An experimental comparison of vibrational circular dichroism and Raman optical activity with 1-amino-2-propanol and 2-amino-1-propanol as model compounds

Journal of the American Chemical Society

Volumn 119, Issue 30, 1997, Pages 7061-7064

  Tam, Cheok N ^a,b   Bour, Petr ^a,c   Keiderling, Timothy A ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^b ARGONNE NATIONAL LABORATORY   (United States)

^c INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

PROPANOL; PROPANOLAMINE DERIVATIVE;

ARTICLE; CHIRALITY; CIRCULAR DICHROISM; CONFORMATIONAL TRANSITION; OPTICS; RAMAN SPECTROMETRY; VIBRATION;

EID: 0030875093     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja963239h     Document Type: Article

References (31)

1. Nafie, L. A.; Yu, G.-S.; Qu, X.; Freedman, T. B. Faraday Discuss. 1994, 99, 13.
2. Nafie, L. A.; Che, D. Adv. Chem. Phys. 1994, 85 (Part 3), 105. Barron, L. D. In Raman Spectroscopy: Sixty Years On; Bist, H. D., Durig, J. R., Sullivan, J. F., Eds.; Elsevier Science: Amsterdam, 1989. Barron, L. D. Molecular Light Scattering and Optical Activity; Cambridge University Press: Cambridge, 1983.
3. Nafie, L. A.; Che, D. Adv. Chem. Phys. 1994, 85 (Part 3), 105. Barron, L. D. In Raman Spectroscopy: Sixty Years On; Bist, H. D., Durig, J. R., Sullivan, J. F., Eds.; Elsevier Science: Amsterdam, 1989. Barron, L. D. Molecular Light Scattering and Optical Activity; Cambridge University Press: Cambridge, 1983.
4. Nafie, L. A.; Che, D. Adv. Chem. Phys. 1994, 85 (Part 3), 105. Barron, L. D. In Raman Spectroscopy: Sixty Years On; Bist, H. D., Durig, J. R., Sullivan, J. F., Eds.; Elsevier Science: Amsterdam, 1989. Barron, L. D. Molecular Light Scattering and Optical Activity; Cambridge University Press: Cambridge, 1983.
5. Freedman, T. B.; Nafie, L. A. Adv. Chem. Phys. 1994, 85 (Part 3), 207. Stephens, P. J.; Devlin, F. J.; Ashwar, C. S.; Chabalowski, C. F.; Frisch, M. J. Faraday Discuss. 1994, 99, 103. Rauk, A. In New Developments in Molecular Chirality; Mezey, P. B., Ed.; Kluwer Academic Publisher: Dordrecht, 1991; p 57. Stephens, P. J.; Lowe, M. A. Annu. Rev. Phys. Chem. 1985, 36, 213.
6. Freedman, T. B.; Nafie, L. A. Adv. Chem. Phys. 1994, 85 (Part 3), 207. Stephens, P. J.; Devlin, F. J.; Ashwar, C. S.; Chabalowski, C. F.; Frisch, M. J. Faraday Discuss. 1994, 99, 103. Rauk, A. In New Developments in Molecular Chirality; Mezey, P. B., Ed.; Kluwer Academic Publisher: Dordrecht, 1991; p 57. Stephens, P. J.; Lowe, M. A. Annu. Rev. Phys. Chem. 1985, 36, 213.
7. Freedman, T. B.; Nafie, L. A. Adv. Chem. Phys. 1994, 85 (Part 3), 207. Stephens, P. J.; Devlin, F. J.; Ashwar, C. S.; Chabalowski, C. F.; Frisch, M. J. Faraday Discuss. 1994, 99, 103. Rauk, A. In New Developments in Molecular Chirality; Mezey, P. B., Ed.; Kluwer Academic Publisher: Dordrecht, 1991; p 57. Stephens, P. J.; Lowe, M. A. Annu. Rev. Phys. Chem. 1985, 36, 213.
