An ab initio molecular orbital study of the conformational energies of 3-alkyltetrahydro-2H-thiopyrans (tetrahydrothiopyrans, thiacyclohexanes, thianes)

Journal of Molecular Structure: THEOCHEM

Volumn 492, Issue 1-3, 1999, Pages 225-239

  Freeman, F ^a   Phornvoranunt, A ^a   Hehre, W J ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b Wavefunction Inc   (United States)

Author keywords

3 Alkyltetrahydro 2H thiopyrans; Conformational energies; Equatorial preference; Steric interactions

Indexed keywords

CYCLOHEXANE DERIVATIVE; TETRAHYDRO 2H THIOPYRAN DERIVATIVE; TETRAHYDROPYRAN DERIVATIVE; TETRAHYDROTHIOPYRAN DERIVATIVE; THIOPYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CONFORMATION; ENERGY; STEREOSPECIFICITY;

EID: 0033615922     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0166-1280(99)00168-2     Document Type: Article

References (61)

1. E. Juaristi, G. Cuevas, The Anomeric Effect, CRC Press, Ann Arbor, MI, 1995.
2. F. Freeman, J.A. Kasner, M.L. Kasner, W.J. Hehre, J. Mol. Struct. (Theochem) (1999) in press.
3. E.L. Eliel, S.H. Wilen, Stereochemistry of Organic Compounds, Wiley, New York, 1994, Chap. 11.
4. P.W. Rabideau (Ed.), Conformational Analysis of Cyclohexanes, Cyclohexadienes and Related Hydroaromatic Compounds VCH Publishers, New York, 1987.
5. E. Juaristi (Ed.), Conformational Behavior of Six-Membered Rings VCH Publishers, New York, 1995.
6. E. Juaristi, Introduction of Stereochemistry and Conformational Analysis, Wiley, New York, 1991.
7. K. Gundertofte, T. Liljefors, P.-O. Norby, I. Pettersson, J. Comput. Chem. 17 (1996) 429.
8. F. Freeman, W.J. Hehre, unpublished.
9. E.L. Eliel, S.H. Wilen, Stereochemistry of Organic Compounds, Wiley, New York, 1994, Chap. 11, p. 695.
10. F.A. Carey, R.J. Sundberg, Advanced Organic Chemistry, Part A: Structure and Mechanisms, Plenum Press, New York, 1993, p. 133.
11. S.J. Holness, M.L. Kasner, J. Am. Chem. Soc. 77 (1955) 5562.
12. F. Freeman, Z.M. Tsegai, W.J. Hehre, J. Chem. Educ. (1999) in press.
13. U. Salzner, P.v.R. Schleyer, J. Org. Chem. 59 (1994) 2138.
14. H.N. Po, F. Freeman, C. Lee, W.J. Hehre, J. Comput. Chem. 14 (1993) 1376.
15. F. Freeman, C. Lee, W.J. Hehre, H.N. Po, J. Comput. Chem. 18 (1997) 1302.
16. F. Freeman, C. Lee, W.J. Hehre, H.N. Po, J. Comput. Chem. 19 (1998) 1064.
17. F. Freeman, A. Phornvoranunt, W.J. Hehre, J. Phys. Org. Chem. 11 (1998) 831.
18. F. Freeman, A. Phornvoranunt, W.J. Hehre, J. Phys. Org. Chem. 12 (1999) 176.
19. N.L. Allinger, M.J. Hickey, J. Am. Chem. Soc. 97 (1975) 5167.
20. N.L. Allinger, Y. Fan, J. Comput. Chem. 18 (1997) 1827.
21. N.L. Allinger, K.H. Chen, private communication.
22. E. Kleinpeter, in: E. Juaristi (Ed.), Conformational Behavior of Six-Membered Rings, VCH Publishers, New York, 1995, Chap. 6.
23. W. Klyne, V. Prelog, Experientia 16 (1960) 521.
24. K.B. Wiberg, M.A. Murcko, J. Am. Chem. Soc. 110 (1988) 8029.
25. M.A. Murcko, H. Castejon, K.B. Wiberg, J. Phys. Chem. 100 (1996) 16162.
