Density Functional Calculation of 1JC-H Coupling Constants in Cyclohexane and Diheterocyclohexanes. Repercussion of Stereoelectronic Effects on Coupling Constants

Journal of Physical Chemistry A

Volumn 103, Issue 7, 1999, Pages 932-937

  Cuevas, Gabriel ^a   Juaristi, Eusebio ^b   Vela, Alberto ^c  

^a UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

^b INSTITUTO POLITÉCNICO NACIONAL   (Mexico)

^c UNIVERSIDAD AUTÓNOMA METROPOLITANA   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000613891     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp983664s     Document Type: Article

References (56)

1. Bohlmann, F. Angew. Chem. 1957, 69, 641. Bohlmann, F. Chem. Ber. 1958, 91, 2157.
2. Bohlmann, F. Angew. Chem. 1957, 69, 641. Bohlmann, F. Chem. Ber. 1958, 91, 2157.
3. (a) Krueger, P. J.; Jan, J.; Wieser, H. J. Mol Struct. 1970, 5, 375.
4. (b) Berrnardi, F.; Schlegel, H.B.; Wolfe, S. J. Mol. Struct. 1976, 35, 149.
5. (c) McKean, D. C. Chem. Soc. Rev. 1978, 7, 399.
6. Hehre, W. J.; Radom, L.; Schleyer, P.v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
7. Perlin, A. S.; Casu, B. Tetrahedron Lett 1969, 2921.
8. (a) Bock, K.; Wiebe, L. Acta Chem. Scand. 1973, 27, 2676.
9. See also: (b) Rao, V. S.; Can. J. Chem. 1982, 60, 1067.
10. (c) Hansen, P. E. Prog. Nucl. Magn. Reson. Spectrosc. 1981, 14, 175.
11. Bailey, W. F.; Rivera, A. D.; Rossi, K. Tetrahedron Lett. 1988, 29, 5621.
12. (a) Wolfe, S.; Pinto, B. M.; Varma, V.; Leung, R. Y. N. Can. J. Chem. 1990, 69, 1051.
13. (b) Wolfe, S.; Kim, C.-K. Can. J. Chem. 1991, 69, 1408.
14. (a) Juaristi, E.; Cuevas, G. Tetrahedron Lett. 1992, 33, 1847.
15. (b) Juaristi, E.; Cuevas, G.; Fiores-Vela, A. Tetrahedron Lett. 1992, 33, 6927.
16. Juaristi, E.; Cuevas, G.; Vela, A. J. Am. Chem. Soc. 1994, 116, 5796.
17. Eliel, E. L.; Rao, V. S.; Vierhapper, F. W.; Juaristi, G. Z. Tetrahedron Lett. 1975, 4339.
18. Cuevas, G.; Juaristi, E.; Vela, A. J. Mol. Struct. (THEOCHEM) 1997, 418, 231.
19. (a) Malkin, V. G.; Malkina, O. L.; Casida, M. E.; Salahub, D. R. J. Am. Chem. Soc. 1994, 116, 5898.
20. (b) Malkin, V. G.; Malkina, O. L.; Eriksson, L. A.; Salahub, D. R. In Modern Density Functional Theory. A Tool for Chemistry; Seminario, J. M., Politzer, P., Eds.; Elsevier: Amsterdam, 1995.
21. Kowalewski, J. Prog. NMR Spectrosc. 1977, 11, 1. Kowalewski, J. Ann. Rep. NMR Spectrosc. 1982, 12, 81. Fukui, H. Nucl. Magn. Reson. 1991, 20, 107. Fukui, H. Nucl. Magn. Reson., 1993, 22, 138. Oddershede, J. Nucl. Magn. Reson. 1992, 21, 113. Peruchena, N. M.; Contreras, R. H. J. Mol. Struct. (THEOCHEM) 1995, 338, 25.
22. Kowalewski, J. Prog. NMR Spectrosc. 1977, 11, 1. Kowalewski, J. Ann. Rep. NMR Spectrosc. 1982, 12, 81. Fukui, H. Nucl. Magn. Reson. 1991, 20, 107. Fukui, H. Nucl. Magn. Reson., 1993, 22, 138. Oddershede, J. Nucl. Magn. Reson. 1992, 21, 113. Peruchena, N. M.; Contreras, R. H. J. Mol. Struct. (THEOCHEM) 1995, 338, 25.
