Stabilization in Neutral Bicyclic Sulfoxide Compounds

Journal of Computational Chemistry

Volumn 21, Issue 4, 2000, Pages 322-327

  El Bergmi, Redouan ^a   Dobado, J A ^a   Portal, Dolores ^a   Molina, José Molina ^a  

^a UNIVERSITY OF GRANADA   (Spain)

Author keywords

ab initio calculations; DFT calculations; Electronic structure; Hypervalent compounds; Magnetic properties

Indexed keywords

EID: 0001342634     PISSN: 01928651     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1096-987X(200003)21:4<322::AID-JCC7>3.0.CO;2-F     Document Type: Article

References (35)

1. Prakash, G. K. S.; Schleyer, P. v. R., Eds. Stable Carbocation Chemistry; Wiley: New York, 1997.
2. Brown, H. C. In The Nonclassical Ion Problem; Plenum Press: New York, 1977.
3. Olah, G. A.; Schleyer, P. v. R., Eds. Carbonium Ions; Wiley: New York, 1968.
4. Olah, G. A.; Prakash, G. K. S.; Williams, R. E.; Field, L. D.; Wade, K. Hypercarbon Chemistry; Wiley: New York, 1987.
5. Laube, T. Acc Chem Res 1995, 28, 399.
6. (a) Saunders, M.; Kates, M. H. J Am Chem Soc 1980, 102, 6867;
7. (b) Myhre, P. C.; Webb, G. G.; Yannoni, C. S. J Am Chem Soc 1990, 112, 8991;
8. (c) Koch, C. W.; Liu, B.; De Frees, D. J.; Sunko, D. E.; Vancik, H. Angew Chem Int Ed Engl 1990, 19, 183.
9. Schleyer, P. v. R.; Maerker, C. Pure Appl Chem 1995, 67, 755.
10. Schleyer, P. v. R.; Sieber, S. Angew Chem Int Ed Engl 1993, 32, 1606.
11. Jarret, R. M.; Saunders, M. J Am Chem Soc 1987, 109, 3366.
12. Winstein, S.; Ordronneau, C. J Am Chem Soc 1960, 82, 2084.
13. Olah, G. A.; Schleyer, P. v. R., Eds. Carbonium Ions; Wiley: New York, Vol. III, 1972, p. 968.
14. Bremer, M.; Schötz, K.; Schleyer, P. v. R.; Fleischer, U.; Schindler, M.; Kutzelnigg, W.; Koch, W.; Pulay, P. Angew Chem Int Ed Engl 1989, 28, 1042.
15. Schulman, J. M.; Disch, R. L.; Schleyer, P. v. R.; Buhl, M.; Bremer, M.; Koch, W. J Am Chem Soc 1992, 114, 7897.
16. Prakash, G. K. S.; Schleyer, P. v. R., Eds. Stable Carbocation Chemistry; Wiley: New York, 1968, p. 67.
17. Laube, T.; Lohse, C. J Am Chem Soc 1994, 116, 9001.
18. Goldstein, M. J.; Hoffmann, R. J Am Chem Soc 1971, 93, 6193.
19. Allen, F. H.; Kennard, O. Chemical Design Automation News 1993, 8, 31.
20. Li, Y. Q.; Thiemann, T.; Sawada, T.; Tashiro, M. J Chem Soc Perking Trans I 1994, 2323.
21. Li, Y. Q.; Thiemann, T.; Sawada, T.; Mataka, S.; Tashiro, M. Eur J Org Chem 1998, 1841.
22. Treiber, A.; Dansette, P. M.; El-Amri, H.; Girault, J. P.; Ginderow, D.; Mornon, J. P.; Mansuy, D. J Am Chem Soc 1997, 119, 1565.
23. Dobado, J. A.; Martínez-García, H.; Molina, J.; Sundberg, M. R. J Am Chem Soc 1998, 120, 8461.
24. Dobado, J. A.; Martínez-García, H.; Molina, J.; Sundberg, M. R. J Am Chem Soc 1999, 121, 3156.
25. Curtiss, L. A.; Raghavachari, K.; Trucks, G. W.; Pople, J. A. J Chem Phys 1991, 94, 7221.
26. 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.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.4.; Gaussian, Inc.: Pittsburgh, PA, 1998.
27. Biegler-König, F. W.; Bader, R. F. W.; Tang, T.-H. J Comput Chem 1982, 3, 317.
28. Bader, R. F. W. Atoms in Molecules: A Quantum Theory; Clarendon Press: Oxford, 1990.
29. Bader, R. F. W. Chem Rev 1991, 91, 893.
30. Wolinski, K.; Hilton, J. F.; Pulay, P. J Am Chem Soc 1990, 112, 8251.
31. Olah, G. A.; Liang, G.; Mateescu, G. D.; Riemenschneider, J. L. J Am Chem Soc 1973, 95, 8698.
32. Olah, G. A.; Liang, C. J Am Chem Soc 1975, 97, 6803.
33. This σ* participation has been proposed in the X - O bond for the phosphine oxides and sulfoxides, see Reed, A. E.; Schleyer, P. v. R. J Am Chem Soc 1990, 112, 1434; and Gilheany, D. G. Chem Rev 1994, 94, 1339.
34. This σ* participation has been proposed in the X - O bond for the phosphine oxides and sulfoxides, see Reed, A. E.; Schleyer, P. v. R. J Am Chem Soc 1990, 112, 1434; and Gilheany, D. G. Chem Rev 1994, 94, 1339.
35. Fradera, X.; Austen, M. A.; Bader, R. F. W. J Phys Chem A 1999, 103, 304.