Spectroscopic and theoretical investigation of (R)-3-methylcyclopentanone. the effect of solvent and temperature on the distribution of conformers

Journal of Physical Chemistry A

Volumn 111, Issue 12, 2007, Pages 2293-2298

  Al Basheer, Watheq ^a,b   Pagni, Richard M ^a   Compton, Robert N ^a  

^a UNIVERSITY OF TENNESSEE   (United States)

^b HASHEMITE UNIVERSITY   (Jordan)

Author keywords

[No Author keywords available]

Indexed keywords

CONFORMATIONS; DENSITY FUNCTIONAL THEORY; DICHROISM; DIPOLE MOMENT; OPTICAL ROTATION; SOLVENTS; SPECTROSCOPIC ANALYSIS; THERMAL EFFECTS;

CONFORMERS; POLARITY; SOLUTION-PHASE SPECTRA;

KETONES;

EID: 84962428740     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp068320d     Document Type: Article

References (34)

1. Dzakua, Z.; DeRider, M. L.; Markley, J. L. J. Am. Chem. Soc. 1996, 118, 12796.
2. Brutcher, F. V., Jr.; Roberts, T.; Barr, S. J.; Pearson, N. J. Am. Chem. Soc. 1959, 81, 4915.
3. He, J.; Petrovic, A. G.; Polavarapu, P. L. J. Phys. Chem. B 2004, 108, 20451.
4. Boese, R.; Oberhammer, H.; Pulay, P.; Waterfeld, A. J. Phys. Chem. 1993, 38, 9625.
5. Mislow, K.; Bunnenber, E.; Records, R.; Wellman, K.; Djerassi, C. J. Am. Chem. Soc. 1962, 84, 1342.
6. Wellman, K.; Bunnenber, E.; Djerassi, C. J. Am. Chem. Soc. 1963, 85, 1870.
7. Moscowitz, A.; Wellman, K. Djerassi, C. J. Am. Chem. Soc. 1963, 85, 3515.
8. Moscowitz, A.; Wellman, K. Djerassi, C. Proc. Natl. Acad. Sci. 1963, 50, 799.
9. Wellman, K.; Records, R.; Bunnenberg, E.; Djerassi, C. J. Am. Chem. Soc. 1963, 85, 492.
10. Wellman, K.; Djerassi, C. J. Am. Chem. Soc. 1964, 86, 1964.
11. Wellman, K.; Laur, P. H. A.; Briggs, W. S.; Moscowitz, A.; Djerassi, C. J. Am. Chem. Soc. 1965, 87, 66.
12. Wellman, K.; Briggs, W. S.; Djerassi, C. J. Am. Chem. Soc. 1964, 86, 73.
13. Kirk, D. N.; Kyle, W.; Wallis, S. R. J. Chem. Soc. C 1970, 350.
14. Lightner, D. A.; Bouman, T. D.; Wijekoon, W. M. D.; Hansen, A. E. J. Am. Chem. Soc. 1986, 108, 4484.
15. Li Y. S. J. Mol. Spectrosc. 1984, 104, 302.
16. Richardson, F. S.; Shillady, D. D.; Bloor, J. E. J. Phys. Chem. 1971, 75, 2466.
17. Flament, J. P.; Gervais, J. P. Tetrahedron 1980, 36, 1949.
18. Potts, A. R.; Nesselrodt, D. R.; Baer, T.; Driscoll, J. W.; Philip, J. J. Phys. Chem. 1995, 99, 12090.
19. Kim, D.; Baer, T. Chem. Phys. 2000, 256, 251.
20. Li, R.; Sullivan, R.; Al-Basheer, W.; Pagni, R. M.; Compton, R. N. J. Chem. Phys. 1006, 125, 144304.
21. Fischer, A. T.; Compton, R. N.; Pagni, R. M. J. Phys. Chem. A 2006, 110, 7067.
22. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision B.03; Gaussian, Inc.: Pittsburgh, PA, 2003.
23. Ballard, R. E.; Mason, S. F.; Vane, G. W. Discuss. Faraday Soc. 1963, 35, 43.
24. Temperature-dependent CD spectra of R3MCP are shown in ref 20.
25. Jaffé, H.; Orchin, M. Theory and Applications of Ultraviolet Spectroscopy; Wiley: New York, 1962.
26. Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, 117.
27. Miertus, S.; Tomasi, J. Chem. Phys. 1992, 65, 239.
28. Cossi, M.; Barone, V.; Cammi, R.; Tomasi, J. Chem. Phys. Lett. 1996, 255, 327.
29. Djerassi, C.; Warawa, E. J.; Berdahl, J. M.; Eisenbraun, E. J. J. Am. Chem. Soc. 1961, 83, 3334.
30. Robins, P. A.; Walker, J. Chem. Ind. (London) 1955, 772.
31. Lightner, D. A.; Crist, B. V. Appl. Spectrosc. 1979, 33, 3.
32. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry, 3rd ed.; Wiley-VCH: Weinheim, Germany, 2003.
33. Marcus, Y. The Properties of Solvents; 1998.
34. Handbook of Chemistry and Physics, 68th ed.; Lide, D. R., Ed.; CRC Press: Boca Raton, FL, 1987-1988.