Electronic structure of an iron-porphyrin-nitrene complex

Inorganic Chemistry

Volumn 49, Issue 1, 2010, Pages 243-248

  Conradie, Jeanet ^a,b   Ghosh, Abhik ^a  

^a UNIVERSITY OF TROMSØ   (Norway)

^b UNIVERSITY OF THE FREE STATE   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 73349085952     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic901897w     Document Type: Article

References (56)

1. Wigley, D. E. Prog. Inorg. Chem. 1994, 42, 239-482.
2. (a) Mayer, J. M. Comments Inorg. Chem. 1988, 8, 125-135.
3. (b) Nugent, W. A.; Mayer, J. M. Metal-Ligand Multiple Bonds; Wiley: New York, 1998.
4. (a) Dai, X.; Kapoor, P.; Warren, T. H. J. Am. Chem. Soc. 2004, 126, 4798.
5. (b) Kogut, E.; Wiencko, H. L.; Zhang, L.; Cordeau, D. E.; Warren, T. H. J. Am. Chem. Soc. 2005, 127, 11248.
6. (c) Shay, D. T; Yap, G. P. A.; Zakharov, L. N.; Rheingold, A. L.; Theopold, K. H. Angew. Chem., Int. Ed. 2005, 44, 1508-1510.
7. (d) Eckart, N. A.; Vaddadi, S.; Stoian, S.; Lachicotte, R. J.; Cundari, T. R.; Holland, P. L. Angew. Chem., Int. Ed. 2006, 45, 6868-6871.
8. Conradie, J.; Ghosh, A. J. Chem. Theory Comput. 2007, 3, 689-702.
9. (a) Brown, S. D.; Betley, T. A.; Peters, J. C. J. Am. Chem. Soc. 2003, 125, 322-323.
10. (b) Brown, S. D.; Peters, J. C. J. Am. Chem. Soc. 2005, 127, 1913-1923.
11. (c) Thomas, C. M.; Mankad, N. P.; Peters, J. C. J. Am. Chem. Soc. 2006, 128, 4956-4957.
12. (d) Shan, X. P.; Que, L., Jr. J. Inorg. Biochem. 2006, 100, 421433.
13. (e) Cowley, R. E.; Bontchev, R. P.; Sorrell, J.; Sarracino, O.; Feng, Y.; Wang, H.; Smith, J. M. J. Am. Chem. Soc. 2007, 129, 2424-2425.
14. (a) Tangen, E.; Conradie, J.; Ghosh, A. J. Chem. Theory Comput. 2007, 3, 448-457.
15. (b) Wasbotten, I. H.; Ghosh, A. Inorg. Chem. 2007, 46, 7890-7898.
16. Bart, S. C.; Lobkovsky, E.; Bill, E.; Chirik, P. J. J. Am. Chem. Soc. 2006, 128, 5302-5303.
17. Conradie, J.; Ghosh, A. J. Chem. Theory Comput. 2008, 4, 1576-1584.
18. Mehn, M. P.; Peters, J. C. J. Inorg. Biochem. 2006, 100, 634-643.
19. Berry, J. F. Comments Inorg. Chem. 20092C 30, 28-66.
20. Iron-imido species, however, have been postulated as reactive intermediates in certain metabolic pathways of cytochrome P450: (a) Hines, R. N.; Prough, R. A. J. Pharmacol. Exp. Ther. 1980, 214, 80-86.
21. (b) Prough, R. A; Freeman, P. C.; Hines, R. N. J. Biol. Chem. 1981, 256, 4178-4184.
22. (c) Breslow, R.; Gellman, S. H. J. Chem. Soc., Chem. Commun. 1982, 1400-1401.
23. (d) White, R. E.; McCarthy, M. B. J. Am. Chem. Soc. 1984, 106, 4922&-4926.
24. (e) Svastis, E. W.; Dawson, J. H.; Breslow, R.; Gellman, S. H. J. Am. Chem. Soc. 1985, 107, 6427-6428.
25. (a) Groves, J. T. J. Inorg. Biochem. 2006, 100, 434-447.
26. (b) Shan, X. P.; Que, L. J. Inorg. Biochem. 2006, 100, 421-433.
27. (c) Temer, J.; Palaniappan, V.; Gold, A.; Weiss, R.; Fitzgerald, M. M.; Sullivan, A. M.; Hosten, C. M. J. Inorg. Biochem. 2006, 100, 480-501.
28. Mahy, J. P.; Battioni, P.; Mansuy, D.; Fisher, J.; Weiss, J.; Mispelter, J.; Morgenstern-Badarau, I.; Gans, P. J. Am. Chem. Soc. 1984, 106, 1699-1706.
