Do B3LYP and CCSD(T) predict different hydrosilylation mechanisms? Influences of theoretical methods and basis sets on relative energies in ruthenium-silylene-catalyzed ethylene hydrosilylation

Journal of Physical Chemistry A

Volumn 110, Issue 4, 2006, Pages 1416-1425

  Beddie, Chad ^a   Hall, Michael B ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DENSITY FUNCTIONAL THEORY (DFT); POTENTIAL REACTION PATHWAYS; WAVE FUNCTION THEORY (WFT);

CATALYSIS; COMPUTATIONAL METHODS; ETHYLENE; REACTION KINETICS;

RUTHENIUM;

EID: 32544435319     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp054622o     Document Type: Article

References (87)

1. Tilley, T. D. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons Ltd.: New York, 1989; pp 1415-1477.
2. Ojima, I. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons Ltd.: New York, 1989; pp 1479-1526.
3. Marciniec, B. Appl. Organomet. Chem. 2000, 14, 527-538.
4. Marciniec, B. Silicon Chem. 2002, 1, 155-175.
5. Carpentier, J.-F.; Bette, V. Curr. Org. Chem. 2002, 6, 913-936.
6. Glaser, P. B.; Tilley, T. D. J. Am. Chem. Soc. 2003, 125, 13640-13641.
7. For example, in the Chalk-Harrod mechanism, olefin inserts into the metal-hydrogen bond ((a) Chalk, A. J.; Harrod, J. F. J. Am. Chem. Soc. 1965, 87, 16-21.
8. (b) Chalk, A. J.; Harrod, J. F. J. Am. Chem. Soc. 1965, 87, 1133-1135.),
9. whereas, in the modified Chalk-Harrod mechanism proposed by Sietz and Wrighton, olefin inserts into the metal-silicon bond ((c) Seitz, F.; Wrighton, M. S. Angew. Chem., Int. Ed. Engl. 1988, 27, 289-291.
10. (d) Duckett, S. B.; Perutz, R. N. Organometallics 1992, 11, 90-98.).
11. 0 metals also occur within the first coordination sphere of the transition metal ((e) Corey, J. Y.; Zhu, X.-H. Organometallics 1992, 11, 672-683.
12. (f) Kesti, M. R.; Waymouth, R. M. Organometallics 1992, 11, 1095-1103.).
13. For theoretical investigations on other hydrosilylation catalysts, see (a) Sakaki, S.; Takayama, T.; Sumimoto, M.; Sugimoto, M. J. Am. Chem. Soc. 2004, 126, 3332-3348.
14. (b) Chung, L. A.; Wu, Y.; Trost, B. M.; Ball, Z. T. J. Am. Chem. Soc. 2003, 125, 11578-11582.
15. (c) Sakaki, S.; Sumimoto, M.; Fukuhara, M.; Sugimoto, M.; Fujimoto, H.; Matsuzaki, S. Organometallics 2002, 21, 3788-3802 and references therein.
16. Brunner, H. Angew. Chem., Int. Ed. 2004, 43, 2749-2750.
17. Beddie, C.; Hall, M. B. J. Am. Chem. Soc. 2004, 126, 13564-13565.
18. Fan, Y.; Hall, M. B. Chem.-Eur. J. 2004, 10, 1805-1814.
19. Hall, M. B.; Fan, H.-I. Adv. Inorg. Chem. 2003, 54, 321-349.
20. Niu, S.; Hall, M. B. Chem. Rev. 2000, 100, 353-405.
21. (a) Cizek, J. Adv. Chem. Phys. 1969, 14, 35-89.
22. (b) Purvis, G. D.; Bartlett, R. J. J. Chem. Phys. 1982, 76, 1910-1918.
23. (c) Scuseria, G. E. Janssen, C. L.; Schaefer, H. F., III J. Chem. Phys. 1988, 89, 7382-7387.
24. (d) Scuseria, G. E.; Schaefer, H. F., III J. Chem. Phys. 1989, 90, 3700-3703.
25. (a) Raghavachari, K.; Trucks, G. W.; Pople, J. A.; Head-Gordon, M. Chem. Phys. Lett. 1989, 157, 479-483.
26. (b) Pople, J. A.; Gordon-Head, M.; Raghavachari, K. J. Chem. Phys. 1987, 87, 5968-5975.
27. (c) Watts, J. D.; Gauss, J.; Barlett, R. J. J. Chem. Phys. 1998, 98, 8718-8733.
28. Preliminary results were initially reported as Beddie, C.; Hall, M. B. Abstracts of Papers, 229th ACS National Meeting, San Diego, CA, March 13-17, 2005; American Chemical Society: Washington, DC, 2005.
