Role of conjugation in the stabilities and rotational barriers of formamide and thioformamide. An ab initio valence-bond study

Journal of the American Chemical Society

Volumn 119, Issue 40, 1997, Pages 9478-9482

  Lauvergnat, David ^a   Hiberty, Philippe C ^a  

^a UNIVERSITÉ PARIS SACLAY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

FORMAMIDE; FUNCTIONAL GROUP; THIOFORMAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CONFORMATION; CONJUGATION; MOLECULAR STABILITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ROTATION;

EID: 0030732055     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9639426     Document Type: Article

References (28)

1. Pauling, L. The Nature of the Chemical Bond; Cornell University Press: Cornell, 1960.
2. Wheland, G. W. Resonance in Organic Chemistry; Wiley: New York, 1955.
3. Streitwieser, A.; Heathcock, C. H.; Kosower, E. M. Introduction to Organic Chemistry, 4th ed.; Macmillan: New York, NY, 1992.
4. Flegg, R. H.; Harcourt, R. D. J. Mol Struct. (Theochem) 1988, 164, 67.
5. Wiberg, K. B.; Laidig, K. E. J. Am. Chem. Soc. 1987, 109, 5935.
6. Wiberg, K. B.; Breneman, C. L. J. Am. Chem. Soc. 1992, 114, 831.
7. (a) Bader, R. F. W. Acc. Chem. Res. 1985, 18, 9.
8. (b) Bader, R. F. W. Atoms in Molecules: A Quantum Theory, Oxford University Press: Oxford, 1990.
9. Wiberg, K. B.; Rablen, P. R. J. Am. Chem. Soc. 1995, 117, 2201.
10. Wiberg, K. B.; Rablen, P. R. J. Am. Chem. Soc. 1993, 115, 9234.
11. Laidig, K. E.; Cameron, L. M. J. Am. Chem. Soc. 1996, 118, 1737.
12. Perrin, C. L. J. Am. Chem. Soc. 1991, 113, 2865.
13. Gatti, C.; Fantucci, P. J. Phys. Chem. 1993, 97, 11677.
14. Laidig, K. E. J. Am. Chem. Soc. 1992, 114, 7912.
15. (a) Yamada, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1113.
16. (b) Yamada, S. J. Org. Chem. 1996, 61, 941.
17. Bennet, A. J.; Somayaji, V.; Brown, R. S.; Santarsiero, B. D. J. Am. Chem. Soc. 1991, 113, 7563.
18. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650.
19. van Lenthe, J. H.; Balint-Kurti, G. G. J. Chem. Phys. 1983, 78, 5699.
20. (a) Verbeek, J. Ph.D. Thesis, University of Utrecht, 1990.
21. (b) Verbeek, J.; van Lenthe, J. H. J. Mol. Struct. (Theochem) 1991, 229, 115.
22. (c) Verbeek, J.; van Lenthe, J. H. Int. J. Quantum. Chem. 1991, 40, 201.
23. (d) Verbeek, J.; van Lenthe, J. H.; Pulay, P. Mol. Phys. 1991, 73, 1159.
24. Verbeek, J.; Langenberg, J. H.; Byrman, C. P.; van Lenthe, J. H., TURTLE - An ab initio VB/VBSCF/VBCI program, Utrecht, 1993.
25. Frisch, M. J.; Trucks, G. W.; Head-Gordon, M.; Gill, P. M. W.; Wong, M. W.; Foresman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M. A.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. Gaussian 92, Revision C3; Gaussian, Inc.: Pittsburgh, PA, 1992.
26. Hiberty, P. C.; Byrman, C. P. J. Am. Chem. Soc. 1995, 117, 9875.
27. Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
28. Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.