The physical origin of saytzeff's rule

Angewandte Chemie - International Edition

Volumn 48, Issue 31, 2009, Pages 5724-5728

  Braida, Benoit ^a   Prana, Vinca ^a   Hiberty, Philippe C ^b  

^a SORBONNE UNIVERSITÉ   (France)

^b UNIVERSITÉ PARIS SACLAY   (France)

Author keywords

Ab initio calculations; Hyperconjugation; Saytzeff s rule; Valence bond theory

Indexed keywords

AB INITIO; AB INITIO CALCULATIONS; HYPERCONJUGATION; SAYTZEFF S RULE; SUBSTITUTED ALKENE; VALENCE BOND THEORY; VALENCE-BOND METHOD;

CHEMICAL BONDS;

OLEFINS;

EID: 70349784871     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200901923     Document Type: Article

References (32)

1. A. M. Saytzeff, Justus Liebigs Ann. Chem. 1875, 179, 296.
2. D. R. Palleros, Organic Chemistry, Wiley, New York, 2000, p. 260.
3. R. J. Ouellette, Organic Chemistry, Prentice-Hall, Upper Saddle River, NJ, 1996, p. 326.
4. th ed., W. H. Freeman, New York, 2002.
5. th ed., MacMillan, New York, 1992.
6. S. Shaik, P. C. Hiberty, A Chemist's Guide to Valence Bond Theory, Wiley, Hoboken, NJ, 2008.
7. P. C. Hiberty, S. Shaik, J. Comput. Chem. 2007, 28, 137.
8. -1 between the eclipsed and the staggered (gauche)-conf ormation, and is larger in the latter. See: a) Y Mo, W. Wu, L. Song, M. Lin, Q. Zhang, J. Gao, Angew. Chem. 2004, 116, 2020;
9. Angew. Chem. Int. Ed. 2004, 43, 1986;
10. b) Y. Mo, I. Gao, Acc. Chem. Res. 2007, 40, 113.
11. A. E. Reed, L. A. Curtiss, F. Weinhold, Chem. Rev. 1988, 88, 899.
12. a) D. Cappel, S. Tullmann, A. Krapp, G. Frenking, Angew. Chem. 2005, 117, 3683;
13. Angew. Chem. Int. Ed. 2005, 44, 3617;
14. b) I. Fernandez, G. Frenking, Faraday Discuss. 2007, 135, 403;
15. c) I. Fernandez, G. Frenking, Chem. Eur. J. 2006, 12, 3617.
16. F. M. Bickelhaupt, E. J. Baerends, Angew. Chem. 2003, 115, 4315;
17. Angew. Chem. Int. Ed. 2003, 42, 4183.
18. a) Y. Mo, Y. Zhang, J. Gao, J. Am. Chem. Soc. 1999, 121, 5737;
19. b) Y Mo, J. Org. Chem. 2004, 69, 5563;
20. For an extension of the BLW method to the density functional level, see: c) Y Mo, L. Song, Y. Lin, J. Phys. Chem. A 2007, 111, 8291.
21. D. Lauvergnat, P. C. Hiberty, J. Am. Chem. Soc. 1997, 119, 9478.
22. P. C. Hiberty, C. P. Byrman, J. Am. Chem. Soc. 1995, 117, 9875.
23. a) Y Mo, P. v. R. Schleyer, W. Wu, M. Lin, Q. Zhang, J. Gao, J. Phys. Chem. A 2003, 107, 10011;
24. b) M. Linares, S. Humbel, B. Braida, Faraday Discuss. 2007, 135, 273.
25. Y. Mo, P. v. R. Schleyer, Chem. Eur. J. 2006, 12, 2009.
26. Y. Mo, J. Phys. Chem. A 2009, 113, 5163.
27. a) W. A. Goddard III, Phys. Rev. 1967, 157, 81;
28. b) W. A. Goddard III, T. H. Dunning, Jr., W. J. Hunt, P. J. Hay, Acc. Chem. Res. 1973, 6, 368.
29. a) L. Song, Y. Mo, Q. Zhang, W. Wu, XMVB: An Ab Initio Nonorthogonal Valence Bond Program, Xiamen University, Xiamen, 1999;
30. b) L. Song, Y. Mo, Q. Zhang, W. Wu, J. Comput. Chem. 2005, 26, 514;
31. c) L. Song, J. Song, Y. Mo, W. Wu, J. Comput. Chem. 2009, 30, 399.
32. Gaussian03, Revision D.01, M. J. Frisch et al., Gaussian, Inc., Wallingford CT, 2004.