Strong Conformational Consequences of Hyperconjugation

Journal of the American Chemical Society

Volumn 94, Issue 17, 1972, Pages 6221-6223

  Hoffmann, Roald ^a   Radom, Leo ^b   Pople, John A ^b   Von Schleyer, Paul R ^c   Hehre, Warren J ^d   Salem, Lionel ^e  

^a Department of Obstetrics Gynecology   (United States)

^b CARNEGIE MELLON UNIVERSITY   (United States)

^c PRINCETON UNIVERSITY   (United States)

^d UNIVERSITÉ PARIS SACLAY   (France)

^e ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33947088922     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00772a064     Document Type: Article

References (34)

1. The molecular orbital representation of hyperconjugation was introduced by R. S. Mulliken, J. Chem. Phys., 1, 492 (1933);
2. Proceedings of the Conference on Hyperconjugation, Tetrahedron, 5, 105 (1959).
3. M. J. S. Dewar and H. M. Schmeising, Tetrahedron, 6, 166 (1959);
4. M. J. S. Dewar, “Hyperconjugation,” Ronald Press, New York, N. Y., 1962.
5. For reviews of anionic fluorine hyperconjugation, see D. Holtz, Progr. Phys. Org. Chem., 8, 1 (1971),
6. and (b) W. A. Sheppard and C. M. Sharts, “Organic Fluorine Chemistry,” W. A. Benjamin, New York, N. Y., 1969, p 18 ff.
7. Recent discussions include B. M. Gimarc, J. Amer. Chem. Soc., 93, 593 (1971),
8. and P. H. Owens and A. Streitwieser, Jr., Tetrahedron, 27, 4471 (1971).
9. L. Salem, J. Amer. Chem. Soc., 90, 543 (1968);
10. K. Müller, Helv. Chim. Acta, 53, 1112 (1970), and references cited therein.
11. W. A. Lathan, W. J. Hehre, and J. A. Pople, J. Amer. Chem. Soc., 93, 808 (1971);
12. R. Sustmann, J. E. Williams, M. J. S. Dewar, L. C. Allen, and P. v. R. Schleyer, J. Amer. Chem. Soc., 91, 5350 (1969);
13. J. E. Williams, V. Buss, L. C. Allen, P. v. R. Schleyer, W. A. Lathan, W. J. Hehre, and J. A. Pople, J. Amer. Chem. Soc., 92, 2141 (1970);
14. J. E. Williams, V. Buss, and L. C. Allen, J. Amer. Chem. Soc., 93, 6867 (1971). (e) The CHLLLL3MMMMCHLLLL2MMMMNNNN–OOOO result is from unpublished work by W. J. Hehre.
15. G. V. Pfeiffer and J. G. Jewett, J. Amer. C em. Soc., 92, 2143 (1970);
16. L. J. Massa, S. Ehrenson, and M. Wolfsberg, Int. J. Quantum Chem., 4, 625 (1970);
17. L. J. Massa, S. Ehrenson, M. Wolfsberg, and C. A. Frishberg, Chem. Phys Lett., 11, 196 (1971).
18. The arguments may be found, among other sources, in E. Heilbronner and H. Bock, “Das HMO Modell und seine Anwendung,” Verlag Chemie, Weinheim Bergstr., Germany, 1968, p 168 ff.
19. L. Radom, J. A. Pople, and P. v. R. Schleyer, submitted for publication in J. Amer. Chem. Soc.
20. Similar conclusions on FCLLLL2MMMM-CHLLLL2MMMM+ are reported by D. T. Clark and D. M. J. Lilley, Chem. Commun., 603 (1970);
21. D. T. Clark, Proc. Int. Congr. Pure Appl. Chem., 1, 31 (1971).
22. Compare also extended Hückel calculations on BrCHLLLL2MMMM-CHLLLL2MMMMNNNN+OOOO by G. Heublein and P. Hallpap, J. Prakt. Chem., 312, 245 (1970), and
23. CNDO/2 calculations on pyramidal FCHLLLL2MMMM-CHLLLL2MMMMNNNN–OOOO by D. Holtz, A. Streitwieser, and R. G. Jesaitis, Tetrahedron Lett., 4529 (1969).
24. T. G. Traylor, W. Hanstein, H. J. Berwin, N. A. Clinton, and R. S. Brown, J. Amer. Chem. Soc., 93, 5715 (1971), and references cited therein.
25. P. J. Krusic and J. K. Kochi, J. Amer. Chem. Soc., 93, 846 (1971);
26. T. Kawamura and J. K. Kochi, J. Amer. Chem. Soc., 94, 648 (1972);
27. J. Organometal. Chem., 30, C8 (1971);
28. T. Kawamura, D. J. Edge, and J. K. Kochi, J. Amer. Chem. Soc., 94, 1752 (1972);
29. A. R. Lyons and M. C. R. Symons, Chem. Commun., 1068 (1971);
30. J. Amer. Chem. Soc., 93, 7330 (1971).
31. For a detailed analysis of torsional barriers, see L. Radom, W. J. Hehre, and J. A. Pople, J. Amer. Chem. Soc., 94, 2371 (1972).
32. See also S. Wolfe, A. Rauk, L. M. Tel, and I. G. Csizmadia, J. Chem. Soc B, 136 (1971).
33. See, inter alia, R. D. Bach and P. A. Scherr, J. Amer. Chem. Soc., 94, 220 (1972), and references cited therein;
34. J. M. J. Tronchet and Br. Baehler, Helv. Chim. Acta, 54, 546 (1971).