) are common.
78. A recent example: Shultz, C. S.; DeSimone, J. M.; Brookhart, M. J. Am. Chem. Soc. 2001, 123, 9172-9173.
79. Smith, I. M.; Lachicotte, R. L.; Holland, P. L. Organometallics 2002, 21. 4808-4814.
80. 1 from an inversion-recovery experiment is described: Levy, G. C.; Peat, I. R. J. Magn. Reson. 1975, 18, 500-521.
81. Schubert. E. M. J. Chem. Educ. 1992, 69, 62.
82. Pray, A. R. Inorg. Synth. 1990, 28, 321-323.
83. Kern, R. J. J. Inorg. Nucl. Chem. 1962, 24, 1105-1109,
84. Eckert, N. A.; Bones, E. M.; Lachicotte, R. L.; Holland, P., L., submitted.
85. Budzelaar, P. H. M.; van Oort, A. B.; Orpen, A. G. Eur. J. Inorg. Chem. 1998, 1485-1494.
86. Holland, P. L.; Smith, M. E.; Andersen, R, A.; Bergman, R. G. J. Am. Chem. Soc. 1997, 119, 12815-12823.
87. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A. Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q., Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz,J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I., Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. GAUSSIAN: Gaussian, Inc.: Pittsburgh, PA, 1998.