Symmetry and geometry considerations of atom transfer: Deoxygenation of (silox)3WNO and R3PO (R = Me, Ph, tBu) by (silox)3M (M = V, NbL (L = PMe3, 4-picoline), Ta; silox = tBu3SiO)

Inorganic Chemistry

Volumn 42, Issue 20, 2003, Pages 6204-6224

  Veige, Adam S ^a   Slaughter, LeGrande M ^a   Lobkovsky, Emil B ^a   Wolczanski, Peter T ^a   Matsunaga, Nikita ^b   Decker, Stephen A ^c   Cundari, Thomas R ^c  

^a Department of Obstetrics Gynecology   (United States)

^b LONG ISLAND UNIVERSITY   (United States)

^c UNIVERSITY OF NORTH TEXAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PICOLINE DERIVATIVE; SILICON DERIVATIVE; TUNGSTEN;

ARTICLE; ATOMIC PARTICLE; CHEMICAL BINDING; CHEMICAL STRUCTURE; CONCENTRATION (PARAMETERS); ELECTRONICS; ENERGY; ENZYME SUBSTRATE; GEOMETRY; OXYGENATION; STRUCTURE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0141566522     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic0300114     Document Type: Article

References (138)

1. (a) Shilov, A. E.; Shteinman, A. A. Acc. Chem. Res. 1999, 32, 763-771.
2. (b) Woo, L. K. Chem. Rev. 1993, 93, 1125-1136.
3. (c) Jorgensen, K. A. Chem. Rev. 1989, 89, 431-458.
4. (d) Holm, R. H. Coord. Chem. Rev. 1990, 100, 183-221.
5. (e) Holm, R. H. Chem. Rev. 1987, 87, 1401-1449.
6. (a) Cytochrome P450, Structure, Mechanism and Biochemistry, 2nd ed.; Ortiz de Montellano, P. R., Ed.; Plenum: New York, 1995.
7. (b) Enemark, J. H.; Young, C. G. Adv. Inorg. Chem. 1993, 40, 1-88.
8. (a) De Visser, S. P.; Ogliaro, F.; Sharma, P. K.; Shaik, S. J. Am. Chem. Soc 2002, 124, 11809-11826.
9. (b) Schoneboom, J. C.; Lin, H.; Reuter, N.; Thiel, W.; Cohen, S.; Ogliaro, F.; Shaik, S. J. Am. Chem. Soc. 2002, 124, 8142-8151.
10. (c) de Visser, S. P.; Ogliaro, F.; Sharma, P. K. Shaik, S. Angew. Chem., Int. Ed. 2002, 41, 1947-1950.
11. (d) de Visser, S. P.; Ogliaro, F.; Harris, N.; Shaik, S. J. Am. Chem. Soc. 2001, 123, 3037-3047.
12. (e) Ogliaro, F.; Harris, N.; Cohen, S.; Filatov, M.; de Visser, S. P.; Shaik, S. J. Am. Chem. Soc. 2000, 122, 8977-8989.
13. (a) Hille, R. Chem. Rev. 1996, 96, 2757-2816.
14. (b) McMaster, J.; Enemark, J. H. Curr. Opin. Chem. Biol. 1998, 2, 201-207.
15. (c) Romao, M. J.; Huber, R. Struct. Bonding 1998, 90, 69-95.
16. (a) Lim, B. S.; Holm, R. H. J. Am. Chem. Soc. 2001, 123, 1920-1930.
17. (b) Sung, K. M.; Holm, R. H. J. Am. Chem. Soc. 2001, 123, 1931-1943.
18. (a) Pietsch, M. A.; Hall, M. B. Inorg. Chem. 1996, 35, 1273-1278.
19. (b) Pietsch, M. A.; Couty, M.; Hall, M. B. J. Phys. Chem. 1995, 99, 16315-16319.
20. Thomson, L. M.; Hall, M. B. J. Am. Chem. Soc. 2001, 123, 3995-4002.
21. (a) Jin, N.; Groves, J. T. J. Am. Chem. Soc. 1999, 121, 2923-2924.
22. (b) Groves, J. T.; Lee, J.; Marla, S. S. J. Am. Chem. Soc. 1997, 119, 6269-6273.
23. Jin, N.; Bourassa, J. L.; Tizio, S. C.; Groves, J. T. Angew. Chem., Int. Ed. 2000, 39, 3849-3851.
24. (a) Butler, A. Coord. Chem. Rev. 1999, 187, 17-35.