8. Freedman, T. B.; Nafie, L. A. Adv. Chem. Phys. 1994, 85 (Part 3), 207. Stephens, P. J.; Devlin, F. J.; Ashwar, C. S.; Chabalowski, C. F.; Frisch, M. J. Faraday Discuss. 1994, 99, 103. Rauk, A. In New Developments in Molecular Chirality; Mezey, P. B., Ed.; Kluwer Academic Publisher: Dordrecht, 1991; p 57. Stephens, P. J.; Lowe, M. A. Annu. Rev. Phys. Chem. 1985, 36, 213.
9. Qu, X.; Lee, E.; Yu, G.; Freedman, T. B.; Nafie, L. A. Appl. Spectrosc. 1996, 50, 649.
10. Yu, G.; Freedman, T. B.; Nafie, L. A. J. Roman Spectrosc. 1995, 26, 733.
11. Keiderling, T. A. In Circular Dichroism and the Conformational Analysis of Biomolecules; Fasman, G. D., Ed.; Plenum Press: New York, 1996; pp 555-598.
12. Barron, L. D. In Circular Dichroism and the Conformational Analysis of Biomolecules; Fasman, G. D., Ed.; Plenum Press: New York, 1996; pp 653-695.
13. Qu, X.; Citra, M.; Ragunathan, N.; Freedman, T. B.; Nafie, L. A. Proceedings of the 9th International Conference on Fourier Transform Spectroscopy; SPIE Vol. 2089; 1993; p 142.
14. Keiderling, T. A. In Practical Fourier Transform Spectroscopy; Kirshman, J. R., Ferraro, J. R., Eds.; Academic Press: San Diego. 1990; p 203. Wang, B.; Keiderling, T. A. Appl. Spectrosc. 1995, 49, 1347.
15. Keiderling, T. A. In Practical Fourier Transform Spectroscopy; Kirshman, J. R., Ferraro, J. R., Eds.; Academic Press: San Diego. 1990; p 203. Wang, B.; Keiderling, T. A. Appl. Spectrosc. 1995, 49, 1347.
16. Tam, C. N. Ph.D. Thesis, University of Illinois at Chicago, 1995. Tam, C. N.; Bour, P.; Keiderling, T. A. J. Am. Chem. Soc. 1996, 118, 10285.
17. Tam, C. N. Ph.D. Thesis, University of Illinois at Chicago, 1995. Tam, C. N.; Bour, P.; Keiderling, T. A. J. Am. Chem. Soc. 1996, 118, 10285.
18. All assignments are based on ab initio force field calculations and on group frequencies derived from: Dollish, F. R.; Fateley, W. G.; Bentley, F. F. Characteristic Raman Frequencies of Organic Molecules; Wiley: New York, 1974.
19. Lipp, E. D.; Zimba, C. G.; Nafie, L. A. Chem. Phys. Lett. 1982, 90, 1. Malon, P.; Keiderling, T. A. Appl. Spectrosc. 1988, 42, 32. Wang, B.; Keiderling, T. A. Appl. Spectrosc. 1995, 49, 1347.
20. Lipp, E. D.; Zimba, C. G.; Nafie, L. A. Chem. Phys. Lett. 1982, 90, 1. Malon, P.; Keiderling, T. A. Appl. Spectrosc. 1988, 42, 32. Wang, B.; Keiderling, T. A. Appl. Spectrosc. 1995, 49, 1347.
21. Lipp, E. D.; Zimba, C. G.; Nafie, L. A. Chem. Phys. Lett. 1982, 90, 1. Malon, P.; Keiderling, T. A. Appl. Spectrosc. 1988, 42, 32. Wang, B.; Keiderling, T. A. Appl. Spectrosc. 1995, 49, 1347.
22. Che, D.; Nafie, L. A. Chem. Phys. Lett. 1992, 189, 35.
