Peroxovanadate Imidazole Complexes as Catalysts for Olefin Epoxidation: Density Functional Study of Dynamics, 51V NMR Chemical Shifts, and Mechanism

Journal of the American Chemical Society

Volumn 126, Issue 10, 2004, Pages 3310-3320

  Bühl, Michael ^a   Schurhammer, Rachel ^a,b   Imhof, Petra ^a,c  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

^b UNIVERSITÉ DE STRASBOURG   (France)

^c UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; COMPUTER SIMULATION; MOLECULAR DYNAMICS; PROBABILITY DENSITY FUNCTION; SOLUTIONS;

EPOXIDATION; TRANSITION STATES;

OLEFINS;

ALKENE; IMIDAZOLE DERIVATIVE; PEROXOVANADATE IMIDAZOLE; UNCLASSIFIED DRUG; VANADIC ACID;

AQUEOUS SOLUTION; ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; EPOXIDATION; GAS ANALYSIS; HYDROGEN BOND; LIQUID; MAGNETISM; NUCLEAR MAGNETIC RESONANCE; OXIDATION; OXYGEN TRANSPORT; SOLVATION; STRUCTURE ANALYSIS;

EID: 84961983976     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja039436f     Document Type: Article

References (110)

1. For example: (a) Barton, D., Martell, A. E., Sawyer, D. T., Eds. The Activation of Dioxygen and Homogeneous Catalytic Oxidation; Plenum Press: New York, 1993.
2. (b) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879-2932.
3. Brégeault, J.-M. Dalton Trans. 2003, 3289-3302.
4. For example: (a) Meunier, B., Ed. Biomimetic Oxidations Catalyzed by Transition Metal Complexes; Imperial College Press: London, 2000.
5. (b) Gamez, P.; Aubel, P. G.; Driessen, W. L.; Reedijk, J. Chem. Soc. Rev. 2001, 30, 376-385.
6. Oxidations with vanadium complexes: Ligtenbarg, A. G. J.; Hage, R.; Feringa, B. L. Coord. Chem. Rev. 2003, 237, 89-101.
7. Ortiz de Montellano, P. R., Ed. Cyctochrome P450: Structure, Mechanisms, and Biochemistry, 2nd ed.; Plenum Press: New York, 1995.
8. (a) Karlin, K. D., Tyeklár, Z., Eds. Bioinorganic Chemistry of Copper; Chapman & Hall: New York, 1993.
9. (b) Klinmann, J. P. Chem. Rev. 1996, 96, 2541-2561.
10. (c) Solomon, E. I.; Sundaram, U. M.; Machonkin, T. E. Chem. Rev. 1996, 96, 2563-2606.
11. Butler, A.; Baldwin, A. H. Struct. Bonding 1997, 89, 109.
12. (a) Crans, D. C. In Metal Ions in Biological Systems; Sigel, H., Sigel, A., Eds.; Marcel Dekker: New York, 1995; Vol. 31, pp 147-210.
13. (b) Tracey, A. S., Crans, D. C., Eds. Vanadium Compounds - Chemistry, Biochemistry, and Therapeutic Applications; ACS Symposium Series, Vol. 711; American Chemical Society: Washington, DC, 1998.
14. Review: Rehder, D. Inorg. Chem. Commun. 2003, 6, 604-617.
15. Thompson, K. H.; McNeill, J. H.; Orvig, C. Chem. Rev. 1999, 99, 2561-2571.
16. Review: Dembitsky, V. M. Tetrahedron 2003, 59, 4701-4720.
17. (a) Messerschmidt, A.; Wever, R. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 392-396.
18. (b) Messerschmidt, A.; Prade, L.; Wever, R. Biol. Chem. 1997, 378, 309-315.
19. (a) Rehder, D. Coord. Chem. Rev. 1999, 182, 297-322.
20. (b) Rehder, D.; Santoni, G.; Licini, G. M.; Schulzke, C.; Meier, B. Coord. Chem. Rev. 2003, 237, 53-63.
21. Crans, D. C.; Keramidas, A. D.; Hoover-Litty, H.; Anderson, O. P.; Miller, M. M.; Lemoine, L. M.; Pleasic-Williams, S.; Vandenberg, M.; Rossomando, A. J.; Sweet, L. J. J. Am. Chem. Soc. 1997, 119, 5447-5448.