29. All calculations were conducted using the Gaussian03 suite of programs: 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. Gaussian03, revision B.4; Gaussian, Inc.: Pittsburgh, PA, 2003.
30. Becke, A. D. J. Chem. Phys. 1993, 95, 5648-5652.
31. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
32. Couty, M.; Hall, M. B. J. Comput. Chem. 1996, 17, 1359-1370.
33. (a) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270-283.
34. (b) Wadt, W. R.; Hay, P. J. J. Chem. Phys. 1985, 82, 284-298.
35. (c) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299-310.
36. Ehlers, A. W.; Böhme, M.; Dapprich, S.; Gobbi, A.; Höllwarth, A.; Jonas, V.; Köhler, K. F.; Stegmann, R.; Veldkamp, A.; Frenking, G. Chem. Phys. Lett. 1993, 208, 111-114.
37. Andrae, D.; Haeussermann, U.; Dolg, M.; Stell, H.; Preuss, H. Theor. Chim. Acta 1990, 77, 123-141.
38. Basis sets were obtained from the Extensible Computational Chemistry Environment Basis Set Database, version 02/25/04, as developed and distributed by the Molecular Science Computing Facility, Environmental and Molecular Sciences Laboratory, which is part of the Pacific Northwest Laboratory, P.O. Box 999, Richland, WA 99352, USA, and funded by the U.S. Department of Energy. The Pacific Northwest Laboratory is a multiprogram laboratory operated by Battelle Memorial Institute for the U.S. Department of Energy under contract DE-AC06-76RLO 1830. Contact Karen Schuchardt for further information.
39. Check, C. E.; Faust, T. O.; Bailey, J. M.; Wright, B. J.; Gilbert, T. M.; Sunderlin, L. S. J. Phys. Chem. A 2001, 105, 8111-8116.
40. Woon, D. E.; Dunning, T. H., Jr. J. Chem. Phys. 1993, 98, 1358-1371.
41. Dunning, T. H., Jr. J. Chem. Phys. 1989, 90, 1007-1023.
42. Ditchfield, R.; Hehre, W. J.; Pople, J. A. J. Chem. Phys. 1971, 54, 724-728.
43. Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257-2261.
44. Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213-222.
45. Petersson, G. A.; Al-Laham, M. A. J. Chem. Phys. 1991, 94, 6081-6090.
46. Petersson, G. A.; Bennett, A.; Tensfeldt, T. G.; Al-Laham, M. A.; Shirley, W. A.; Mantzaris, J. J. Chem. Phys. 1988, 89, 2193-2218.
47. Foresman, J. B.; Frisch, M. Exploring Chemistry with Electronic Structure Methods, 2nd ed.; Gaussian, Inc.: Pittsburgh, PA, 1996; p 110. The 6-31G(d′) basis set has the d polarization functions for C, N, O, and F taken from the 6-311G basis set, instead of the original arbitrarily assigned value of 0.8 used in the 6-31G(d) basis set.
48. Clark, T.; Chandrasekhar, J.; Spitznagel, G. W.; Schleyer, P. v. R. J. Comput. Chem. 1983, 4, 294-301.
49. (a) Burke, K.; Perdew, J. P.; Wang, Y. In Electronic Density Functional Theory: Recent Progress and New Directions; Dobson, J. F., Vignale, G., Das, M. P., Eds.; Plenum: New York, 1998; pp 81-111.
50. (b) Perdew, J. P. In Electronic Structure of Solids '91; Ziesche, P., Eschrig, H., Eds.; Akademie Verlag: Berlin, 1991; p 11.
51. (c) Perdew, J. P.; Chevary, J. A.; Vosko, S. H.; Jackson, K. A.; Pederson, M. R.; Singh, D. J.; Fiolhais, C. Phys. Rev. B 1992, 46, 6671-6687.
52. (d) Perdew, J. P.; Chevary, J. A.; Vosko, S. H.; Jackson, K. A.; Pederson, M. R.; Singh, D. J.; Fiolhais, C. Phys. Rev. B 1993, 48, 4978.
53. (e) Perdew, J. P.; Burke, K.; Wang, Y. Phys. Rev. B 1996, 54, 16533-16539.