23. Devlin, F. J.; Finley, J. W.; Stephens, P. J.; Frisch, M. J. J. Phys. Chem. 1995, 99, 16883. Bour, P.; Keiderling, T. A. J. Am. Chem. Soc. 1992, 114, 9100. Freedman, T. B.; Paterlini, M. G.; Lee, N.-S.; Nafie, L. A.; Schwab, J. M.; Ray, T. J. Am. Chem. Soc. 1987, 109, 4727. Lowe, M. A.; Stephens, P. J.; Segal, G. A. Chem. Phys. Lett. 1986, 123, 108. Malon, P.; Keiderling, T. A.; Uang, J.; Chickos, J. S. Chem. Phys. Lett. 1991, 179, 282.
24. Devlin, F. J.; Finley, J. W.; Stephens, P. J.; Frisch, M. J. J. Phys. Chem. 1995, 99, 16883. Bour, P.; Keiderling, T. A. J. Am. Chem. Soc. 1992, 114, 9100. Freedman, T. B.; Paterlini, M. G.; Lee, N.-S.; Nafie, L. A.; Schwab, J. M.; Ray, T. J. Am. Chem. Soc. 1987, 109, 4727. Lowe, M. A.; Stephens, P. J.; Segal, G. A. Chem. Phys. Lett. 1986, 123, 108. Malon, P.; Keiderling, T. A.; Uang, J.; Chickos, J. S. Chem. Phys. Lett. 1991, 179, 282.
25. Devlin, F. J.; Finley, J. W.; Stephens, P. J.; Frisch, M. J. J. Phys. Chem. 1995, 99, 16883. Bour, P.; Keiderling, T. A. J. Am. Chem. Soc. 1992, 114, 9100. Freedman, T. B.; Paterlini, M. G.; Lee, N.-S.; Nafie, L. A.; Schwab, J. M.; Ray, T. J. Am. Chem. Soc. 1987, 109, 4727. Lowe, M. A.; Stephens, P. J.; Segal, G. A. Chem. Phys. Lett. 1986, 123, 108. Malon, P.; Keiderling, T. A.; Uang, J.; Chickos, J. S. Chem. Phys. Lett. 1991, 179, 282.
26. Devlin, F. J.; Finley, J. W.; Stephens, P. J.; Frisch, M. J. J. Phys. Chem. 1995, 99, 16883. Bour, P.; Keiderling, T. A. J. Am. Chem. Soc. 1992, 114, 9100. Freedman, T. B.; Paterlini, M. G.; Lee, N.-S.; Nafie, L. A.; Schwab, J. M.; Ray, T. J. Am. Chem. Soc. 1987, 109, 4727. Lowe, M. A.; Stephens, P. J.; Segal, G. A. Chem. Phys. Lett. 1986, 123, 108. Malon, P.; Keiderling, T. A.; Uang, J.; Chickos, J. S. Chem. Phys. Lett. 1991, 179, 282.
27. Devlin, F. J.; Finley, J. W.; Stephens, P. J.; Frisch, M. J. J. Phys. Chem. 1995, 99, 16883. Bour, P.; Keiderling, T. A. J. Am. Chem. Soc. 1992, 114, 9100. Freedman, T. B.; Paterlini, M. G.; Lee, N.-S.; Nafie, L. A.; Schwab, J. M.; Ray, T. J. Am. Chem. Soc. 1987, 109, 4727. Lowe, M. A.; Stephens, P. J.; Segal, G. A. Chem. Phys. Lett. 1986, 123, 108. Malon, P.; Keiderling, T. A.; Uang, J.; Chickos, J. S. Chem. Phys. Lett. 1991, 179, 282.
28. Bour, P.; Tam, C. N.; Keiderling, T. A.; Shaharuzzaman, M.; Chickos, J. S. J. Phys. Chem. 1996, 100, 15041.
29. Annamalai, A.; Jalkanen, K. J.; Narayanan, U.; Tissot, M.-C.; Keiderling, T. A.; Stephens, P. J. J. Phys. Chem. 1990, 94, 194. Bour, P.; Keiderling, T. A. J. Am. Chem. Soc. 1993, 115, 9602.
30. Annamalai, A.; Jalkanen, K. J.; Narayanan, U.; Tissot, M.-C.; Keiderling, T. A.; Stephens, P. J. J. Phys. Chem. 1990, 94, 194. Bour, P.; Keiderling, T. A. J. Am. Chem. Soc. 1993, 115, 9602.
31. Yu, G.-S.; Che, D.; Freedman, T. B.; Nafie, L. A. Tetrahedron Asym. 1993, 4, 511.