Axial and equatorial 1-methyl-1-cyclohexyl cation isomers both have chair conformations but differ in C-C and C-H hyperconjugation modes

Journal of the American Chemical Society

Volumn 118, Issue 15, 1996, Pages 3761-3762

  Rauk, A ^a   Sorensen, T S ^a   Maerker, C ^a   Carneiro, J W De M ^a   Sieber, S ^a   Schleyer, P V R ^a  

^a UNIVERSITY OF CALGARY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANE DERIVATIVE;

ARTICLE; DRUG STRUCTURE; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE; THEORY;

EID: 0029891974     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9531900     Document Type: Article

References (17)

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3. Kirchen, R. P.; Ranganayakulu, K.; Sorensen, T. S. J. Am Chem Soc. 1987, 109, 7811.
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5. Gauss, J. Chem Phys. Lett. 1992, 191, 614; J. Chem. Phys. 1993, 99, 3629. For a description of the GIAO approach, see: Ditchfield, R. Mol. Phys. 1974, 27, 789. Wolinski, K.; Hinton, J. F, Pulay, P. J. Am Chem Soc. 1990, 112, 851. For a recent application of GIAO-MP2 to carbocations, see: Sieber, S, Schleyer, P. von R., Gauss, J. J. Am Chem. Soc. 1993, 115, 6987.
6. Gauss, J. Chem Phys. Lett. 1992, 191, 614; J. Chem. Phys. 1993, 99, 3629. For a description of the GIAO approach, see: Ditchfield, R. Mol. Phys. 1974, 27, 789. Wolinski, K.; Hinton, J. F, Pulay, P. J. Am Chem Soc. 1990, 112, 851. For a recent application of GIAO-MP2 to carbocations, see: Sieber, S, Schleyer, P. von R., Gauss, J. J. Am Chem. Soc. 1993, 115, 6987.
7. Gauss, J. Chem Phys. Lett. 1992, 191, 614; J. Chem. Phys. 1993, 99, 3629. For a description of the GIAO approach, see: Ditchfield, R. Mol. Phys. 1974, 27, 789. Wolinski, K.; Hinton, J. F, Pulay, P. J. Am Chem Soc. 1990, 112, 851. For a recent application of GIAO-MP2 to carbocations, see: Sieber, S, Schleyer, P. von R., Gauss, J. J. Am Chem. Soc. 1993, 115, 6987.
8. Gauss, J. Chem Phys. Lett. 1992, 191, 614; J. Chem. Phys. 1993, 99, 3629. For a description of the GIAO approach, see: Ditchfield, R. Mol. Phys. 1974, 27, 789. Wolinski, K.; Hinton, J. F, Pulay, P. J. Am Chem Soc. 1990, 112, 851. For a recent application of GIAO-MP2 to carbocations, see: Sieber, S, Schleyer, P. von R., Gauss, J. J. Am Chem. Soc. 1993, 115, 6987.
9. Gauss, J. Chem Phys. Lett. 1992, 191, 614; J. Chem. Phys. 1993, 99, 3629. For a description of the GIAO approach, see: Ditchfield, R. Mol. Phys. 1974, 27, 789. Wolinski, K.; Hinton, J. F, Pulay, P. J. Am Chem Soc. 1990, 112, 851. For a recent application of GIAO-MP2 to carbocations, see: Sieber, S, Schleyer, P. von R., Gauss, J. J. Am Chem. Soc. 1993, 115, 6987.
10. 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: Gaussian, Inc.: Pittsburgh, PA, 1992.
11. Becke, A. D J. Chem. Phys. 1993, 98, 5648.
12. Several higher level single-point computations, e g., MP4/6-31G*// MP2/6-31G*, were also carried out (see Table 2 of the supporting information for a listing of the energies obtained)
13. See the supporting information for the geometry data for the two isomers of 1 at both levels of optimization
14. 11 cations.
15. Schleyer, P. von R.; Carneiro, J. W. de M.; Koch, W.; Forsythe, D. A. J. Am. Chem. Soc. 1991, 113, 3990.
16. Nevertheless, both minima do support at least one vibrational level; for the frequency data for both the Becke 3LYP and MP2 calculations, see the supporting information.
17. To be published later, together with data for other deuterated isotopomers of 1.