Characterization of manganese(V)-oxo polyoxometalate intermediates and their properties in oxygen-transfer reactions

Journal of the American Chemical Society

Volumn 128, Issue 48, 2006, Pages 15451-15460

  Khenkin, Alex M ^a   Kumar, Devesh ^b   Shaik, Sason ^b   Neumann, Ronny ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

^b HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; COMPOSITION; ESTERS; GROUND STATE; NUCLEAR MAGNETIC RESONANCE; OXIDATION; SUBSTITUTION REACTIONS;

OXIDATION CATALYST; OXYGEN TRANSFER REACTIONS; POLYOXOMETALATES; TRIPLET TRANSITION STATES;

MANGANESE COMPOUNDS;

FLUOROBENZENE; IODOPENTAFLUOROBENZENE BIS(TRIFLUOROACETATE); MANGANESE; OXYGEN; POLYOXOMETALATE; PORPHYRIN; PROPYLENE; SOLVENT; TRANSITION ELEMENT; TRIFLUOROACETIC ACID; WATER;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; ENERGY; ENTHALPY; ENTROPY; EPOXIDATION; HYDROXYLATION; KINETICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; OXYGEN TRANSPORT; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; WARMING;

EID: 33845309696     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0638455     Document Type: Article

References (78)

1. (a) Hill, C. L.; Brown, R. B. J. Am. Chem. Soc. 1986, 108, 536-537.
2. (b) Mansuy, D.; Bartoli, J. F.; Battioni, P.; Lyon, D. K.; Finke, R. G. J. Am. Chem. Soc. 1991, 113, 7222-7229.
3. (a) Neumann, R.; Khenkin, A. M. Chem. Commun. 1998, 1967-1968.
4. (b) Neumann, R.; Gara, M. J. Am. Chem. Soc. 1994, 116, 5509-5510.
5. (c) Neumann, R.; Gara, M. J. Am. Chem. Soc. 1995, 117, 5066-5074.
6. (d) Neumann, R.; Juwiler, D. Tetrahedron 1996, 47, 8781-8788.
7. (e) Boesing, M.; Noeh, A.; Loose, I.; Krebs, B. J. Am. Chem. Soc. 1998, 120, 7252-7259.
8. Ben-Daniel, R.; Weiner, L.; Neumann, R. J. Am. Chem. Soc. 2002, 124, 8788-8789.
9. (a) Ortiz de Montellano, P. R., Ed.; Cytochrome P450: structure, mechanism and biochemistry, 2nd ed.; Plenum Press: New York, 1995.
10. (b) Ortiz de Montellano, P. R., Ed.; Cytochrome P450: structure, mechanism and biochemistry, 3rd ed.; Kluwer Academic/Plenum Publishers: New York, 2005.
11. (c) Groves, J. T. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 3569-3574.
12. (d) Sono, M.; Roach, M. P.; Coulter, E. D.; Dawson, J. H. Chem. Rev. 1996, 96, 2841-2887.
13. (e) Groves, J. T.; Han, Y. Z. Models and mechanisms of Cytochrome P450 action. In ref 3a, Chapter 1, p 3.
14. (f) Harris, D. L. Curr. Opin. Chem. Biol. 2001, 5, 724-735.
15. (g) Shaik, S.; Kumar, D.; de Visser, S. P.; Ahmet, A.; Thiel, W. Chem. Rev. 2005, 105, 2279-2328.
16. (a) Kumar, D.; Derat, E.; Khenkin, A. M.; Neumann, R.; Shaik, S. J. Am. Chem. Soc. 2005, 127, 17712-17718.
17. (b) de Visser, S. P.; Kumar, D.; Neumann, R.; Shaik, S. Angew. Chem., Int. Ed. 2004, 43, 5661-5665.
18. (a) Groves, J. T.; Stern, M. K. J. Am. Chem. Soc. 1984, 109, 3812-3814.
19. (b) Arasasingham, R. D.; He, G. X.; Bruice, T. C. J. Am. Chem. Soc. 1993, 115, 7985-7991.
20. (c) Groves, J. T.; Lee, J.; Marla, S. S. J. Am. Chem. Soc. 1997, 119, 6269-6273.
21. (d) Zhang, R.; Newcomb, M. J. Am. Chem. Soc. 2003, 125, 12418-12419.
22. (e) Zhang, R.; Horner, J. H.; Newcomb, M. J. Am. Chem. Soc. 2005, 127, 6573-6582.