23. Kowalewski, J. Prog. NMR Spectrosc. 1977, 11, 1. Kowalewski, J. Ann. Rep. NMR Spectrosc. 1982, 12, 81. Fukui, H. Nucl. Magn. Reson. 1991, 20, 107. Fukui, H. Nucl. Magn. Reson., 1993, 22, 138. Oddershede, J. Nucl. Magn. Reson. 1992, 21, 113. Peruchena, N. M.; Contreras, R. H. J. Mol. Struct. (THEOCHEM) 1995, 338, 25.
24. Kowalewski, J. Prog. NMR Spectrosc. 1977, 11, 1. Kowalewski, J. Ann. Rep. NMR Spectrosc. 1982, 12, 81. Fukui, H. Nucl. Magn. Reson. 1991, 20, 107. Fukui, H. Nucl. Magn. Reson., 1993, 22, 138. Oddershede, J. Nucl. Magn. Reson. 1992, 21, 113. Peruchena, N. M.; Contreras, R. H. J. Mol. Struct. (THEOCHEM) 1995, 338, 25.
25. Kowalewski, J. Prog. NMR Spectrosc. 1977, 11, 1. Kowalewski, J. Ann. Rep. NMR Spectrosc. 1982, 12, 81. Fukui, H. Nucl. Magn. Reson. 1991, 20, 107. Fukui, H. Nucl. Magn. Reson., 1993, 22, 138. Oddershede, J. Nucl. Magn. Reson. 1992, 21, 113. Peruchena, N. M.; Contreras, R. H. J. Mol. Struct. (THEOCHEM) 1995, 338, 25.
26. Kowalewski, J. Prog. NMR Spectrosc. 1977, 11, 1. Kowalewski, J. Ann. Rep. NMR Spectrosc. 1982, 12, 81. Fukui, H. Nucl. Magn. Reson. 1991, 20, 107. Fukui, H. Nucl. Magn. Reson., 1993, 22, 138. Oddershede, J. Nucl. Magn. Reson. 1992, 21, 113. Peruchena, N. M.; Contreras, R. H. J. Mol. Struct. (THEOCHEM) 1995, 338, 25.
27. Becke, A. D. Can. J. Chem. 1988, 88, 1052. Becke, A. D. Phys. Rev. A 1988, 38, 3098.
28. Becke, A. D. Can. J. Chem. 1988, 88, 1052. Becke, A. D. Phys. Rev. A 1988, 38, 3098.
29. Perdew, J. P. Phys. Rev. Lett. 1985, 55, 1665.
30. Cf.: Andzelm, J.; Wimmer, E. J. Chem. Phys. 1992, 96, 1280.
31. Andzel, J. In Density Functional Methods in Chemistry; Labanowski, J., Ed.; Springer: New York, 1991; p 155.
32. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Wong, M. W.; Foresman, J. B.; Robb, M. A.; Head-Gordon, M.; 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/DFT, Revision G; Gaussian, Inc.: Pittsburgh, PA, 1993.
33. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623. Becke, A. D. J. Chem. Phys. 1993, 98, 1372, 5648.
34. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623. Becke, A. D. J. Chem. Phys. 1993, 98, 1372, 5648.
35. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. 1988, B37, 785-789. Miehlich, B.; Savin, A. Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200.
36. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. 1988, B37, 785-789. Miehlich, B.; Savin, A. Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200.
37. Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200.
38. Malkin, V. G.; Malkina, O. L.; Salahub, D. R. Chem. Phys. Lett. 1994, 221, 91.
39. Malkina, O. L.; Salahub, D. R.; Malkin, V. G. J. Chem. Phys. 1996, 105, 8793.