25. (b) Butler, A.; Baldwin, A. H. Struct. Bonding 1997, 89, 109-132.
26. (a) Merkx, M.; Kopp, D. A.; Sazinsky, M. H.; Blazyk, J. L.; Müller, J.; Lippard, S. J. Angew. Chem., Int. Ed. 2001, 40, 2782-2807.
27. (b) Wallar, B. J.; Lipscomb, J. D. Chem. Rev. 1996, 96, 2625-2657.
28. (c) Que, L.; Tolman, W. B. Angew. Chem., Int. Ed. 2002, 41, 1114-1137.
29. Ambundo, E. A.; Friesner, R. A.; Lippard, S. J. J. Am. Chem. Soc. 2002, 124, 8770-8771.
30. Brazeau, B. J.; Austin, R. N.; Tarr, C.; Groves, J. T.; Lipscomb, J. D. J. Am. Chem. Soc. 2001, 123, 11831-11837.
31. Costas, M.; Rohde, J. U.; Stubna, A.; Ho, R. Y. N.; Quaroni, L.; Munck, E.; Que, L. J. Am. Chem. Soc. 2001, 123, 12931-12932.
32. (a) Palucki, M.; Finney, N. S.; Pospisil, P. J.; Güler, M. L.; Ishida, T.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 948-954.
33. (b) Finney, N. S.; Pospisil, P. J.; Chang, S.; Palucki, M.; Konsler, R. G.; Hansen, K. B.; Jacobsen, E. N. Angew. Chem., Int. Ed. Engl. 1997, 36, 1720-1723.
34. Katsuki, T. Coord. Chem. Rev. 1995, 140, 189-214.
35. (a) Cavallo, L.; Jacobsen, H. Chem. Eur. J. 2001, 7, 800-807.
36. (b) Cavallo, L.; Jacobsen, H. Angew. Chem., Int. Ed. 2000, 39, 589-592.
37. (c) Linde, C.; Åkermark, B.; Norrby, P.-O.; Svensson, M. J. Am. Chem. Soc. 1999, 121, 5083-5084.
38. (d) Linde, C.; Arnold, M.; Norrby, P.-O.; Åkermark, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1723-1725.
39. (a) Kolb, H. C.; VanNieuwenzhe, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547.
40. (b) Andersson, M. A.; Epple, R.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 472-475.
41. (a) DelMonte, A. J.; Haller, J.; Houk, K. N.; Sharpless, K. B.; Singleton, D. A.; Strassner, T.; Thomas, A. A. J. Am. Chem. Soc. 1997, 119, 9907-9908.
42. (b) Norrby, P.-O.; Rasmussen, T.; Haller, J.; Strassner, T.; Houk, K. N. J. Am. Chem. Soc. 1999, 121, 10186-10192.
43. Corey, E. J.; Noe, M. C. J. Am. Chem. Soc. 1996, 118, 11038-11053.
44. (a) Chen, K.; Costas, M.; Kim, J. H.; Tipton, A. K.; Que, L. J. Am. Chem. Soc. 2002, 124, 3026-3035.
45. (b) Chen, K.; Costas, M.; Que, L. J. Chem. Soc., Dalton Trans. 2002, 672-679.
46. (c) Costas, M.; Que, L. Angew. Chem., Int. Ed. 2002, 41, 2179-2181.
47. (d) Ryu, J. K.; Kim, J.; Costas, M.; Chen, K.; Nam, W.; Que, L. Chem. Commun. 2002, 1288-1289.
48. White, M. C.; Doyle, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 7194-7195.
49. (a) Ruiz, J.; Vivanco, M.; Floriani, C.; Chiesi-Villa, A.; Guastini, C. J. Chem. Soc., Chem. Commun. 1991, 762-764.
50. (b) Vivanco, M.; Ruiz, J.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Organometallics 1993, 12, 1802-1810.
51. Odom, A. L.; Cummins, C. C.; Protasiewicz, J. D. J. Am. Chem. Soc. 1995, 117, 6613-6614.
52. (a) Crevier, T. J.; Mayer, J. M. J. Am. Chem. Soc. 1997, 119, 8485-8491.
53. (b) Hall, K. A.; Mayer, J. M. J. Am. Chem. Soc. 1992, 114, 10402-10411.
54. Sung, K.-M.; Holm, R. H. Inorg. Chem. 2001, 40, 4518-4525.