29. Mansuy, D.; Battioni, P.; Mahy, J. P. J. Am. Chem. Soc. 1982, 104, 4487-4489.
30. Klinker, E. K.; Jackson, T. A.; Jensen, M. P.; Stubna, A.; Juhász, G.; Bominaar, E. L.; Münck, E.; Que, L., Jr. Angew. Chem., Int. Ed. 2006, 118, 7554-7557.
31. We use the somewhat cumbersome term non-low-coordinate to refer to coordination numbers higher than 4. In effect, the term refers to squarepyramidal and octahedral geometries.
32. For a recent DFT study of iron-poprhyrin-mediated nitrene transfer, see: Moreau, Y.; Chen, H.; Derat, E.; Hirao, H.; Bolm, C.; Shaik, S. J. Phys. Chem. B 2007, 111, 10288-10299.
33. For reviews on transition-metal-mediated nitrene transfer, see: (a) Cenin, S.; Gallo, E.; Caselli, A.; Ragaini, F.; Fantauzzi, S.; Piangiolino, C. Coord. Chem. Rev. 2006, 250, 1234-1253.
34. (b) Fantauzzi, S.; Caselli, A.; Gallo, E. Dalton Trans. 2009, 5434-5443.
35. Mahy, J. P.; Battioni, P.; Mansuy, D. J. Am. Chem. Soc. 1986, 108, 1079-1080.
36. Mahy, J. P.; Battioni, P.; Bedi, G.; Mansuy, D.; Fischer, J.; Weiss, R.; Morgenstern-Badarau, I. Inorg. Chem. 1988, 27, 353-359.
37. Che, C. M.; Ho, C. M.; Huang, J. S. Coord. Chem. Rev. 2007, 251, 2145-2166.
38. Simonneaux, G; Le Maux, P. Top. Organomet. Chem. 2006, 17, 83-122.
39. Ghosh, A; Taylor, P. R. Curr. Opin. Chem. Biol. 2003, 7, 113-124.
40. Ghosh, A. J. Biol. Inorg. Chem. 2006, 11, 712-724.
41. (a) Ghosh, A.; Persson, B. J.; Taylor, P. R. Biol. Inorg. Chem. 2003, 8, 507-511.
42. (b)Conradie, J.;Ghosh, A. J.Phys. Chem. B 2007, 111, 12621-12624.
43. (c) Ghosh, A.; Gonzalez, E.; Tangen, E.; Roos, B. O. J. Phys. Chem. A 2008, 112, 12792-12798.
44. (d) Swart, M. J. Chem. Theory Comput. 2008, 4, 2057-2066.
45. (e) Jensen, K. P.; Cirera, J. J. Phys. Chem. A 2009, 113, 10033-10039.
46. The OPTX exchange functional: Handy, N. C.; Cohen, A. J. Mol. Phys. 2001, 99, 403-412.
47. The LYP correlation functional: Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
48. Velde, G. T.; Bickelhaupt, F. M.; Baerends, E. J.; Guerra, C. F.; Van Gisbergen, S. J. A.; Snijders, J. G.; Ziegler, T. J. Comput. Chem. 2001, 22, 2001.
49. (a) Perdew, J. P.; Chevary, J. A.; Vosko, S. H.; Jackson, K. A.; Perderson, M. R.; Singh, D. J.; Fiolhais, C. Phys. Rev. B1992, 46, 6671-6687.
50. (b) Erratum: Perdew, J. P.; Chevary, J. A.; Vosko, S. H.; Jackson, K. A.; Perderson, M. R.; Singh, D. J.; Fiolhais, C. Phys. Rev. B 1993, 48, 4978.
51. Stephens, J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627.
52. Reiher, M.; Salomon, O.; Hess, B. A. Theor. Chem. Acc. 2001, 107, 48.
53. For examples of Fe-diazoalkane interactions, see: (a) Bart, S. C.; Bowman, A. C.; Lobkovsky, E.; Chirik, P. J. J. Am. Chem. Soc. 2007, 129, 7212-7213.
54. (b) Russell, S. K.; Lobkovsky, E; Chirik, P. J. J. Am. Chem. Soc. 2009, 131, 36-37.
55. Z2 orbital, a π bond mediated by the dπ orbital, and half a π antibonding interaction due to the dπ' electron, which together translate to a bond order of 1.5.
56. See, e.g.: Ghosh, A.; Tangen, E.; Ryeng, H.; Taylor, P. R. Eur. J. Inorg. Chem. 2004, 23, 4555-4560.