Nitrogen inversion barrier of 2-methyl-2-azabicyclo[2.2.1]heptane. The role of torsional strain in pyramidal inversion

Journal of Organic Chemistry

Volumn 61, Issue 4, 1996, Pages 1284-1289

  Forsyth, David A ^a   Zhang, Weiyi ^a   Hanley, John A ^a  

^a NORTHEASTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000714307     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951940i     Document Type: Article

References (45)

1. Lehn, J. M. Fortschr. Chem. Forsch. 1970, 15, 311.
2. Lambert J. R. Top. Stereochem. 1971, 6, 19.
3. Rauk, A.; Allen, L. C.; Mislow, K. Angew. Chem., Int. Ed. Engl, 1970, 9, 400.
4. Acyclic Organonitrugen Stereodynamics; Lambert, J B., Takeuchi, Y., Eds.; VCH: New York, 1992.
5. Cyclic Organanitrogen Stereodynamics; Lambert, J. B., Takeuchi, Y. ,Eds.; VCH: New York, 1992.
6. Bushweller, C. H., ref 4, Chapter 1.
7. Delpuech, J.-J., ref 5, Chapter 7.
8. Jackson, W. R.; Jennings, W. B. Tetrahedron Lett. 1974, 1837.
9. Lunazzi, L.; Macciantelli, D.; Grossi, L. Tetrahedron 1983, 39, 305.
10. Anderson, J. E.; Casarini, D.; Lunazzi, L. J. Chem. Soc., Perkin Trans. 2 1990, 1791.
11. For theoretical discussions of the inversion-rotation process in methylamines, see: (a) Eades, R. A.; Weil, D. A.; Dixon, D. A.; Douglass, C. H., Jr., J. Phys. Chem. 1981, 85, 976. (b) Kölmel, C.; Ochsenfeld, C.; Ahlrichs, R. Theor. Chim, Acta 1991, 82, 271. (c) Halpern, A. M., Ramachandran, B. R. J. Phys. Chem. 1992, 96, 9832.
12. For theoretical discussions of the inversion-rotation process in methylamines, see: (a) Eades, R. A.; Weil, D. A.; Dixon, D. A.; Douglass, C. H., Jr., J. Phys. Chem. 1981, 85, 976. (b) Kölmel, C.; Ochsenfeld, C.; Ahlrichs, R. Theor. Chim, Acta 1991, 82, 271. (c) Halpern, A. M., Ramachandran, B. R. J. Phys. Chem. 1992, 96, 9832.
13. For theoretical discussions of the inversion-rotation process in methylamines, see: (a) Eades, R. A.; Weil, D. A.; Dixon, D. A.; Douglass, C. H., Jr., J. Phys. Chem. 1981, 85, 976. (b) Kölmel, C.; Ochsenfeld, C.; Ahlrichs, R. Theor. Chim, Acta 1991, 82, 271. (c) Halpern, A. M., Ramachandran, B. R. J. Phys. Chem. 1992, 96, 9832.
14. Nelsen, S, F.; Ippoliti, J. T.; Frigo, T. B.; Petillo, P. A. J. Am. Chem. Soc. 1989, 111, 1776.
15. Davies, J. W.; Durant, M. L.; Walker, M. P.; Belkacemi, D.; Malpass, J R. Tetrahedron 1992, 48, 861 and references therein.
16. Bushweller, C H.; Brown, J. H.; Dimeglio, C. M.; Gribble, G. W.; Eaton, J. T.; LeHoullioer, C. S.; Olson, E. R. J. Org. Chem. 1995, 60, 268 and references therein.
17. Lehn, J. M.; Wagner, J. Chem. Commun. 1970, 414.
18. Nelsen, S. F.; Weisman, G. R. J. Am. Chem. Soc. 1976, 98, 1842.
19. Brown, H. C. The Nonclassical Ion Problem; Plenum: New York, 1977.
20. Menger, F. M.; Permis, M; Jerkunica, J. M.; Glass, L. E. J. Am. Chem. Soc. 1978, 100, 1503.
