Theoretical investigations of the reactivities of cationic six-membered carbene analogues of group 14 elements

Journal of Physical Chemistry A

Volumn 112, Issue 33, 2008, Pages 7689-7698

  Wang, Ren Hong ^a   Su, Ming Der ^a  

^a NATIONAL CHIAYI UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; GRAFTING (CHEMICAL); POTENTIAL ENERGY; POTENTIAL ENERGY SURFACES; PROBABILITY DENSITY FUNCTION; QUANTUM CHEMISTRY; SURFACE REACTIONS; SYNTHESIS (CHEMICAL);

B3LYP/LANL2DZ; CARBENE;

DENSITY FUNCTIONAL THEORY;

EID: 51049117063     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp8026397     Document Type: Article

References (50)

1. For recent reviews, see: (a) Barrau, J.; Escudié, J.; Satgé, J. Chem. Rev. 1990, 90, 283.
2. (b) Weidenbruch, M. Eur. J. Inorg. Chem. 1999, 373.
3. (c) 1c.
4. (d) Kühl, O. Coord. Chem. Rev. 2004, 248, 411.
5. (a) Arduengo III, A. J.; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 775, 361.
6. (b) Arduengo III, A. J.; Dias, H. V. R.; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1992, 114, 5530.
7. (c) Arduengo III, A. J.; Goerlich, J. R.; Marshall, W. J. J. Am. Chem. Soc. 1995, 177, 11027.
8. (d) Alder, R. W.; Allen, P. R.; Murray, M.; Orpen, A. G. Angew. Chem., Int. Ed. Engl. 1996, 35, 1121.
9. (e) Arduengo III, A. J.; Goerlich, J. R.; Marshall, W. J. Liebigs Ann. Reel. 1997, 365.
10. (f) Alder, R. W.; Butts, C. P.; Orpen, A. G. J. Am. Chem. Soc. 1998, 120, 11526.
11. (g) Liu, Y.; Lindner, P. E.; Lemal, D. M. J. Am. Chem. Soc. 1999, 121, 10626.
12. (h) Hahn, F. H.; Wittenbecher, L.; Le Van, D.; Fröhlich, R. Angew. Chem., Int. Ed. 2000, 39, 541.
13. (i) Heinemann, C.; Müller, T.; Apeloig, Y.; Schwarz, H. J. Am. Chem. Soc. 1996, 118, 2023.
14. (j) Boehme, C.; Frenking, G. J. Am. Chem. Soc. 1996, 118, 2039.
15. (k) Alder, R. W.; Blake, M. E.; Bortolotti, C.; Bufali, S.; Butts, C. P.; Linehan, E.; Oliva, J. M.; Orpen, A. G.; Quayle, M. J. Chem. Commun. 1999, 241.
16. (l) Guillen, F.; Winn, C. L.; Alexakis, A. Tetrahedron: Asymmetry 2001, 72, 2083.
17. (a) Driess, M.; Yao, S.; Brym, M.; Wüllen, C. V. Angew. Chem., Int. Ed. 2006, 45, 4349.
18. (b) Driess, M.; Yao, S.; Brym, M.; Wüllen, C. V. Angew. Chem., Int. Ed. 2006, 45, 6730.
19. (c) Yao, S.; Brym, M.; Wüllen, C. van.; Driess, M. Angew. Chem., Int. Ed. 2007, 46, 4159.
20. (d) Yao, S.; Wüllen, C. van.; Sun, X.-Y.; Driess, M. Angew. Chem., Int. Ed. 2008, 47, 3250.
21. (a) Ding, M.; Ma, Q.; Roesky, H. W.; Herbst-Irmer, R.; Usóm, I.; Noltemeyer, M.; Schmidt, H.-G. Organometallics 2002, 21, 5216.
22. (b) Driess, M.; Yao, S.; Brym, M.; Wüllen, C. V.; Lentz, D. J. Am. Chem. Soc. 2006, 128, 9628.
23. (c) Xiong, Y.; Yao, S.; Brym, M.; Driess, M. Angew. Chem., Int. Ed. 2007, 46, 4511.
24. (a) Becke, A. D. Phys. Rev. A 1988, 38, 3098.
25. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
26. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B, 1988, 37, 785.
27. (a) Dunning, T. H., Jr.; Hay, P. J. In Modern Theoretical Chemistry, Schaefer, H. F., III, Ed.; Plenum: New York, 1976; p1-28.
28. (b) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270.
29. (c) ibid., 1985, 82, 284.
30. (d) ibid., 1985, 82, 299.
31. Pople, J. A.; Head-Gordon, M.; Raghavachari, K. J. Chem. Phys. 1987, 87, 5968.
32. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, Jr., J. A.; 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.; Baboul, A. G.; Stefanov, B. B. ; Liu, Liashenko, G. ; Piskorz, A.; Komaromi, P.; 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. and Pople, J. A. Gaussian, Inc., Pittsburgh PA, 2003.
33. (a) Pyykkö, P.; Desclaux, J.-P. Acc. Chem. Res. 1979, 12, 276.
34. (b) Kutzelnigg, W. Angew. Chem., Int. Ed. Engl. 1984, 23, 272.
35. (c) Pyykkö, P. Chem. Rev. 1988, 88, 563.
36. (d) Pyykkö, P. Chem. Rev. 1997, 97, 597.
37. (a) Su, M.-D.; Chu, S.-Y. Inorg. Chem. 1999, 38, 4819.
38. (b) Su, M.-D. J. Phys. Chem. A. 2002, 106, 9563.
39. Hammond, G. S. J. Am. Chem. Soc. 1954, 77, 334.
40. For details, see: (a) Shaik, S.; Schlegel, H. B.; Wolfe, S. In Theoretical Aspects of Physical Organic Chemistry, John Wiley & Sons Inc., USA, 1992.
41. (b) Pross, A. In Theoretical and Physical principles of Organic Reactivity, John Wiley & Sons Inc., USA, 1995.
42. (c) Shaik, S. Prog. Phys. Org. Chem. 1985, 75, 197.
43. For the first paper that originated the CM model, see:
44. (a) Shaik, S. J. Am. Chem. Soc. 1981, 103, 3692. For information about the most updated review of the CM model, one can see:
45. (b) Shaik, S.; Shurki, A. Angew. Chem., Int. Ed. 1999, 38, 586.
46. Su, M.-D. Chem. Eur. J. 2004, 10, 5877.
47. (a) Hoffmann, R. J. Am. Chem. Soc. 1968, 90, 1475.
48. (b) Zurawski, B.; Kutzelnigg, W. J. Am. Chem. Soc. 1978, 100, 2654.
49. (c) Rondan, N. G.; Houk, K. N.; Moss, R. A. J. Am. Chem. Soc. 1980, 102, 1770.
50. Su, M.-D. J. Phys. Chem. 1996, 100, 4339 and related references therein.