Influence of intramolecular hydrogen bonding on the conformational equilibrium of cis-3-N,N-dimethylaminocyclohexanol compared with trans-3-N,N-dimethylaminocyclohexanol and cis- and trans-3-N,N-dimethylamino-1- methoxycyclohexane

Journal of Physical Organic Chemistry

Volumn 18, Issue 6, 2005, Pages 513-521

  De Oliveira, P R ^a   Ribeiro, D S ^a   Rittner, R ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

Conformational analysis; Intramolecular hydrogen bond; NMR spectroscopy; Theoretical calculations

Indexed keywords

AMINES; CONCENTRATION (PROCESS); CONFORMATIONS; DERIVATIVES; HYDROGEN BONDS; ISOMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC SOLVENTS;

CONFORMATIONAL ANALYSIS; COUPLING CONSTANTS; INTRAMOLECULAR HYDROGEN BONDS; THEORETICAL CALCULATIONS;

MOLECULAR DYNAMICS;

EID: 18844426802     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/poc.896     Document Type: Article

References (30)

1. Allan EA, Reeves LW. J. Phys. Chem. 1962; 66: 613-617.
2. Hay RW, Williams PP. J. Chem. Soc. 1964; 2270-2272.
3. Koelle U, Forsen S. Acta Chem. Scand., Ser. A 1974; 28:531-540.
4. Fateley WG, Carlson GL, Bentley FF. J. Phys. Chem. 1975; 79: 199-204.
5. Schaefer T. J. Phys. Chem. 1975; 79: 1888-1890.
6. Pimentel GC, McClelland AL. The Hydrogen Bond. W. H. Freeman: San Francisco, 1960.
7. Finegold H, Kwart H. J. Org. Chem. 1962; 27: 2361-2365.
8. Kuhn LP. J. Am. Chem. Soc. 1952; 74: 2492-2499.
9. Abraham RJ, Smith TAD, Thomas WA. J. Chem. Soc., Perkin Trans. 2 1996; 1949-1955.
10. Eliel EL, Wilen SH, Mander LN. Stereochemistry of Organic Compounds. Wiley: New York, 1994; 690-707.
11. Wiberg KB, Hammer JD, Castejon H, Bailey WF, Deleron EL, Janet RM. J. Org. Chem. 1999; 64: 2085-2095.
12. Basso EA, Oliveira PR, Caetano J, Schuquel ITA. J. Braz. Chem. Soc. 2001; 12: 215-222.
13. Kost D, Peor N, Moriah GS, Sharabi Y, Durocher DT, Raban M. J. Org. Chem. 2002; 67: 6938-6943.
14. Freitas MP, Tormena CF, Oliveira PR, Rittner R. J. Mol. Struct. (Theochem) 2002; 589: 147-151.
15. Corey EJ, Feiner NF. J. Org. Chem. 1980; 45: 765-780.
16. Franzus B, Hudson BE. J. Org. Chem. 1963; 28: 2238-2244.
17. PCModel, Version 75, Serena Software: Bloomington, IN, 2001.
18. Haasnoot CAG, Leeuw FAAM, Altona C. Tetrahedron 1980; 36: 2783-2792.
19. Eliel EL, Schroeter SH. J. Am. Chem. Soc. 1965; 87: 5031-5038.
20. Abraham RJ, Chambers EJ, Thomas WA. J. Chem. Soc., Perkin Trans. 2 1993; 1061-1066.
21. Wypych G. Handbook of Solvents. ChemTec Publishing: Toronto, 2001; 598.
22. Frisch MJ, Trucks GW, Schlegel HB, Cheeseman JR, Gill PMW, Wong MW, Foresman JB, Johnson BG, Robb MA, Replogle ES, Gomperts R, Andres JL, Raghavachavi K, Blinkley JS, Gonzalez C, Martin RL, Fox DJ, Defrees DJ, Baker J, Stewart JP, Keith T, Peterson GA, Montgomery JA, Al-Laham MA, Zakrzewski VG, Ortiz JV, Cioslowski J, Stefanov BB, Nanayakkara A, Challacombe M, Peng CY, Ayala PY, Chen W, Head-Gordon M, Pople JA, Gaussian 98, Revision A.7. Gaussian: Pittsburgh, PA, 1998.
23. Foresman JB, Frish A. Exploring Chemistry with Electronic Structure Methods. Gaussian: Pittsburgh, PA, 1996.
24. George P, Bock CW, Trachtman M. J. Mol. Struct. (Theochem) 1985:133: 11-24.
25. Craw JS, Bacskay GB. J. Chem. Soc., Faraday Trans. 1992; 88: 2315-2321.
26. Schaefer T, Sebastian R, McKinnon DM, Spevack PW, Cox KJ, Takeucki CS. Can. J. Chem. 1993; 71: 960-967.
27. Simperler A, Mikenda W. Monatsh. Chem. 1997; 128; 969-980.
28. Lampert H, Mikenda W, Karpfen A. J. Phys. Chem. 1996; 100: 7418-7425.
29. Millefiori S, Di Bella S. J. Chem. Soc., Faraday Trans. 1991; 87: 1297-1302.
30. Nishimura S, Uchino H, Yoshino H. Bull. Chem. Soc. Jpn. 1968; 41: 2194.