55. (a) Parshall, G. W.; Ittel, S. D. Homogeneous Catalysis; Wiley-Interscience: New York, 1992.
56. (b) Sheldon, R. A.; Kochi, J. K. Metal Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1981.
57. 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.
58. Veige, A. S.; Kleckley, T. S.; Chamberlin, R. L. M.; Neithamer, D. R.; Lee, C. E.; Wolczanski, P. T.; Lobkovsky, E. B.; Glassey, W. V. J. Organomet. Chem. 1999, 591, 194-203.
59. 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.
60. Bonanno, J. B.; Henry, T. P.; Neithamer, D. R.; Wolczanski, P. T.; Lobkovsky, E. B. J. Am. Chem. Soc. 1996, 118, 5132-5133.
61. Hess, J. S.; Leelasubcharoen, S.; Rheingold, A. L.; Doren, D. J.; Theopold, K. H. J. Chem. Soc. 2002, 124, 2454-2455.
62. Pistorio, B. J.; Chang, C. J.; Nocera, D. G. J. Chem. Soc. 2002, 124, 7884-7885.
63. (a) Poli, R. Chem. Rev. 1996, 96, 2135-2204.
64. (b) Poli, R. Acc. Chem. Res. 1997, 30, 494-501.
65. Poli, R.; Harvey, J. N. Chem. Soc. Rev. 2003, 32, 1-8.
66. Alyea, E. C.; Bradley, D. C.; Copperthwaite, R. G. J. Chem. Soc., Dalton Trans. 1972, 1580-1584.
67. (a) Evans, D. F. J. Chem. Soc. 1959, 2003-2005.
68. (b) Orrell, K. G.; Sik, V. Anal. Chem. 1980, 52, 567-569.
69. (c) Schubert, E. M. J. Chem. Educ. 1992, 69, 62.
70. Drago, R. S. Physical Methods for Chemists; Saunders: New York, 1992.
71. Neithamer, D. R. Ph.D. Thesis, Cornell University, 1989.
72. (a) Henderson, R. A.; Janas, Z.; Jerzykiewicz, L. B.; Richards, R. L.; Sobota, P. Inorg. Chim. Acta 1999, 285, 178-183.
73. (b) Henderson, R. A.; Hughes, D. L.; Janas, Z.; Richards, R. L.; Sobota, P.; Szafert, S. J. Organomet. Chem. 1998, 554, 195-201.
74. (c) Scott, M. J.; Wilisch, W. C. A.; Armstrong, W. H. J. Am. Chem. Soc. 1990, 112 2429-2430.
75. (d) Wilisch, W. C. A.; Scott, M. J.; Armstrong, W. H. Inorg. Chem. 1988, 27, 4333-4335.
76. (e) Carrano, C. J.; Mohan, M.; Holmes, S. M.; de la Rosa, R.; Butler, A. ; Charnock, J. M.; Garner, C. D. Inorg. Chem. 1994, 33, 646-655.
77. Tayebani, M.; Conoci, S.; Feghali, K.; Gambarotta, S.; Yap, G. P. A. Organometallics 2000, 19, 4568-4574.
78. (a) Caselli, A.; Solari, E.; Scopelliti, R.; Floriani, C.; Re, N.; Rizzoli, C.; Chiesi-Villa, A. J. Am. Chem. Soc. 2000, 122, 3652-3670.
79. (b) Kawaguchi, H.; Matsuo, T. Angew. Chem., Int. Ed. 2002, 41, 2792-2794.
80. 3WCl (6, highly dist sq pl)) and chemistry of silox tungsten chlorides, see: (a) Majol, A.-R. Ph.D. Thesis, Cornell University, 1999.
81. (b) Chamberlin, R. L.; Douthwaite, R. E.; Majol A.-R.; Slaughter, L. M.; Veige, A. S.; Wolczanski, P. T. Manuscript in preparation.
82. -1 significant coupling with the axial Cl or the oxygens was not noted.
83. Parkin, G.; Bercaw, J. E. Polyhedron 1988, 7, 2053-2082.
84. Nugent, W. A.; Mayer, J. M., Metal-Ligand Multiple Bonds; John Wiley & Sons: New York, 1988.
85. Hayton, T. W.; Legzdins, P.; Sharp, W. B. Chem. Rev. 2002, 102, 935-991.