22. (a) Andersson, I.; Angus-Dunne, S.; Howart, O.; Pettersson, L. J. Inorg. Biochem. 2000, 80, 51-58.
23. (b) Review: Pettersson, L.; Andersson, I.; Gorzsás, A. Coord. Chem. Rev. 2003, 237, 77-87.
24. With His or 3,5-dimethylpyrazole as coligands: Mukherjee, J.; Ganguly, S.; Bhattacharjee, M. Indian J. Chem., Sect. A 1996, 35, 471.
25. Glas, H.; Herdtweck, E.; Artus, G. R. J.; Thiel, W. R. Inorg. Chem. 1998, 37, 3644.
26. See, for instance: Rehder, D. In Transition Metal Nuclear Magnetic Resonance; Pregosin, P. S., Ed.; Elsevier: Amsterdam, 1991; pp 1-58.
27. (a) Bühl, M.; Parrinello, M. Chem.-Eur. J. 2001, 7, 4487-4494.
28. (b) Bühl, M.; Mauschick, F. T.; Terstegen, F.; Wrackmeyer, B. Angew. Chem., Int. Ed. 2002, 41, 2312-2315.
29. (c) Bühl, M.; Mauschick, F. Phys. Chem. Chem. Phys. 2002, 4, 5508-5514.
30. (d) Bühl, M. J. Phys. Chem. A 2002, 106, 10505-10509.
31. Bühl, M.; Mauschick, F. T.; Schurhammer, R. In High Performance Computing in Science and Engineering, Munich 2002; Wagner, S., Hanke, W., Bode, A., Durst, F., Eds.; Springer: Berlin, 2003; pp 189-199.
32. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratman, 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.; Baboul, A. G.; Stefanov, B. B.; Liu, C.; 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. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzales, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98; Gaussian, Inc.: Pittsburgh, PA, 1998.
33. Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100.
34. Perdew, J. P. Phys. Rev. B 1986, 33, 8822-8824. Perdew, J. P. Phys. Rev. B 1986, 34, 7406.
35. Perdew, J. P. Phys. Rev. B 1986, 33, 8822-8824. Perdew, J. P. Phys. Rev. B 1986, 34, 7406.
36. (a) Wachters, A. J. H. J. Chem. Phys. 1970, 52, 1033-1036.
37. (b) Hay, P. J. J. Chem. Phys. 1977, 66, 4377-4384
38. (a) Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257-2261.
39. (b) Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213-222.
40. See, for instance: Koch, W.; Holthausen, M. C. A Chemist's Guide to Density Functional Theory; Wiley-VCH: Weinheim, 2000, and the extensive bibliography therein.
41. Clark, T.; Chandrasekhar, J.; Spitznagel, G. W.; Schleyer, P. v. R. J. Comput. Chem. 1983, 4, 294.
42. Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553-566.
43. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03; Gaussian, Inc.: Pittsburgh, PA, 2003.
44. Car, R.; Parrinello, M. Phys. Rev. Lett. 1985, 55, 2471-2474.
45. Hutter, J.; Alavi, A.; Deutsch, T.; Bernasconi, M.; Goedecker, S.; Marx, D.; Tuckerman, M.; Parrinello, M. CPMD Version 3.3a; Max-Planck-Institut für Festkörperforschung and IBM Research Laboratory (1995-1999).
46. Troullier, N.; Martins, J. L. Phys. Rev. B 1991, 43, 1993-2006.
47. Kleinman, L.; Bylander, D. M. Phys. Rev. Lett. 1982, 48, 1425-1428.
48. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
49. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899-926.
50. 3: Bühl, M.; Steinke, T.; Schleyer, P. v. R.; Boese, R. Angew. Chem., Int. Ed. Engl. 1991, 30, 1160-1161.
51. s symmetry with θ = 180°, which is a transition state 0.7 kcal/mol above 1.
