A two-state reactivity rationale for counterintuitive axial ligand effects on the C-H activation reactivity of nonheme FeIV=O oxidants

Chemistry - A European Journal

Volumn 14, Issue 6, 2008, Pages 1740-1756

  Hirao, Hajime ^a   Que Jr , Lawrence ^b   Nam, Wonwoo ^c   Shaik, Sason ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^b UNIVERSITY OF MINNESOTA   (United States)

^c Ewha Womans University   (South Korea)

Author keywords

C H activation; Density functional calculations; Homogeneous catalysis; Iron oxo complexes; Oxidation; Two state reactivity

Indexed keywords

ABSTRACTING; ACTIVATION ANALYSIS; BLENDING; CATALYSIS; CHEMICAL ACTIVATION; DENSITY FUNCTIONAL THEORY; GROUND STATE; IRON OXIDES; OXIDANTS; OXIDATION; PHOSPHORUS COMPOUNDS; SPIN DYNAMICS;

1 ,4-CYCLOHEXADIENES; C-H ACTIVATION; DFT/B3LYP CALCULATIONS; HOMOGENEOUS CATALYSIS; IRON-OXO COMPLEXES; REACTIVITY PATTERN; TWO-STATE REACTIVITY; VARIABLE TRANSMISSION;

EXCITED STATES;

EID: 48749089759     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200701739     Document Type: Article

References (75)

