1,3-Diaxial steric effects and intramolecular hydrogen bonding in the conformational equilibria of new cis-1,3-disubstituted cyclohexanes using low temperature NMR spectra and theoretical calculations

Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy

Volumn 62, Issue 1-3, 2005, Pages 30-37

  De Oliveira, Paulo R ^a   Rittner, Roberto ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

1,3 Disubstituted cyclohexanes; Conformational analysis; Low temperature NMR; Theoretical calculations; Vicinal coupling constants

Indexed keywords

CONFORMATIONS; CRYOGENICS; HYDROGEN BONDS; ISOMERS; PARAFFINS; THERMAL EFFECTS;

1,3-DISUBSTITUTED CYCLOHEXANE; CONFORMATIONAL ANALYSIS; LOW TEMPERATURE NMR; THEORETICAL CALCULATIONS; VICINAL COUPLING CONSTAST;

NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

CYCLOHEXANE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; HYDROGEN BOND; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; THERMODYNAMICS;

CYCLOHEXANES; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; THERMODYNAMICS;

EID: 27644463064     PISSN: 13861425     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.saa.2004.12.001     Document Type: Article

References (33)

1. E.L. Eliel, S.H. Wilen, and L.N. Mander Stereochemistry of Organic Compounds 1994 Wiley New York p. 690 and references therein
2. K.B. Wiberg, J.D. Hammer, H. Castejon, W.F. Bailey, E.L. Deleron, and R.M. Jarret J. Org. Chem. 64 1999 2085 2095
3. D. Kost, N. Peor, G.S. Moriah, Y. Sharabi, D.T. Durocher, and M. Raban J. Org. Chem. 67 2002 6938 6943
4. M.P. Freitas, C.F. Tormena, P.R. Oliveira, and R. Rittner J. Mol. Struct. (Theochem.) 589 2002 147 151
5. E.J. Corey, and N.F. Feiner J. Org. Chem. 45 1980 765 780
6. B. Franzus, and B.E. Hudson J. Org. Chem. 28 1963 2238 2244
7. P.R. Oliveira, and R. Rittner Spectrochim. Acta, Part A 61 2005 1737 1745
8. P.R. Oliveira, D.S. Ribeiro, and R. Rittner J. Phys. Org. Chem. 17 2004
9. B.S. Furniss, A.J. Hannford, V. Rogers, P.W.G. Smith, and A.R. Tatchell Vogel's Textbook of Practical Organic Chemistry 1978 Longman London
10. S. Nishimura, H. Uchino, and H. Yoshino Bull. Chem. Soc. Jpn. 41 1968 2194 2195
11. E.A. Basso, P.R. Oliveira, J. Caetano, and I.T.A. Schuquel J. Braz. Chem. Soc. 12 2001 215 222
12. N.S. Zefirov, L.G. Gurvich, A.S. Shashkov, M.Z. Krimer, and E.A. Vorob'eva Tetrahedron 32 1976 1211 1219
13. R.J. Abraham, N. Aboitiz, J. Merrett, B. Sherborne, and I. Whitcombe J. Chem. Soc., Perkin Trans. 2 2000 2382 2392
14. R.J. Abraham, E.J. Chambers, and W.A. Thomas J. Chem. Soc., Perkin Trans. 2 1993 1061 1066
15. R.J. Abraham, T.A.D. Smith, and W.A. Thomas J. Chem. Soc., Perkin Trans. 2 1996 1949 1955
16. PCModel, Version 7, Serena Software, Bloomington, IN, USA, 2001.
17. C.A.G. Haasnoot, F.A.A.M. Leeuw, and C. Altona Tetrahedron 36 1980 2783 2792
18. M. Karplus J. Chem. Phys. 1959 30 31
19. M. Karplus J. Am. Chem. Soc. 85 1963 2870 2871
20. M. Charton Top. Curr. Chem. 114 1983 57 91
21. E.L. Eliel, S.H. Schroeter, T.J. Brett, F.J. Biros, and J.C. Richer J. Am. Chem. Soc. 88 1966 3327 3334
22. D.E. Bugay, C.H. Bushweller, C.T. Danehey, S. Hoogasian, J.A. Blersch, and W.R. Leenstra J. Phys. Chem. 93 1989 3908 3911
23. K.B. Wiberg, J.D. Hammer, H. Castejon, W.F. Bailey, E.L. Deleron, and R.M. Jarret J. Org. Chem. 64 1999 2085 2095
24. H. Booth, and M.L. Jozefowicz J. Chem. Soc., Perkin Trans. 2 1976 895 901
25. F.R. Jensen, C.H. Bushweller, and B.H. Beck J. Am. Chem. Soc. 91 1969 344 351
26. H.J. Schneider, and V. Hoppen J. Org. Chem. 43 1978 3866 3873
27. M.J. Frisch, G.W. Trucks, H.B. Schlegel, J.R. Cheeseman, P.M.W. Gill, M.W. Wong, J.B. Foresman, B.G. Johnson, M.A. Robb, E.S. Replogle, R. Gomperts, J.L. Andres, K. Raghavachavi, J.S. Blinkley, C. Gonzalez, R.L. Martin, D.J. Fox, D.J. Defrees, J. Baker, J.P. Stewart, T. Keith, G.A. Peterson, J.A. Montgomery, M.A. Al-Laham, V.G. Zakrzewski, J.V. Ortiz, J. Cioslowski, B.B. Stefanov, A. Nanayakkara, M. Challacombe, C.Y. Peng, P.Y. Ayala, W. Chen, M. Head-Gordon, and J.A. Pople Gaussian 98, Revision A.7 1998 Gaussian, Inc. Pittsburgh, PA
28. J.B. Foresman, and A. Frish Exploring Chemistry with Electronic Structure Methods 1996 Gaussian, Inc. Pittsburgh, PA
29. P. George, C.W. Bock, and M. Trachtman J. Mol. Struct. (Theochem.) 133 1985 11 24
30. J.S. Craw, and G.B. Bacskay J. Chem. Soc., Faraday Trans. 88 1992 2315 2321
31. T. Schaefer, R. Sebastian, D.M. Mckinnon, P.W. Spevack, K.J. Cox, and C.S. Takeucki Can. J. Chem. 71 1993 960 967
32. A. Simperler, and W. Mikenda Monatsh. Chem. 128 1997 969 980
33. H. Lampert, W. Mikenda, and A. Karpfen J. Phys. Chem. 100 1996 7418 7425