52. Bühl, M.; Hamprecht, F. A. J. Comput. Chem. 1998, 119, 113-122.
53. (a) Bühl, M. J. Comput. Chem. 1999, 20, 1254-1261.
54. (b) Bühl, M. J. Inorg. Biochem. 2000, 80, 137-139.
55. 2) bond length: On going from the gas phase into aqueous solution, this bond contracts from 2.279 to 2.017 Å, that is, by 0.26 Å, at the BP86 level (present work), and from 2.394 to 2.082 Å, that is, by 0.31 Å, with the BLYP functional (ref 19a).
56. (a) Smith, T. S., II; Root, C. A.; Kampf, J. W.; Rasmussen, P. G.; Pecorano, V. L. J. Am. Chem. Soc. 2000, 122, 767-775.
57. (b) Saladino, A. C.; Larsen, S. C. J. Phys. Chem. A 2002, 106, 10444-10451.
58. From a rigid scan with all other parameters fixed to the values in the CP-opt geometry of 1.
59. Jameson, C. J.; Rehder, D.; Hoch, M. J. Am. Chem. Soc. 1987, 109, 2589-2594. This empirical value has been qualitatively reproduced using theoretical methods similar to those employed in the present study, see: Godbout, N.; Oldfield, E. J. Am. Chem. Soc. 1997, 119, 8065-8069.
60. Jameson, C. J.; Rehder, D.; Hoch, M. J. Am. Chem. Soc. 1987, 109, 2589-2594. This empirical value has been qualitatively reproduced using theoretical methods similar to those employed in the present study, see: Godbout, N.; Oldfield, E. J. Am. Chem. Soc. 1997, 119, 8065-8069.
61. Adam, W., Ed. Peroxide Chemistry; Wiley-VCH: Weinheim, 2000.
62. Mo, for example: (a) Kühn, F. E.; Groarke, M.; Bencze, E.; Prazeres, A.; Santos, A. M.; Calhorda, M. J.; Romao, C. C.; Goncalves, I. S.; Lopes, A. D.; Pillinger, M. Chem.-Eur. J. 2002, 8, 2370-2383.
63. (b) Deubel, D. V.; Sundermeyer, J.; Frenking, G. Eur. J. Inorg. Chem. 2001, 1819-1827.
64. (c) Deubel, D. V.; Sundermeyer, J.; Frenking, G. Org. Lett. 2001, 3, 329-332.
65. (d) Hroch, A.; Gemmecker, G.; Thiel, W. R. Eur. J. Inorg. Chem. 2000, 1107-1114.
66. (e) Deubel, D. V.; Sundermeyer, J.; Frenking, G. J. Am. Chem. Soc. 2000, 122, 10101-10108.
67. Re: (a) Gisdakis, P.; Yudanov, I. V.; Rösch, N. Inorg. Chem. 2001, 40, 3755-3765.
68. (b) Görling, A.; Trickey, S. B.; Gisdakis, P.; Rösch, N. Top. Organomet. Chem. 1999, 4, 109-164.
69. Mn: (a) Cavallo, L.; Jacobsen, H. J. Org. Chem. 2003, 68, 6202-6207.
70. (b) Adam, W.; Roschmann, K. J.; Saha-Möller, C. R.; Seebach, D. J. Am. Chem. Soc. 2002, 124, 5068-5073.
71. Cr: Rappe, A. K.; Li, S. J. Am. Chem. Soc. 2003, 125, 11188-11189.
72. Ti: (a) Sever, R. R.; Root, T. W. J. Phys. Chem. B 2003, 107, 4090-4099.
73. (b) Cui, M.; Adam, W.; Shen, J. H.; Luo, X. M.; Tan, X. J.; Chen, K. X.; Ji, R. Y.; Jiang, H. L. J. Org. Chem. 2002, 67, 1427-1435.
74. Fe: (a) Musaev, D. G.; Basch, H.; Morokuma, K. J. Am. Chem. Soc. 2002, 124, 4235-4148.
75. (b) de Visser, S. P.; Ogliaro, F.; Harris, N.; Shaik, S. J. Am. Chem. Soc. 2001, 123, 3037-3047.
76. +, see: Garcia, L.; Sambrano, J. R.; Safont, V. S.; Calatayud, M.; Beltrán, A.; Andrés, J. J. Phys. Chem. A 2003, 107, 3107-3120.
77. Sheldon, R. A. Recl. Trav. Chim. Pays-Bas 1973, 253, 367.
78. Sharpless, K. B.; Townsend, J. M.; Williams, D. R. J. Am. Chem. Soc. 1972, 94, 295.
79. Mimoun, H.; Seree de Roch, I.; Sajus, L. Tetrahedron 1970, 26, 37.
