Density functional and MP2 studies of germylene insertion into C-H, Si-H, N-H, P-H, O-H, S-H, F-H, and Cl-H bonds

Journal of Physical Chemistry A

Volumn 103, Issue 50, 1999, Pages 11011-11019

  Su, Ming Der ^a   Chu, San Yan ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001394373     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp9916440     Document Type: Article

References (70)

1. For reviews, see: (a) Hine, J. Divalent Carbon; Academic Press: New York, 1964.
2. (b) Kirmse, W. Carbene Chemistry, 1st ed.; Academic Press: New York, 1964; Chapter 1.
3. (c) Bethell, D.Adu. Phys. Org. Chem. 1969, 7, 153-209.
4. (d) Moss, R. A. Selective Organic Transformations; Thyagarajan, B. S., Ed.; Wiley: New York, 1970; pp 35-88.
5. (e) Krimes, W. Carbene Chemistry, 2nd ed.; Academic Press: New York, 1971; Chapter 8.
6. (f) Moss, R. A.; Jones, M., Jr. Carbenes; Wiley: New York, 1973; Vol. 1.
7. (g) Jones, M., Jr.; Moss, R. A. Carbenes; Wiley: New York, 1975; Vol. 2.
8. (h) Moss, R. A.; Jones, M., Jr. Reactive Intermediates; Wiley: New York, 1978; Vol. 1.
9. (i) Moss, R. A.; Jones, M., Jr. Reactive Intermediates; Wiley: New York, 1981; Vol. 2, Chapter 3.
10. (j) Moss, R. A.; Jones, M., Jr. Reactive Intermediates; Wiley: New York, 1985; Vol. 3, Chapter 3.
11. (k) Abramovitch, R. A. Reactive Intermediates; Plenum: New York, 1980; Vol. 1.
12. (l) Platz, M. S. Kinetics and Spectroscopy of Carbenes and Biradicals, Plenum: New York, 1990.
13. (a) Baldridge, K. K.; Boatz, J. A.; Koseki, S.; Gordon, M. S. Annu. Rev. Phys. Chem. 1987, 38, 211.
14. (b) Apeloig, Y. The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1989.
15. (c) Jutzi, P. Frontiers of Organosilicon Chemistry; Bassindale, A. R., Caspar, P. P., Eds.; Royal Society of Chemistry: Cambridge, 1991.
16. (a) Lesbre, M.; Mazerroles, P.; Satge, J. The Organic Compounds of Germanium; Zinatne: Riga, 1990.
17. (b) Lukevics, E.; Gar, T.; Ignatovich, L.; Mironov, B. Biological Activity of Germanium; Zinatne: Riga, 1993.
18. (c) Lukevics, E.; Ignatovich, L. Frontiers of Organogennaniiim-Tin-Lead Chemistry; Latvian Institute: Riga, 1993.
19. (d) Patai, S. The Chemistry of Organic Germanium, Tin, and Lead Compounds; Wiley: 1995.
20. Stabilization of germylenes can be achieved by n-donor or p-donor substitueras, which reduce the electrophilicity of the germanium atom donating electrons into its vacant p-orbital, and by bulky substituents to prevent dimerization or oligomerization. See: Winter, J. G.; Portius, P.; Kociok-Kohn, G.; Steck, R.; Filippou, A. C. Organometallics 1998, 17, 4176, and references therein.
21. For theoretical investigations concerning the addition chemistry of germylene, see: Su, M.-D.; Chu, S.-Y. J. Am. Chem. Soc., in print.
22. Riviere, P.; Riviere-Baudet, M.; Satge, J. In Comprehensive Organometallic Chemistry; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K., 1995; Vol. 2, pp 193.
23. Neumann, W. P. Chem. Rev. 1991,91,311, and references therein.
24. (a) Su, M.-D.; Chu, S.-Y. J. Am. Chem. Soc. 1999,121, 4229.
25. (b) Su, M.-D.; Chu, S.-Y. Tetrahedron Lett. 1999, 40, 4371.
26. (a) Becke, A. D. Phys. Rev. A 1988, 38, 3098.
27. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
28. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
29. Ricca, A.; Bauschlicher, C. W. Ttieor. Chim. Acta 1995, 92, 123.
30. (a) Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650.
31. (b) Curtiss, L. A.; McGrath, M. P.; Blaudeau, J.-P.; Davis, N. E.; Binning, R. C.; Radom, L. J. Chem. Phys. 1995, 103, 6104.
32. Frisch, M. J.; Pople, J. A.; Binkley, J. S. J. Chem. Phys. 1984, 80, 3265.
33. Moller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618.
34. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Peterson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzevvski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A.; Gaussian 94; Gaussian, Inc.: Pittsburgh, PA, 1995.