54. Adamo, C.; Barone, V. J. Chem. Phys. 1998, 108, 664-675.
55. Handy, N. C.; Cohen, A. J. Mol. Phys. 2001, 99, 403-412.
56. Cohen, A. J.; Handy, N. C. Mol Phys. 2001, 99, 607-615.
57. (a) Perdew, J. P.; Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1996, 77, 3865-3868.
58. (b) Perdew, J. P.; Burke, K.; Emzerhof, M. Phys. Rev. Lett. 1997, 78, 1396.
59. (a) Roothan, C. C. J. Rev. Mod. Phys. 1951, 23, 69-89.
60. (b) Pople, J. A. J. Chem. Phys. 1954, 22, 571-572.
61. (c) McWeeny, R.; Diercksen, G. J. Chem. Phys. 1968, 49, 4852-4856.
62. Moller, C.; Plessett, M. S. Phys. Rev. 1934, 46, 618-622.
63. (a) Head-Gordon, M.; Pople, J. A.; Frisch, M. J. Chem. Phys. Lett. 1988, 153, 503-506.
64. (b) Frisch, M. J.; Head-Gordon, M.; Pople, J. A. Chem. Phys. Lett. 1990, 166, 275-280.
65. (c) Frisch, M. J.; Head-Gordon, M.; Pople, J. A. Chem. Phys. Lett. 1990, 166, 281-289.
66. (d) Head-Gordon, M.; Head-Gordon, T. Chem. Phys. Lett. 1994, 220, 122-128.
67. (e) Saebo, S.; Almlof, J. Chem. Phys. Lett. 1989, 154, 83-89.
68. Pople, J. A.; Binkley, J. S.; Seeger, R. Int. J. Quantum Chem. Symp. 1976, 10, 1-19.
69. Pople, J. A.; Seeger, R.; Krishnan, R. Int. J. Quantum Chem. Symp. 1977, 11, 149-163.
70. Krishnan, R.; Pople, J. A. Int. J. Quantum Chem. 1978, 14, 91-100.
71. (a) Krishnan, R.; Schlegel, H. B.; Pople, J. A. J. Chem. Phys. 1980, 72, 4654-4655.
72. (b) Raghavachari, K.; Pople, J. A. Int. J. Quantum Chem. 1981, 20, 1067-1071.
73. Manson, J.; Webster, C. E.; Hall, M. B. JIMP Development, version 0.1 (built for Windows PC and Redhat Linux 7.3); Department of Chemistry, Texas A&M University: College Station, TX, 2004. http://www.chem.tamu.edu/jimp/.
74. Simon, S.; Duran, M.; Dannenberg, J. J. J. Chem. Phys. 1996, 105, 11024-11031.
75. Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553-566.
76. Hyla-Kryspin, I.; Grimme, S. Organometallics, 2004, 23, 5581-5592.
77. Torrent, M.; Solà, M.; Frenking, G. Chem. Rev. 2000, 100, 439-493.
78. Pople, J. A.; Head-Gordon, M.; Fox, D. J.; Raghavachari, K.; Curtiss, L. A. J. Chem. Phys. 1989, 90, 5622-5629.
79. Curtiss, L. A.; Jones, C.; Trucks, G. W.; Raghavachari, K.; Pople, J. A. J. Chem. Phys. 1990, 93, 2537-2545.
80. Curtiss, L. A.; Raghavachari, K.; Trucks, G. W.; Pople, J. A. J. Chem. Phys. 1991, 94, 7221-7230.
81. Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Rassolov, V.; Pople, J. A. J. Chem. Phys. 1998, 109, 7764-7776.
82. Zhao, Y.; Truhlar, D. G. J. Phys. Chem. A 2005, 109, 4209-4212.
83. Cramer, C. J. Essentials of Computational Chemistry, 2nd ed; John Wiley & Sons, Ltd.: West Sussex, England, 2004; pp 165-248.
84. Parthiban, S.; Martin, J. M. L. J. Chem. Phys. 2001, 114, 6014-6029.
85. Helgaker, T.; Klopper, W.; Halkier, A.; Bak, K. L.; Jørgenson, P.; Olsen, J. In Quantum Mechanical Prediction of Thermodynamic Data; Cioslowski, J., Ed.; Understanding Chemical Reactivity; Kluwer: Dordrecht, 2001; Vol. 22, pp 1-30.
86. Lee, T. J.; Taylor, P. R. Int. J. Quantum Chem. Symp. 1989, 23, 199-207.
87. BS7 is not a complete basis set extrapolation because both BS5 and BS6 use the same Ru basis set, namely, the Stuttgart 1997 ECP + f. To generate a complete basis set extrapolation of extremely high accuracy, cc-pVTZ and cc-pVQZ or aug-cc-pVTZ and aug-cc-pVQZ basis sets on all atoms would be preferred; however, calculations with these basis sets are beyond our computational resources.