1. M. Sono, M. P. Roach, E. D. Coulter, J. H. Dawson, Chem. Rev. 1996, 96, 2841-2888.
2. J. T. Groves in Cytochrome P450: Structure, Mechanism, and Biochemistry, 3rd ed. (Ed.: P. R. Ortiz de Montellano), Kluwer-Academic/ Plenum, New York, 2005, pp 1-43.
3. I. Schlichting, J. Berendzen, K. Chu, A. M. Stock, S. A. Maves, D. E. Benson, R. M. Sweet, D. Ringe, G. A. Petsko, S. G. Sligar, Science 2000, 287, 1615-1622.
4. T. Spolitak, J. H. Dawson, D. P. Ballou, J. Biol. Chem. 2005, 280, 20300-20309.
5. I. G. Denisov, T. M. Makris, S. G. Sligar, J. Biol. Chem. 2001, 276, 11648-11652.
6. T. S. Dowers, D. A. Rock, D. A. Rock, J. P. Jones, J. Am. Chem. Soc. 2004, 126, 8868-8869.
7. D. L. Harris, Curr. Opin. Chem. Biol. 2001, 5, 724-735.
8. J. C. Price, E. W. Barr, T. E. Glass, C. Krebs, J. M. Bollinger, Jr., J. Am. Chem. Soc. 2003, 125, 13008-13009.
9. J. C. Price, E. W. Barr, B. Tirupati, J. M. Bollinger, Jr., C. Krebs, Biochemistry 2003, 42, 7497-7508.
10. D. A. Proshlyakov, T. F. Henshaw, G. R. Monterosso, M.J. Ryle, R. P. Hausinger, J. Am. Chem. Soc. 2004, 126, 1022-1023.
11. L. M. Hoffart, E. W. Barr, R. B. Guyer, J. M. Bollinger, Jr., C. Krebs, Proc. Natl. Acad. Sci. USA 2006, 103, 14738-14743.
12. D. P. Galonic, E. W. Barr, C. T. Walsh, J. M. Bollinger, Jr., C. Krebs, Nat. Chem. Biol. 2007, 3, 113-116.
13. J.-U. Rohde, J.-H. In, M. H. Lim, W. W. Brennessel, M. R. Bukowski, A. Stubna, E. Münck, W. Nam, L. Que, Jr., Science 2003, 299, 1037-1039.
14. a) M. Costas, M. P. Mehn, M. P. Jensen, L. Que, Jr., Chem. Rev. 2004, 104, 939-986;
15. b) W. Nam, Acc. Chem. Res 2007, 40, 522-531.
16. X. Shan, L. Que, Jr. J. Inorg. Biochem. 2006, 100, 421-433.
17. J. Kaizer, E. J. Klinker, N. Y. Oh, J.-U. Rohde, W. J. Song, A. Stubna, J. Kim, E. Münck, W. Nam, L. Que, Jr. J. Am. Chem. Soc. 2004, 126, 472-473.
18. V. Balland, M.-F. Charlot, F. Banse, J.-J. Girerd, T. A. Mattioli, E. Bill, J.-F. Bartoli, P. Battioni, D. Mansuy, Eur. J. Inorg. Chem. 2004, 2, 301-308.
19. M. Martinho, F. Banse, J.-F. Bartoli, T. A. Mattioli, P. Battioni, O. Horner, S. Bourcier, J.-J. Girerd, Inorg. Chem. 2005, 44, 9592-9596.
20. N. Y. Oh, Y. Suh, M. J. Park, M. S. Seo, J. Kim, W. Nam, Angew. Chem. 2005, 117, 4307-4311;
21. Angew. Chem. Im. Ed. 2005, 44, 4235-4239.
22. T. K. Paine, M. Costas, J. Kaizer, L. Que, Jr., J. Biol. Inorg. Chem. 2006, 11, 272-276.
23. M. H. Lim, J.-U. Rohde, A. Stubna, M. R. Bukowski, M. Costas, R. Y. N. Ho, E. Münck, W. Nam, L. Que, Jr., Proc. Natl. Acad. Sci. USA 2003, 100, 3665-3670.
24. S. O. Kim, C. V. Sastri, M. S. Seo, J. Kim, W. Nam, J. Am. Chem. Soc. 2005, 127, 4178-4179.
25. C. V. Sastri, M. J. Park, T. Ohta, T. A. Jackson, A. Stubna, M. S. Seo, J. Lee, J. Kim, T. Kitagawa, E. Munck, L. Que, Jr., W. Nam, J. Am. Chem. Soc. 2005, 127, 12494-12495.
26. C. V. Sastri, M. S. Seo, M. J. Park, K. M. Kim, W. Nam, Chem. Commun. 2005, 1405-1407.
27. M. You, M. S. Seo, K. M. Kim, W. Nam, J. Kim, Bull. Korean Chem. Soc. 2006, 27, 1140-1144.
28. C. V. Sastri, J. Lee, K. Oh, Y. J. Lee, J. Lee, T. A. Jackson, K. Ray, H. Hirao, W. Shin, J. A. Halfen, J. Kim, L. Que, Jr., S. Shaik, W. Nam, Proc. Natl. Acad. Sci. USA, 2007, 104, 19181-19186.
29. J.-U. Rohde, L. Que, Jr., Angew. Chem. 2005, 117, 2295-2298;
30. Angew. Chem. Int. Ed. 2005, 44, 2255-2258.
31. M. R. Bukowski, K. D. Koehntop, A. Stubna, E. L. Bominaar, J. A. Halfen, E. Münck, W. Nam, L. Que, Jr., Science 2005, 310, 1000-1002.
32. A. Decker, E. I. Solomon, Angew. Chem. 2005, 117, 2292-2295;
33. Angew. Chem. Int. Ed. 2005, 44, 2252-2255.
34. H. Hirao, D. Kumar, L. Que, Jr., S. Shaik, J. Am. Chem. Soc. 2006, 128, 8590-8606.
35. S. P. de Visser, J. Am. Chem. Soc. 2006, 128, 15809-15818.
36. Jaguar 5.5, Schrödinger, Inc., Portland, Oregon, 2004.
37. M. J. Frisch, et al. Gaussian 03, Revision C.02. Gaussian, Inc., Wallingford CT, 2004.