35. (a) Cramer, C. J.; Dulles, F. J.; Storer, J. W.; Worthington, S. E. Chem. Phys. Lett. 1994, 218, 387.
36. (b) For the experimental evidence see: Kocher, J.; Lehnig, M. Organometallics 1984, 3, 937.
37. 2 see: Richards, C. A.; Kim, S.-J.; Yamaguchir Y.; Schaefer, H. F. III. J. Am. Chem. Soc. 1995, 117, 10104.
38. 2 see: Krogh-Jespersen, K. J. Ain. Chem. Soc. 1985, 707, 537.
39. 2 see: Shusterman, A. J.; Landrum, B. E.; Miller, R. L. Organometallics 1989, S, 1851.
40. Isaacs, N. S. Physical Organic Chemistry; Wiley: New York, 1995; p 199.
41. Barrau, J.; Bouchaut, M.; Lavayssieve, H.; Dousse, G.; Satge, J. J. Organomet. Chem. 1983, 243, 281.
42. (a) Withnall, R.; Andrews, L. J. Phys. Chem. 1990, 94, 2351.
43. (b) Nowek, A.; Leszczynski, J. /. Phys. Chem. A 1997, 707, 3784.
44. Ando, W.; Itoh, H.; Tsumuraya, T. Organometallics 1989, 8, 2759.
45. Hammond, G. S. J. Am. Chem. Soc. 1954, 77, 334.
46. (a) Lange, L.; Meyer, B.; DuMont, W.-W. J. Organomet. Chem. 1987, 529, C17. After this paper was submitted, four recent papers related germylene insertions into C-H bonds have been found:
47. (b) Jutzi, P.; Schmidt, H.; Neumann, B.; Stammler, H.-G., Organometallics, 1996, 75, 741.
48. (c) Lei, D.; Lee, M. E.; Caspar, P. P.; Tetrahedron, 1997, 53, 10179.
49. (d) Becerra, R.; Boganov, S. E.; Egorov, M. P.; Lee, V. Y.; Nefedov, O. M.; Walsh, R. Chem. Phys. Lett. 1996, 250, 111.
50. (e) Becerra, R.; Boganov, S. E.; Egorov, M. P.; Faustov, V. I.; Nefedov, O. M.; Walsh, R. J. Am. Chem. Soc. 1998, 720, 12657.
51. (a) Becerra, R.; Boganov, S. E.; Egorov, M. P.; Nefedov, O. M.; Walsh, R. Chem. Phys. Lett. 1996, 260, 433.
52. (b) Becerra, R.; Boganov, S. E.; Egorov, M. P.; Faustov, V. I.; Nefedov, O. M.; Walsh, R. J. Am. Chem. Soc. 1998, 120, 12657.
53. (a) Mochida, K.; Hasegawa, A. Chem. Lett. 1989, 1087.
54. (b) Baines, K. M.; Cooke, J. A. Organometallics 1992, 11, 3487.
55. (c) Baines, K. M.; Cooke, J. A.; Vittal, J. J. J. Chem. Soc., Chem. Commun. 1992, 1484.
56. Bach, R. D.; Andres, J. L.; Su, M.-D.; McDouall, J. J. W. J. Am. Chem. Soc. 1993, 115, 5768.
57. For instance, there are several possible mechanisms for the O-H insertion reaction of carbene. See: Krimse, W.; Meinen, T.; Modarelli, D. A.; Platz, M. S. J. Am. Chem. Soc. 1993, 115, 8918.
58. Raghavachari, K.; Chandrasekhar, J.; Gordon, M. S.; Dykenma, K. J. J. Am. Chem. Soc. 1984, 106, 5853.
59. (a) Gillette, G. R.; Noren, G. H.; West, R. Organometallics 1989, 8, 487.
60. (b) Ando, W.; Sekiguchi, A.; Hagiwara, K., Sakakibara, A.; Yoshida, H. Organometallics 1988, 7, 558.
61. Pettersson, L. G. M.; Schule, J. J. Mol. Struct. 1990, 205, 137.
62. (a) Shaik, S.; Schlegel, H. B.; Wolfe, S. Theoretical Aspects of Physical Organic Chemistry; John Wiley & Sons Inc.: New York, 1992.
63. (b) Pross, A. Theoretical and Physical Principles of Organic Reactivity, John Wiley & Sons Inc.: New York, 1995.
64. Su, M.-D. Inorg. Chem. 1995, 34, 3829.
65. Kerr, J. A. CRC Handbook of Chemistry and Physics, 75th ed.; West, R. C., Ed.; CRC: Boca Raton, NY, 1988.
66. n hydrides, in which the triplet state was calculated at B3LYP/6-311G* using the singlet geometry of the same level. For details see ref 33.
67. Su, M.-D.; Chu, S.-Y. Eur. J. Chem. 1999, 5, 198.
68. Similar steric arguments have been successful in explaining the trend in activation barriers for H-H, C-H, and C-C bond breaking reactions by transition metal complexes and can also be used to explain the lower barrier for the C-H bond breaking in various kinds of hydrocarbons. See: Siegbahn, P. E. M.; Blomberg, M. R. A. Theoretical Aspects of Homogeneous Catalysis; van Leeuwen, P. W. N. M., Morokuma, K., van Lenthe, J. H., Eds.; Kluwer Academic Publishers: Dordrecht, 1995, and references therein.
69. Riviere, P.; Riviere-Baudet, M.; Satge, J. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon: Oxford, U.K., 1982; Vol. 2, Chapter 10.
70. Minkin, V. I.; Simkiri, B. Y.; Glukhovtsev, M. N. Russ. Chem. Rev. 1989, 58, 622.