26. P.v.R. Schleyer, J.E. Williams, K.R. Blanchard, J. Am. Chem. Soc. 92 (1970) 2377.
27. J.E. Anderson, in: Conformational analysis of acyclic and alicyclic saturated hydrocarbons, S. Patai, Z. Rappoport (Eds.), The Chemistry of Alkanes and Cycloalkanes, Wiley, New York, 1992, p. 95.
28. A. Bondi, J. Phys. Chem. 68 (1964) 441.
29. L. Pauling, Nature of the Chemical Bond, 3, Cornell University Press, Ithaca, NY, 1960, pp. 260-261.
30. D.M. Proserpio, R. Hoffmann, R.D. Levine, J. Am. Chem. Soc. 113 (1991) 3217.
31. R. Chauvin, J. Phys. Chem. 96 (1992) 9194.
32. M. O'Keeffe, N.B. Brese, J. Am. Chem. Soc. 113 (1991) 3226.
33. T. Halgren, J. Am. Chem. Soc. 114 (1992) 7827.
34. N.L. Allinger, X. Zhou, J. Bergsma, J. Mol. Struct. (Theochem) 312 (1994) 69.
35. F.A. Carey, R.J. Sundberg, Advanced Organic Chemistry, Part A: Structure and Mechanisms, Plenum Press, New York, 1993, pp. 118-124.
36. F.A. Carroll, Perspectives on Structure and Mechanism in Organic Chemistry, Brooks/Cole, New York, 1998, pp. 5-8.
37. A.E. Reed, R.B. Weinstock, F. Weinhold, J. Phys. Chem. 83 (1985) 735.
38. M.J.S. Dewar, E.G. Zoebisch, E.F. Healy, J.J.P. Stewart, J. Am. Chem. Soc. 107 (1985) 3902.
39. P.C. Hariharah, J.A. Pople, Chem. Phys. Lett. 16 (1972) 217.
40. M.M. Francl, W.J. Pietro, W.J. Hehre, J.S. Binkley, M.S. Gordon, D.J. DeFrees, J.A. Pople, J. Chem. Phys. 77 (1982) 3654.
41. W.J. Hehre, L. Radom, P.v.R. Schleyer, J.A. Pople, Ab Initio Molecular Orbital Theory, Wiley, New York, 1986.
42. A.D. Becke, Phys. Rev. A 38 (1988) 3089.
43. J.P. Perdew, Phys. Rev. B 33 (1986) 8822.
44. W.J. Hehre, L. Lou, A Guide to Density Functional Calculations in Spartan, Wavefunction, Inc., Irvine, CA, 1997.
45. R.W. Kitchin, T.B. Malloy Jr., R.L. Cook, J. Mol. Spectrosc. 57 (1975) 179.
46. G. Schultz, A. Kucsman, I. Hargittai, Acta Chem. Scand. Ser. A 42 (1988) 332.
47. B. Ma, J.-H. Lii, H.F. Schaeffer III, N.L. Allinger, J. Am. Chem. Soc. 100 (1996) 8763.
48. G. Barbarella, P. Dembech, A. Garbesi, A. Fava, Org. Magn. Reson. 8 (1976) 469.
49. R.L. Willer, E.L. Eliel, J. Am. Chem. Soc. 99 (1977) 1925.
50. E.L. Eliel, R.L. Willer, J. Am. Chem. Soc. 99 (1977) 1936.
51. H. Booth, J.R. Everett, J. Chem. Soc. Perkin Trans. 2 (1980) 255.
52. R.W. Franck, Tetrahedron 39 (1983) 3251.
53. R.W. Franck, in: E. Juaristi (Ed.), Conformational Behavior of Six-Membered Rings, VCH Publishers, New York, 1995, chap. 5.
54. J.B. Lambert, J. Am. Chem. Soc. 89 (1967) 1836.
55. J.B. Lambert, R.G. Keske, D.K. Weary, J. Am. Chem. Soc. 89 (1967) 5921.
56. D.M. Fatheree, G.L. Deeg, D.B. Matthews, J.G. Russell, Org. Magn. Reson. 18 (1982) 92.
57. E.L. Eliel, S.H. Wilen, Stereochemistry of Organic Compounds, Wiley, New York, 1994, Chap. 11, pp. 743-745.
58. F.G. Riddell, M.J.T. Robinson, Tetrahedron 23 (1967) 3417.
59. E.L. Eliel, M.C. Knoeber, J. Am. Chem. Soc. 90 (1968) 3444.
60. A.J. Jones, E.L. Eliel, D.M. Grant, M.C. Knoeber, W.F. Bailey, J. Am. Chem. Soc. 93 (1971) 4772.
61. E.L. Eliel, Angew. Chem. Int. Ed. Engl. 11 (1972) 739.