40. Salahub, D. R.; Fournier, R.; Mlynarski, P.; Papal, I.; St-Amant, A.; Uskio, J. In Density Functional Methods in Chemistry, Labanowski, J. K., Anzelm, J. W., Eds.; Springer: New York, 1991; p 77.
41. St-Amant, A.; Salahub, D. R. Chem. Phys. Lett. 1990, 169, 387.
42. Perdew, J. P.; Wang, Y. Phys. Rev. B 1986, 33, 8800.
43. Perdew, J. P. Phys. Rev. B 1986, 33, 8822; 1986, 34, 7406.
44. Perdew, J. P. Phys. Rev. B 1986, 33, 8822; 1986, 34, 7406.
45. Kutzelnigg, W.; Fleischer, U.; Schindler, M. In NMR - Basic Principles and Progress; Springer-Verlag: Heidelberg, 1990; Vol. 33, p 165.
46. Glendening, E. D.; Reed, A. E. Carpenter, J. E.; Weinhold, F.; NBO 3.1; Theoretical Chemistry Institute, University of Wisconsin: Madison, WI, 1994. Reed, E. A.; Weinstock, R. B.; Weinhold, F. J. J. Chem. Phys. 1985, 83, 735. Reed, E. A.; Weinhold, F. J. J. Chem. Phys. 1985, 83, 1736. Reed, E. A.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 83, 735.
47. Glendening, E. D.; Reed, A. E. Carpenter, J. E.; Weinhold, F.; NBO 3.1; Theoretical Chemistry Institute, University of Wisconsin: Madison, WI, 1994. Reed, E. A.; Weinstock, R. B.; Weinhold, F. J. J. Chem. Phys. 1985, 83, 735. Reed, E. A.; Weinhold, F. J. J. Chem. Phys. 1985, 83, 1736. Reed, E. A.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 83, 735.
48. Glendening, E. D.; Reed, A. E. Carpenter, J. E.; Weinhold, F.; NBO 3.1; Theoretical Chemistry Institute, University of Wisconsin: Madison, WI, 1994. Reed, E. A.; Weinstock, R. B.; Weinhold, F. J. J. Chem. Phys. 1985, 83, 735. Reed, E. A.; Weinhold, F. J. J. Chem. Phys. 1985, 83, 1736. Reed, E. A.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 83, 735.
49. Glendening, E. D.; Reed, A. E. Carpenter, J. E.; Weinhold, F.; NBO 3.1; Theoretical Chemistry Institute, University of Wisconsin: Madison, WI, 1994. Reed, E. A.; Weinstock, R. B.; Weinhold, F. J. J. Chem. Phys. 1985, 83, 735. Reed, E. A.; Weinhold, F. J. J. Chem. Phys. 1985, 83, 1736. Reed, E. A.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 83, 735.
50. Chertkov, V. A.; Sergeyev, N. M. J. Am. Chem. Soc. 1977, 99, 6750.
51. (a) Anderson, J. E.; Bloodworth, A. J.; Cai, J.; Davies, A. G.; Tallant, N. A. J. Chem. Soc., Chem. Commun. 1992, 1689.
52. (b) Anderson, J. E.; Bloodworth, A. J.; Cai, J.; Davies, A. G.; Schiesser, C. H. J. Chem. Soc., Perkin Trans. 2 1993, 601.
53. (a) Anet, F. A. L.; Kopelevich, M. J. Am. Chem. Soc. 1986, 108, 2109.
54. (b) Anet, F. A. L.; Kopelevich, M. J. Chem. Soc., Chem. Commun. 1987, 595.
55. (c) Forsyth, D. A.; Hanley, J. A. J. Am. Chem. Soc. 1987, 109, 7930.
56. Anderson, J. E.; Cai, J.; Davies, A. G. J. Chem. Soc., Perkin Trans. 2 1997, 2633. We are grateful to Professor Davies for providing us with a copy of this manuscript prior to publication.