86. (a) Legzdins, P.; Rettig, S. J.; Ross, K. J.; Weltheer, J. E. J. Am. Chem. Soc. 1991, 113, 4361-4363.
87. (b) Brouwer, E. B.; Legzdins, P.; Rettig, S. J.; Ross, K. J. Organometallics 1994, 13, 2088-2091.
88. (c) Debad, J. D.; Legzdins, P.; Reina, R.; Young, M. A.; Batchelor, R. J.; Einstein, F. W. B. Organometallics 1994, 13, 4315-4321.
89. Mindiola, D. J.; Cummins, C. C. Angew Chem., Int. Ed. 1998, 37, 945-947.
90. Parkin, G. Acc. Chem. Res. 1992, 25, 455-460.
91. (a) Chisholm, M. H.; Hoffman, D. M.; Huffman, J. C. Inorg. Chem. 1983, 22, 2903-2906.
92. (b) Chisholm, M. H.; Folting, K.; Lynn, M. L.; Tiedtke, D. B.; Lemoigno, F.; Eisenstein, O. Chem. Eur. J. 1999, 5, 2318-2326.
93. (c) Pollagi, T. P.; Stoner, T. C.; Dallinger, R. F.; Gilbert, T. M.; Hopkins, M. D. J. Am. Chem. Soc. 1991, 113, 703-704.
94. Holm, R. H.; Donahue, J. P. Polyhedron 1993, 12, 571-593.
95. Covert, K. J.; Neithamer, D. R.; Zonnevylle, M. C.; LaPointe, R. E.; Schaller, C. P.; Wolczanski, P. T. Inorg. Chem. 1991, 30, 2494-2508.
96. (a) Kleckley, T. S.; Bennett, J. L.; Wolczanski, P. T.; Lobkovsky, E. B. J. Am. Chem. Soc. 1997, 119, 247-248.
97. (b) Kleckley, T. S. Ph.D. Thesis, Cornell University, 1998.
98. Miller, R. L.; Toreki, R.; LaPointe, R. E.; Wolczanski, P. T.; Van Duyne, G. D.; Roe, D. C. J. Am. Chem. Soc. 1993, 115, 5570-5588.
99. Similar intermediates have recently been identified in transferases: Smith, P. D.; Millar, A. J.; Young, C. G.; Ghosh, A.; Basu, P. J. Am. Chem. Soc. 2000, 122, 9298-9299.
100. (a) Espensen, J. H.; Shan, X.; Wang, Y.; Huang, R.; Lahti, D. W.; Dixon, J.; Lente, G.; Ellern, A.; Guzei, I. A. Inorg. Chem. 2002, 41, 2583-2591.
101. (b) Wang, Y.; Lente, G.; Espensen, J. H.; Guzei, I. A. Inorg. Chem. 2002, 41, 1272-1280.
102. Nemyin, v. N.; Divie, S. R.; Mondal, S.; Rubie, N.; Kirk, M. L.; Somogyi, A.; Basu, P. J. Am. Chem. Soc. 2002, 124, 756-757.
103. (a) Gangopadhyay, J.; Sengupta, S.; Bhattacharyya, S.; Chakraborty, I.; Chakravorty, A. Inorg. Chem. 2002, 41, 2616-2622.
104. (b) Bhattacharyya, S.; Chakraborty, I.; Dirghangi, B. K. Inorg. Chem. 2001, 40, 286-293.
105. Arias, J.; Newlands, C. R.; Abu-Omar, M. M. Inorg. Chem. 2001, 40, 2185-2192.
106. Stevens, W. J.; Krauss, M.; Basch, H.; Jasien, P. G. Can. J. Chem. 1992, 70, 612-630.
107. Benson, M. T.; Cundari, T. R.; Lutz, M. L.; Sommerer, S. O. In Reviews in Computational Chemistry; Boyd, D., Lipkowitz, K., Eds.; Wiley: New York, 1996; Vol. 8, p 145.
108. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
109. Bartlett, R. J.; Stanton, J. F. In Reviews in Computational Chemistry; Boyd, D. B., Lipkowitz, K. B., Eds.; Wiley: New York, 1994; Vol. 5, pp 65-169.
110. Frenking, G.; Antes, I.; Bohme, M.; Dapprich, S.; Ehlers, A. W.; Jonas, V.; Neuhaus, A.; Otto, M.; Stegmann, R.; Veldkamp, A.; Vyboishchikov, S. F. In Reviews in Computational Chemistry; Boyd, D., Lipkowitz, K., Eds.; Wiley: New York, 1996; Vol. 8, pp 63-144.