80. - + Im) is computed to be only 10.7 kcal/mol at the BP86/AE1 level. It has been noted in part 1, however, that in aqueous solution the bonding between V and Im is substantially reinforced (see V-N bond lengths in Table 1).
81. VN = 2.15 Å): Szentivanyi, H.; Stomberg, R. Acta Chem. Scand. A 1983, 37, 553.
82. 2: Shoemaker, C. B.; Shoemaker, D. P.; McAfee, L. V.; DeKock, C. W. Acta Crystallogr., Sect. C 1985, 41, 347.
83. Martin-Zarza, P.; Gili, P.; Rodriguez-Romero, P. V.; Ruiz-Peres, C.; Solans, X. Inorg. Chim. Acta 1994, 223, 173.
84. -: Piquemal, J.-Y.; Halut, S.; Brégeault, J.-M. Angew. Chem., Int. Ed. 1998, 37, 1146-1149.
85. The barrier for transfer of the oxo ligand O1 to the olefin is much higher, ca. 60 kcal/mol (BP86/AE1 + ZPE level).
86. The product of this process, hydroperoxy complex 7, is a stable minimum, unlike the elusive hydroperoxy complex 4, which would have a higher coordination number (see Scheme 2).
87. As implemented in Gaussian 98, cf.: (a) Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, 117-129.
88. (b) Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 106, 5151-5158.
89. (c) Barone, V.; Cossi, M.; Tomasi, J. J. Chem. Phys. 1997, 107, 3210-3221.
90. Review: (d) Tomasi, J.; Persico, M. Chem. Rev. 1994, 94, 2027-2094.
91. We explored a few other possibilities, such as proton transfer from the hydroperoxo to the hydroxo group in 7, but no transition state lower in energy than TS79 was found.
92. 2, 22 kcal/mol). Elimination of ozone is indicated to be even less favorable.
93. For Mo species following the insertion pathway, an additional reaction channel would be accessible, elimination of acetaldehyde rather than the epoxide from the metalla-oxalane (cf., ref 45e); we did not explore this possibility for 8, as its formation is strongly disfavored in the first place.
94. Balcells, D.; Maseras, F.; Lledós, A. J. Org. Chem. 2003, 68, 4265-4274.
95. For instance Im derivatives: Sundberg, R. J.; Martin, R. B. Chem. Rev. 1974, 74, 471-517.
96. Thiel, W. R.; Eppinger, J. Chem.-Eur. J. 1997, 5, 696-705.
97. (a) Bönnemann, H.; Brijoux, W.; Brinkmann, R.; Meurers, W.; Mynott, R.; von Philipsborn, W.; Egolf, T. J. Organomet. Chem. 1984, 272, 231.
98. (b) Fornika, R.; Görls, H.; Seeman, B.; Leitner, W. J. Chem. Soc., Chem. Commun. 1995, 1479-1480.
99. For example: (a) DeShong, P.; Slough, G. A.; Sidler, D. R.; Rybczynski, P. J.; von Philipsborn, W.; Kunz, R. W.; Bursten, B. E.; Clayton, T. W. J. Organometallics 1989, 8, 1381-1388.
100. (b) Koller, M.; von Philipsborn, W. J. Organometallics 1992, 11, 467-468.
101. Review: von Philipsborn, W. Chem. Soc. Rev. 1999, 95-106.
102. (a) Bühl, M. Organometallics 1997, 16, 261-267.
103. (b) Bühl, M. Angew. Chem., Int. Ed. 1998, 37, 142-144.
104. (c) Bühl, M. Organometallics 1999, 18, 4894-4896.
105. Wiberg, K. Tetrahedron 1968, 24, 1083-1096.
106. George, P.; Hanania, G. I. H.; Irvine, D. H.; Aber-Issu, J. Chem. Soc. 1964, 5689-5694.
107. (a) Johnson, C. R.; Shepherd, R. E.; Marr, B.; O'Donnell, S.; Dressick, W. J. Am. Chem. Soc. 1980, 102, 6227-6235.
108. (b) Hoq, M. F.; Shepherd, R. E. Inorg. Chem. 1984, 23, 1851-1858.
109. (c) Review: Sjoberg, S. Pure Appl. Chem. 1997, 69, 1549-1570.
110. Plass, W. Coord. Chem. Rev. 2003, 237, 205-212.