A theoretical analysis of the conformational behaviour of substituted methylenecyclohexanes

Canadian Journal of Chemistry

Volumn 81, Issue 10, 2003, Pages 1101-1107

  Mawhinney, Robert C ^a   Muchall, Heidi M ^a   Lessard, Jean ^b  

^a Gina Cody School of Engineering and Computer Science   (Canada)

^b UNIVERSITÉ DE SHERBROOKE   (Canada)

Author keywords

Anomeric effect; Conformational analysis; Methylenecyclohexanes; Unsaturation effect

Indexed keywords

COMPOSITION; COMPUTATIONAL METHODS; CONFORMATIONS; UNSATURATED COMPOUNDS;

ANOMERIC EFFECTS; DENSITY FUNCTIONAL THEORY;

HYDROCARBONS;

CARBENOID; CYCLOHEXANE DERIVATIVE;

ARTICLE; EQUILIBRIUM CONSTANT; HYBRIDIZATION; QUALITATIVE ANALYSIS; QUANTITATIVE ANALYSIS; SOLVATION; THEORETICAL STUDY;

EID: 0344873617     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v03-137     Document Type: Article

References (40)

1. A.J. Kirby. Stereoelectronic effects. Oxford University Press, New York. 1996.
2. A.J. Kirby and N.H. Williams. In Anomeric effect and associated stereoelectronic effects. Edited by G.R.J. Thatcher. ACS Symposium Series 539. American Chemical Society, Washington, D.C. 1993. pp. 55-69.
3. J. Lessard, M.T.P. Viet, R. Martino, and J.K. Saunders. Can. J. Chem. 55, 1015 (1977).
4. M.T.P. Viet, J. Lessard, and J.K. Saunders. Tetrahedron Lett. 4, 317 (1979).
5. J. Lessard, J.K. Saunders, and M.T.P. Viet. Tetrahedron Lett. 23, 2059 (1982).
6. A. Ouedraogo, T.P.V. Minh, J.K. Saunders, and J. Lessard. Can. J. Chem. 65, 1761 (1987).
7. H.M. Muchall, P.R.N. Kamya, and J. Lessard. Can. J. Chem. 81, 689 (2003).
8. V. Barone, M. Cossi, and J. Tomasi. J. Comput. Chem. 19, 404 (1998).
9. V. Barone, M. Cossi, and J. Tomasi. J. Chem. Phys. 107, 3210 (1997).
10. M. Cossi, V. Barone, R. Cammi, and J. Tomasi. Chem. Phys. Lett. 255, 327 (1996).
11. J.P. Perdew, M. Ernzerhof, and K. Burke. J. Chem. Phys. 105, 9982 (1996).
12. C. Adamo and V. Barone. J. Chem. Phys. 110, 6158 (1999).
13. R. Improta, C. Benzi, and V. Barone. J. Am. Chem. Soc. 123, 12 568 (2001).
14. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.J.A. Montgomery, R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Peterson, P.Y. Ayala, Q. Cui, K. Morokuma, N. Rega, P. Salvador, J.J. Dannenberg, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, and J.A. Pople. Gaussian 98 [computer program]. Revision A.11.4. Gaussian, Inc., Pittsburgh, PA. 2002.
15. P.C. Hariharan and J.A. Pople. Theor. Chim. Acta, 28, 213 (1973).
16. P.C. Hariharan and J.A. Pople. Mol. Phys. 27, 209 (1974).
17. W.J. Hehre, R. Ditchfield, and J.A. Pople. J. Chem. Phys. 56, 2257 (1972).
18. M.S. Gordon. Chem. Phys. Lett. 76, 163 (1980).
19. R. Ditchfield, W.J. Hehre, and J.A. Pople. J. Chem. Phys. 54, 724 (1971).
20. L.G. Sillen. In Coordination chemistry. Vol. 1. Edited by A.E. Martell. Van Nostrand Reinhold, New York. 1971. pp. 481-541.
21. C.F. Baes and R.E. Mesmer. The hydrolysis of cations. Wiley, New York. 1976.
22. G.R.J. Thatcher. In Anomeric effect and associated stereoelectronic effects. Edited by G.R.J. Thatcher. ACS Symposium Series 539. American Chemical Society, Washington, D.C. 1993. pp. 6-25.
23. B.M. Pinto and R.Y.N. Leung: In Anomeric effect and associated stereoelectronic effects. Edited by G.R.J. Thatcher. ACS Symposium Series 539. American Chemical Society, Washington, D.C. 1993. pp. 126-155.
24. R.F.W. Bader. Acc. Chem. Res. 18, 9 (1985).
25. N.H. Werstiuk, K.E. Laidig, and J. Ma. In Anomeric effect and associated stereoelectronic effects. Edited by G.R.J. Thatcher. ACS Symposium Series 539. American Chemical Society, Washington, D.C. 1993. pp. 176-204.
26. G. Madrid, A. Rochin, E. Juaristi, and G. Cuevas. J. Org. Chem. 66, 2925 (2001).
27. A. Vila and R.A. Mosquera. J. Phys. Chem. A, 104, 12 006 (2000).
28. A.E. Reed, L.A. Curtiss, and F. Weinhold. Chem. Rev. 88, 899 (1988).
29. F. Cortes, J. Tenorio, O. Collera, and G. Cuevas. J. Org. Chem. 66, 2918 (2001).
30. L. Carballeira and I. Perez-Juste. J. Comput. Chem. 21, 462 (2000).
31. U. Salzner and P.v.R. Schleyer. J. Am. Chem. Soc. 115, 10 231 (1993).
32. A.E. Reed and F. Weinhold. Israel J. Chem. 31, 277 (1991).
33. A.E. Reed and P.v.R. Schleyer. J. Am. Chem. Soc. 109, 7362 (1987).
34. A.E. Reed and P.v.R. Schleyer. Inorg. Chem. 27, 3969 (1988).
35. G.T. Velde, F.M. Bickelhaupt, E.J. Baerends, C.F. Guerra, S.J.A. Van Gisbergen, J.G. Snijders, and T. Ziegler. J. Comput. Chem. 22, 931 (2001).
36. F.M. Bickelhaupt and E.J. Baerends. In Reviews in computational chemistry. Vol. 15. Edited by K.B. Lipkowitz and D.B. Boyd. Wiley-VCH, New York. 2000. pp. 1-86.
37. G. Frenking, K. Wichmann, N. Frohlich, C. Loschen, M. Lein, J. Frunzke, and V.M. Rayon. Coord. Chem. Rev. 238-239, 55 (2003).
38. F. Grein and P. Deslongchamps. Can. J. Chem. 70, 1562 (1992).
39. F. Grein. In Anomeric effect and associated stereoelectronic effects. Edited by G.R.J. Thatcher. ACS Symposium Series 539. American Chemical Society, Washington, D.C. 1993. pp. 205-226.
40. F. Grein. J. Mol. Struct. (Theochem), 536, 87 (2001).