Dynamic NMR study of trans-cyclodecene

Journal of the American Chemical Society

Volumn 118, Issue 50, 1996, Pages 12821-12825

  Pawar, Diwakar M ^a   Noe, Eric A ^a  

^a JACKSON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FREE ENERGY; MOLECULAR DYNAMICS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLEFINS;

AB INITIO CALCULATIONS; TRANS-CYCLOALKENES; TRANS-CYCLODECENE;

HYDROCARBONS;

CYCLOALKENE;

ARTICLE; DRUG STRUCTURE; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE;

EID: 12644296006     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962666s     Document Type: Article

References (23)

1. Blomquist, A. T.; Liu, L. H.; Bohrer, J. C. J. Am. Chem. Soc. 1952, 74, 3643.
2. Cope, A. C.; Ganellin, C. R.; Johnson, Jr., H. W.; Van Auken, T. V.; Winkler, H. J. S. J. Am. Chem. Soc. 1963, 85, 3276.
3. Cope, A. C.; Mehta, A. S. J. Am. Chem. Soc. 1964, 86, 5626.
4. Cope, A. C.; Pawson, B. A. J. Am. Chem. Soc. 1965, 87, 3649.
5. Cope, A. C.; Bauholzer, K.; Keller, H.; Pawson, B. A.; Whang, J. J.; Winkler, H. J. S. J. Am. Chem. Soc. 1965, 87, 3644.
6. Binsch, G.; Roberts, J. D. J. Am. Chem. Soc. 1965, 87, 5157.
7. Saunders, M.; Jimenez-Vazques, H. A. J. Comput. Chem. 1993, 14, 330
8. 7 through the ring has been described: Fanta, P. Private communication to Roberts, J. D. This process is shown in ref 9, p 64. For a description of conformational processes in medium ring cycloalkanes, see ref 10.
9. Noe, E. A. Ph.D. Thesis, California Institute of Technology, Pasadena, CA, 1971.
10. Kolossvary, I. Guida, W. C. J. Am. Chem. Soc. 1993, 115, 2107.
11. Noe, E. A.; Wheland, R. C.; Glazer, E. S.; Roberts, J. D. J. Am. Chem. Soc. 1972, 94, 3488.
12. a and A values.
13. Levy, G. C.; Lichter, R. L.; Nelson, G. L. Carbon-13 Nuclear Magnetic Resonance Spectroscopy, 2nd ed.; John Wiley & Sons: New York, 1980; p 79.
14. Craig, L. C.; Craig, D. Techniques of Organic Chemistry; Weissberger, A., Ed.; Interscience Publishers, Inc.: New York, NY, 1950; Vol. III, p 171.
15. 1: Traficante, D. D. Concepts Magn. Reson. 1992, 4, 153. See, also: Traficante, D. D.; Steward, L. R. Concepts Magn. Reson. 1994, 6, 131.
16. 1: Traficante, D. D. Concepts Magn. Reson. 1992, 4, 153. See, also: Traficante, D. D.; Steward, L. R. Concepts Magn. Reson. 1994, 6, 131.
17. Frisch, M. J.; Trucks, G. W.; Head-Gordon, M.; Gill, P. M. W.; Wong, M. W.; Foresman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M.; Replogle, E. S.; Gomperts, R.; Anders, J. L.; Raghavaehari, K.; Binkley, J. S.; Gonzales, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. GAUSSIAN 92, Revision A; Gaussian, Inc.: Pittsburgh, PA, 1992.
18. 2 symmetry, but coincidence for all five pairs of carbons is not expected.
19. Peaks 4, 5, and 6 were integrated together. Peak 4 was assumed to have the same area as peak 7, and the area of 5 + 6 was obtained by subtracting this amount.
20. Our version of Spartan does not allow calculation of free energies and populations. We thank Professor Saunders and Mr. Jimenez-Vazquez for sending a complete set of computations for 1.
21. Ganis, P.; Dunitz, J. D. Helv. Chim. Acta 1967, 50, 2379.
22. Calculated spectra were obtained using program DNMR-SIM, written by Hagele, G. and Fuhler, R., Heinrich-Heine University, Dusseldorf Institute of Inorganic and Structural Chemistry, Dusseldorf, FRG, 1994. We thank Mr. Ali Jabalameli of our department for acquiring this program from the internet and for installing the program on our computer.
23. Ring conformations similar to 1c or 1d have been determined for the silver-nitrate adducts of several ten-membered ring sesquiterpenes: McClure, R. J.; Sim, G. A.; Coggon, P.; McPhail, A. T. Chem. Commun. 1970, 128.