23. (f) Zhang, R.; Harischandra, D. N.; Newcomb, M. Chem. - Eur. J. 2005, 11, 5713-5720.
24. (a) Feichtinger, D.; Plattner, D. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 1718-1719.
25. (b) Feichtinger, D.; Plattner, D. A. Perkin 2 2000, 1023-1028.
26. (d) Li, Z.; Tang, Z. H.; Hu, X. X.; Xia, C. G. Chem. - Eur. J. 2005, 11, 1210-1216.
27. (d) Khavrutskii, I. V.; Musaev, D. G.; Morokuma, K. Inorg. Chem. 2005, 44, 306-315.
28. (a) Gross, Z.; Golubkov, G.; Simkhovich, L. Angew. Chem., Int. Ed. 2000, 39, 4045-4047.
29. (b) Wang, S. H.; Mandimutsira, B. S.; Todd, R.; Randhanie, B.; Fox, J. P.; Goldberg, D. P. J. Am. Chem. Soc. 2004, 126, 18-19.
30. (a) Mandimutsira, B. S.; Randhanie, B.; Todd, R. C.; Wang, H.; Zareba, A. A.; Czernuszewicz, R. S.; Goldberg, D. P. J. Am. Chem. Soc. 2002, 124, 15170-15171.
31. (b) Lansky, D. E.; Mandimutsira, B.; Ramdhanie, B.; Clausen, M.; Penner-Hahn, J.; Zvyagin, S. A.; Telser, J.; Krzystek, J.; Zhan, R.; Ou, Z.; Kadish, K. M.; Zakharov, L.; Rheingold, A. L.; Goldberg, D. P. Inorg. Chem. 2005, 44, 4485-4498.
32. (a) Collins, T. J.; Powell, R. D.; Slebodnick, C.; Ufellman, E. S. J. Am. Chem. Soc. 1990, 112, 899-901.
33. (b) Collins, T. J.; Gordon-Wylie, S. W. J. Am. Chem. Soc. 1989, 111, 4511-4513.
34. (c) Workman, J. M.; Powell, R. D.; Procyk, A. D.; Collins, T. J.; Bocian, D. F. Inorg. Chem. 1992, 31, 1548-1550.
35. (d) Gilbert, B. C.; Kamp, N. W. J.; Lindsay-Smith, J. R.; Oakes, J. J. Chem. Soc., Perkin. Trans. 2 1998, 1841-1844.
36. (a) Zhang, X. Y.; Pope, M. T. J. Mol. Catal. A 1996, 114, 201-208.
37. (b) Zhang, X.-Y.; Jameson, G. B.; O'Connor, C. J.; Pope, M. T. Polyhedron 1996, 15, 917-922.
38. (c) Zhang, X.-Y.; O'Connor, C. J.; Jameson, G. B.; Pope, Michael T. Inorg. Chern. 1996, 35, 30-34.
39. (d) Zhang, X. Y.; Pope, M. T.; Chance, M. R.; Jameson, G. B. Polyhedron 1995, 14, 1381-1392.
40. Adam, W.; Haas, W.; Lohray, B. B. J. Am. Chem. Soc. 1991, 113, 6202-6208.
41. As a reviewer noted, a diamagnetic species could conceivably also arise from an antiferromagnetically coupled Mn(IV)-O-Mn(IV) dimer. Although this is possible, we observed no EPR signal even down to 6 K. Also, we feel that we can exclude this assignment of the narrow peaks because the diamagnetic species is not persistent in the presence of oxygen acceptors (substrates), although one would expect the opposite for a Mn-(IV)-O-Mn(IV) dimer; it should be quite stable in solution. Furthermore, one would expect the Mn(IV)-O-Mn(IV) dimer to be a poor oxygen donor especially since it has already been shown that even monomeric Mn(IV)-O species are not reactive (ref 10).
42. (a) Nam, W.; Valentine, J. S. J. Am. Chem. Soc. 1993, 115, 1772-1778.
43. (b) Groves, J. T.; Kruper, W. J. J. Am. Chem. Soc. 1979, 101, 7613-7615.
44. (c) Leising, R. A.; Brennan, B. A.; Que, L.; Munck, E. J. Am. Chem. Soc. 1991, 113, 3988-3990.
45. Brown, G. M.; Noe-Spirlet, M. R.; Busing, W. R.; Levy, H. A. Acta Crystallogr., B 1977, 34, 1038-1046.
46. (a) Ghosh, A.; Persson, B. J.; Taylor, P. R. J. Biol. Inorg. Chem. 2003, 8, 507-511.
47. (b) Ghosh, A.; Taylor, P. R. Curr. Opin. Chem. Biol. 2003, 7, 113-124.