21. (a) Grutzner, J. B.; Jautelat, M.; Dence, J. B.; Smith, R. A.; Roberts, J. D. J. Am. Chem. Soc. 1970, 92, 7107.
22. (b) Stothers, J. B. Carbon-13 NMR Spectroscopy; Academic Press: New York 1972; p 68.
23. 13C NMR Spectroscopy, 2nd ed.; Verlag Chemie: New York, 1978; pp 74, 210.
24. (b) Kalinowski, H.-O.; Berger, S.; Braun, S. Carbon-13 NMR Spectroscopy; Wiley: Chichester, 1988, p 109ff.
25. A locally modified version of the DNMR5 (Stephenson, D. S.; Binsch, G.) program further adapted by C. B. LeMaster, C. L. LeMaster, and N. S. True. Program No. QCMP059, Quantum Chemistry Program Exchange, Indiana University, Bloomington, IN 47405.
26. (a) Drakenberg, T.; Lehn, J. M. J. Chem. Soc., Perkin Trans. 2 1972, 532.
27. (b) Schneider, H.-J.; Sturm, L. Angew. Chem. Int. Ed. Engl. 1976, 15, 545.
28. (c) Casarini, D.; Davalli, S.; Lunazzi, L.; Maceiantelli, D. J. Org. Chem. 1989, 54, 4616.
29. 3OH: (a) Larson, J. W.; McMahon, T B. J. Am. Chem. Soc. 1984, 106, 517. (b) Larson, J. W.; McMahon, T. B. J. Am. Chem. Soc. 1987, 109, 6230.
30. 3OH: (a) Larson, J. W.; McMahon, T B. J. Am. Chem. Soc. 1984, 106, 517. (b) Larson, J. W.; McMahon, T. B. J. Am. Chem. Soc. 1987, 109, 6230.
31. Forsyth, D. A.; Johnson, S. M. J. Am. Chem. Soc. 1994, 116, 11481.
32. Halpern, A. M.; Ondrechen, M. H.; Ziegler, L. D. J. Am. Chem. Soc. 1986, 108, 3907.
33. Gajewski, J. J.; Gilbert, K. E.; McKelvie, H. In Advances in Molecular Modelling; Liotta, D., Ed.; JAI Press: Greenwich, CT, 1990; Vol. 2. PCMODEL, V. 4.0, Serena Software: Box 3076, Bloomington, IN.
34. Profeta, S , Jr.; Allinger, N. C. J. Am. Chem. Soc. 1985, 107, 1907.
35. Nelsen, S. F.; Weisman, G. R.; Clennan, E. L.; Peacock, V. E. J. Am. Chem. Soc. 1976, 98, 6893.
36. Barrier for equatorial to axial inversion in N-methylpiperidine derived as described in ref 7 from ultrasonic relaxation data: Gittins, V. M.; Heywood, P. J.; Wyn-Jones, E. J. Chem. Soc., Perkin Trans 2 1975, 1642.
37. Brown, J. H.; Bushweller, C. H. J. Am. Chem. Soc. 1992, 114, 8153.
38. Anet, F, A. L.; Anet, R. in Dynamic Nuclear Magnetic Resonance Spectroscopy; Jackman, L. M., Cotton, F. A., Eds.; Academic Press: New York, 1975; Chapter 14.
39. Binsch, G., ref 31, Chapter 3.
40. Sandstrom, J. Dynamic NMR Spectroscopy; Academic Press: London, 1982; Chapter 7.
41. Lambert, J. B.; Vagenas, A. R.; Somani, S. J. Am. Chem. Soc. 1981, 103, 6398.
42. The 3-membered ring case, 1-methylaziridine, was not included because MM2 parameters for the special case of the aziridine ring were not derived: see ref 27.
43. Larsen, S. D.; Grieco, P. A. J. Am. Chem. Soc. 1985, 107, 1768.
44. Schneider, W.; Dillman, R. Ber. 1963, 96, 2377.
45. Siegel, J. S.; Anet, F. A. L. J. Org. Chem. 1988, 53, 2629.