111. 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, Inc.; Pittsburgh, PA, 1998.
112. Veige, A. S.; Wolczanski, P. T.; Lobkovsky, E. B. Chem. Commun. 2001, 2734-2735.
113. (a) Tolman, C. A. Chem. Rev. 1977, 77, 313-348.
114. (b) Bunten, K. A.; Chen, L.; Fernandez, A. L.; Poë, A. J. Coord. Chem. Rev. 2002, 233-234, 41-51.
115. (a) Lappin, A. G. Redox Mechanisms in Inorganic Chemistry; Ellis Horwood: New York, 1994.
116. (b) Tobe, M. L.; Burgess, J. Inorganic Reaction Mechanisms; Addison-Wesley Longman: New York, 1999.
117. RHF = restricted Hartree-Fock; ROHF = restricted open-shell 1 Hartree-Fock. Young, D. In Computational Chemistry; Wiley: New York, 2001; pp 20, 227-229.
118. Wolczanski, P. T. Polyhedron 1995, 14, 3335-3362.
119. Oxtoby, D. W.; Gillis, H. P.; Nachtrieb, N. H. Principles of Modern Chemistry, 5th ed.; Thomson Brooks/Cole: U.S.A., 2002; p 552.
120. 3 (1′-M, M = V, Nb, Ta).
121. (a) Harvey, J. N. In Spin Forbidden Reactions in Transition Metal Chemistry; Cundari, T. R., Ed.; Marcel Dekker: Basel, 2001.
122. (b) Harvey, J. N. J. Am. Chem. Soc. 2000, 122, 12401-12402 and references therein.
123. Extended Hückel molecular orbital (EHMO) calculations were conducted using the HyperChem program: HyperChem(TM), Hypercube, Inc., 1115 NW 4th St., Gainesville, FL 32601.
124. Woo, L. K.; Goll, J. G.; Berreau, L. M.; Weaving, R. J. Am. Chem. Soc. 1992, 114, 7411-7415.
125. Tatsumi, K.; Hoffmann, R. J. Am. Chem. Soc. 1981, 103, 3328-3341.
126. Detrich, J. L.; Reinaud, O. M.; Rheingold, A. L.; Theopold, K. H. J. Am. Chem. Soc. 1995, 117, 11745-11748.
127. Brock, S. L.; Mayer, J. M. Inorg. Chem. 1991, 30, 2138-2143.
128. Laplaza, C. E.; Johnson, M. J. A.; Peters, J. C.; Odom, A. L.; Kim, E.; Cummins, C. C.; George, G. N.; Pickering, I. J. J. Am. Chem. Soc. 1996, 118, 8623-8638.
129. Cherry, J.-P. F.; Johnson, A. R.; Baraldo, L. M.; Tsai, Y.-C.; Cummins, C. C.; Kryatov, S. V.; Rybak-Akimova, E. V.; Capps, K. B.; Hoff, C. D.; Haar, C. M.; Nolan, S. P.J. Am. Chem. Soc. 2001, 123, 7271-7286.
130. Seymore, S. B.; Brown, S. N. Inorg. Chem. 2002, 41, 462-469.
131. Ware, D. C.; Taube, H. Inorg. Chem. 1991, 30, 4605-4610.
132. Shin, J. H.; Bridgewater, B. M.; Churchill, D. G.; Baik, M.-H.; Friesner, R. A.; Parkin, G. J. Am. Chem. Soc. 2001, 123, 10111-10112.
133. Smith, K. M.; Poli, R.; Legzdins, P. Chem. Eur. J. 1999, 5, 1598-1608.
134. Smith, K. M.; Poli, R.; Harvey, J. N. New J. Chem. 2000, 24, 77-80.
135. Franke, O.; Wiesler, B. E.; Lehnert, N.; Näther, C.; Ksenofontov, V.; Neuhausen, J.; Tuczek, F. Inorg. Chem. 2002, 41, 3491-3499.
136. (a) Smith, K. M.; Poli, R.; Harvey, J. N. Chem. Eur. J. 2001, 7, 1679-1690.
137. (b) Green, J. C.; Harvey, J. N.; Poli, R. J. Chem. Soc., Dalton Trans. 2002, 1861-1866.
138. International Tables for Crystallography: Wilson, A. J. C., Ed.; Kluwer Academic Publishers: Boston, 1995; Vol. C, p 13, Table 1.3.4.2.