38. a) A. D. Becke, J. Chem. Phys. 1992, 96, 2155-2160;
39. b) A. D. Becke, J. Chem. Phys. 1992, 97, 9173-9177;
40. c) A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652;
41. d) C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789.
42. The LACVP series is derived from LANL2DZ, see: a) J. P. Hay, W. R. Wadt, J. Chem. Phys. 1985, 82, 299-310;
43. b) R. A. Friesner, R. B. Murphy, M. D. Beachy, M. N. Ringnalda, W. T. Pollard, B. D. Dunietz, Y. Cao, J. Phys. Chem. A 1999, 103, 1913-1928.
44. H. Hirao, D. Kumar, S. Shaik, J. Inorg. Biochem. 2006, 100, 2054-2068.
45. a) P. Flükiger, H. P. Lüthi, S. Portmann, J. Weber, Mokelel 4.3 and 5.1.0, Swiss Center for Scientific Computing, Manno, Switzerland, 2000-2002;
46. b) S. Portmann, H. P. Lüthi, CHIMIA 2000, 54, 766-770.
47. C. Adamo, V. Barone, J. Chem. Phys. 1999, 110, 6158-6170.
48. a) A. Fouqueau, M. E. Casida, L. M. Lawson Daku, A. Houser, F. Neese, J. Chem. Phys. 2005, 122, 044110/1-044110/13;
49. b) F. Neese, J. Inorg. Biochem. 2006, 100, 716-726;
50. c) J. C. Schnöboom, F. Neese, W. Thiel, J. Am. Chem. Soc. 2005, 127, 5840-5853.
51. M. Reiher, O. Salomon, B. A. Hess, Theor. Chem. Acc. 2001, 107, 48-55.
52. a) M. Dolg, U. Wedig, H. Stoll, H. Preuss, J. Chem. Phys. 1987, 86, 866-872;
53. b) A. J. H. Wachters, J. Chem. Phys. 1970, 52, 1033-1036;
54. c) C. W. Bauschlicher, Jr., S. R. Langhoff, L. A. Barnes, J. Chem. Phys. 1989, 91, 2399-2411.
55. B. J. Lynch, Y. Zhao, D. G. Truhlar, J. Phys. Chem. A 2003, 107, 1384-1388.
56. D. J. Tannor, B. Marten, R. Murphy, R. A. Friesner, D. Sitkoff, A. Nicholls, M. Ringnalda, W. A. Goddard, III, B. Honig, J. Am. Chem. Soc. 1994, 116, 11875-11882.
57. S. P. de Visser, F. Ogliaro, P. K. Sharma, S. Shaik, J. Am. Chem. Soc. 2002, 124, 11 809-11 826.
58. L. Melander, W. H. Saunders, Jr., Reaction Rates of Isotopic Molecules, Robert E. Krieger Publishing Company, Malabar, Florida, 1987.
59. H. Hirao, D. Kumar, W. Thiel, S. Shaik, J. Am. Chem. Soc. 2005, 127, 13007-13018.
60. D. Kumar, H. Hirao, L. Que, Jr., S. Shaik, J. Am. Chem. Soc. 2005, 127, 8026-8027.
61. S. Shaik, D. Kumar, S. P. de Visser, A. Altun, W. Thiel, Chem. Rev. 2005, 105, 2279-2328.
62. 3, the second electron shifts to π*.
63. D. Danovich, S. Shaik, J. Am. Chem. Soc. 1997, 119, 1773-1786.
64. For some applications and generalizations in organometallic chemistry see: a) J. N. Harvey, M. Aschi, Faraday Discuss. 2003, 124, 129-143;
65. b) R. Poli, J. N. Harvey, Chem. Soc. Rev. 2003, 32, 1.-8;
66. c) J. N. Harvey, Phys Chem. Chem. Phys. 2007, 9, 331-343;
67. d) S. Shaik, D. Danovich, D. Schröder, H. Schwarz, Helv. Chim. Acta 1995, 78, 1393-1407;
68. e) D. Schröder, S. Shaik, H. Schwarz, Acc. Chem. Res. 2000, 33, 131-175;
69. f) S. Shaik, H. Hirao, D. Kumar, Acc. Chem. Res. 2007, 40, 532-542.
70. +, see: M. Filatov, S. Shaik, J. Phys. Chem. A 1998, 102, 3835-3846.
71. a) P. K. Sharma, S. P. de Visser, F. Ogliaro, S. Shaik, J. Am. Chem. Soc. 2003, 125, 2291-2300;
72. b) S. P. de Visser, F. Ogliaro, Z. Gross, S. Shaik, Chem. Eur. J. 2001, 7, 5954-5960.
73. a) See for example, the KIE in a similar process (H-migration) where the TS lies close in energy to the reactant. R. Schork, H. Koppel, J. Chem. Phys. 2001, 115, 7907-7923.
74. b) Solvent relaxation has to be taken into account as well in the consideration of the barrier on the quintet state vis-à-vis the ZPE of the C-H vibration. Some of the solvent effect on the barrier is determined by polarization and has to be taken into account in such a consideration. However, the slow reorganization modes of the solvent are expected to follow after the molecular tunnel. This breakdown is not simple for the present computational data.
75. S. P. de Visser, J. Am. Chem. Soc. 2006, 128, 9813-9824.