48. (a) Becke, A. D. Phys. Rev. A 1988, 36, 3098-3100.
49. (b) Perdew, J. P. Phys. Rev. B 1986, 33, 8822-8824.
50. (c) Li, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1998-I, 37, 785-789.
51. (d) Perdew, J. P.; Wang, Y. Phys. Rev. B 1992, 45, 13245-13249.
52. (e) Reiher, M.; Salomon, O.; Hess, B. A. Theor. Chem. Acc. 2001, 107, 48-55.
53. (a) It has been noted in the past that while hybrid functionals are usually better than pure functionals, they can show occasionally increased stabilization of high spin states: cf. Salomon, O.; Reiher, M.; Hess, B.A. J. Chem. Phys. 2002, 117, 4729-4737.
54. Harvey, J. N. Struct. Bonding 2004, 112, 151-183.
55. Smith, D. M.; Dupuis, M.; Straasma, T. P. Mol. Phys. 2005, 103, 273-278.
56. (b) The use of a pure functional has also been recently shown to better fit the experimentally observed spin states for a Mn(V)= O porphyrin; cf. De Angelis, F.; Jin, N.; Car, R. Groves, J. T. Inorg. Chem. 2006, 45, 4268-4276.
57. (a) Shaik, S; Cohen, S.; de Visser, S. P.; Sharma, P. K.; Kumar, D.; Kozuch, S.; Ogliaro, F; Danovich, D. Eur. J. Inorg. Chem. 2004, 35, 207-226.
58. (b) Shaik, S.; de Visser, S. P.; Ogliaro, F.; Schwarz, H.; Schröder, D. Curr. Opin. Chem. Biol. 2002, 6, 556-567.
59. (c) Shaik, S.; Filatov, M.; Schröder, D.; Schwarz, H. Chem. - Eur. J. 1998, 4, 193.
60. (d) Danovich, D.; Shaik, S. J. Am. Chem. Soc. 1997, 119, 1773-1786.
61. Kumar, D.; Hirao, H.; Que, L.; Shaik, S. J. Am. Chem. Soc. 2005, 127, 8026-8027.
62. (a) Bryant, J. R.; Mayer, J. M. J. Am. Chem. Soc. 2003, 125, 10351-10361.
63. (b) Lide, D. R., Ed. Handbook of Chemistry and Physics; CRC Press: Boca Raton, FL, 1997; pp 9-64.
64. (a) de Visser, S. P.; Ogliaro, F.; Sharma, P. K.; Shaik, S. J. Am. Chem. Soc. 2002, 124, 11809-11826.
65. (b) See ref 3g.
66. (a) Groves, J. T.; Lee, J.; Maria, S. S. J. Am. Chem. Soc. 1997, 119, 6269-6270.
67. (b) Jin, N.; Groves, J. T. J. Am Chem. Soc. 1999, 121, 2923-2924.
68. Lyon, D. K.; Miller, W. K.; Novet, T.; Domaille, P. J.; Evitt, E.; Johnson, D. C.; Finke, R. G. J. Am. Chem. Soc. 1991, 113, 7209-7221.
69. (a) Becke, A. D. J. Chem. Phys. 1992, 96, 2155-2160.
70. (b) Becke, A. D. J. Chem. Phys. 1992, 97, 9173-9177.
71. (c) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
72. (d) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
73. LACVP is derived from LANL2DZ; see: Dunning, T. H., Jr.; Hay, P. J. In Modern Theoretical Chemistry; Schaefer, H. F., III, Ed.; Plenum: New York, 1976; pp 1-28.
74. Jaguar 5.5; Schrödinger, Inc.: Portland, OR, 2003.
75. Frisch, M. J.; et al. Gaussian 03, Revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
76. See for example: (a) Quinonero, D.; Wang, Y.; Morokuma, K.; Khavrutskii, L. A.; Botar, B.; Geletti, Y. V.; Hill, C. L.; Musaev, D. G. J. Phys. Chem. B 2006, 110, 170-173.
77. (b) Musaev, D. G.; Morokuma, K.; Geletii, Y. V.; Hill, C. L Inorg. Chem. 2004, 43, 7702-7708.
78. (c) For, a recent interplay of DFT and experiment, see: Anderson, T. M.; Neiwert, W. A.; Kirk, M. L.; Piccoli, P. M. B.; Schultz, A. J.; Koetzle, T. E.; Musaev, D. G.; Morokuma, K.; Cao, R.; Hill, C. L. Science 2004, 306, 2074-2077.