Proportions of species observed in jet spectroscopy-vibrational-energy effects: Histamine tautomers and conformers

Journal of the American Chemical Society

Volumn 120, Issue 41, 1998, Pages 10724-10732

  Godfrey, Peter D ^a   Brown, Ronald D ^a  

^a MONASH UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

HISTAMINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; ISOMERISM; SPECTROSCOPY; STRUCTURE ANALYSIS;

EID: 0032556193     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja980560m     Document Type: Article

References (28)

1. Godfrey, P. D.; Brown, R. D.; Rodgers, F. M. J. Mol. Struct. 1996, 376, 65-81.
2. 3 in that the four species identified experimentally were among the five lowest energy species as predicted by both RHF/3-21G and RHF/6-31G ab initio calculations.
3. Ganellin, C. R.; Pepper, E. S.; Port, G. N. J.; Richards, W. G. J. Med. Chem. 1973, 16, 610-616; Ham, N. S.; Casy, A. F.; Ison, R. R. J. Med. Chem. 1973, 16, 470-475; Byrn, S. R.; Graber, C. W.; Midland, S. L. J. Org. Chem. 1976, 41, 2283-2288; Reynolds, W. F.; Tzeng, C. W. Can. J. Biochem. 1977, 55, 576-578; Wasylishen, R. E.; Tomlinson, G. Can. J. Biochem. 1977, 55, 579-582.
4. Ganellin, C. R.; Pepper, E. S.; Port, G. N. J.; Richards, W. G. J. Med. Chem. 1973, 16, 610-616; Ham, N. S.; Casy, A. F.; Ison, R. R. J. Med. Chem. 1973, 16, 470-475; Byrn, S. R.; Graber, C. W.; Midland, S. L. J. Org. Chem. 1976, 41, 2283-2288; Reynolds, W. F.; Tzeng, C. W. Can. J. Biochem. 1977, 55, 576-578; Wasylishen, R. E.; Tomlinson, G. Can. J. Biochem. 1977, 55, 579-582.
5. Ganellin, C. R.; Pepper, E. S.; Port, G. N. J.; Richards, W. G. J. Med. Chem. 1973, 16, 610-616; Ham, N. S.; Casy, A. F.; Ison, R. R. J. Med. Chem. 1973, 16, 470-475; Byrn, S. R.; Graber, C. W.; Midland, S. L. J. Org. Chem. 1976, 41, 2283-2288; Reynolds, W. F.; Tzeng, C. W. Can. J. Biochem. 1977, 55, 576-578; Wasylishen, R. E.; Tomlinson, G. Can. J. Biochem. 1977, 55, 579-582.
6. Ganellin, C. R.; Pepper, E. S.; Port, G. N. J.; Richards, W. G. J. Med. Chem. 1973, 16, 610-616; Ham, N. S.; Casy, A. F.; Ison, R. R. J. Med. Chem. 1973, 16, 470-475; Byrn, S. R.; Graber, C. W.; Midland, S. L. J. Org. Chem. 1976, 41, 2283-2288; Reynolds, W. F.; Tzeng, C. W. Can. J. Biochem. 1977, 55, 576-578; Wasylishen, R. E.; Tomlinson, G. Can. J. Biochem. 1977, 55, 579-582.
7. Ganellin, C. R.; Pepper, E. S.; Port, G. N. J.; Richards, W. G. J. Med. Chem. 1973, 16, 610-616; Ham, N. S.; Casy, A. F.; Ison, R. R. J. Med. Chem. 1973, 16, 470-475; Byrn, S. R.; Graber, C. W.; Midland, S. L. J. Org. Chem. 1976, 41, 2283-2288; Reynolds, W. F.; Tzeng, C. W. Can. J. Biochem. 1977, 55, 576-578; Wasylishen, R. E.; Tomlinson, G. Can. J. Biochem. 1977, 55, 579-582.
8. Bonnet, J. J.; Ibers, J. A. J. Am. Chem. Soc. 1973, 95, 4829-4833.
9. Vogelsanger, B.; Godfrey, P. D.; Brown, R. D. J. Am. Chem. Soc. 1991, 113, 7864-7869.
10. Kang, S.; Chou, D. Chem. Phys. Lett. 1975, 34, 537-541; Topiol, S.; Weinstein, H.; Osman, R. J. Med. Chem. 1984, 27, 1531-1534; Gresh, N.; Claverie, P.; Pullman, A, Theor. Chim. Acta 1984, 66, 1-20; Smeyers, Y. G.; Romero-Sanchez, F. J.; Hernandez-Laguna, A. J. Mol. Struct. 1985, 123, 431-442; 1990, 207, 157-167; Topiol, S. J. Comput. Chem. 1987, 8, 142-148.
11. Kang, S.; Chou, D. Chem. Phys. Lett. 1975, 34, 537-541; Topiol, S.; Weinstein, H.; Osman, R. J. Med. Chem. 1984, 27, 1531-1534; Gresh, N.; Claverie, P.; Pullman, A, Theor. Chim. Acta 1984, 66, 1-20; Smeyers, Y. G.; Romero-Sanchez, F. J.; Hernandez-Laguna, A. J. Mol. Struct. 1985, 123, 431-442; 1990, 207, 157-167; Topiol, S. J. Comput. Chem. 1987, 8, 142-148.
12. Kang, S.; Chou, D. Chem. Phys. Lett. 1975, 34, 537-541; Topiol, S.; Weinstein, H.; Osman, R. J. Med. Chem. 1984, 27, 1531-1534; Gresh, N.; Claverie, P.; Pullman, A, Theor. Chim. Acta 1984, 66, 1-20; Smeyers, Y. G.; Romero-Sanchez, F. J.; Hernandez-Laguna, A. J. Mol. Struct. 1985, 123, 431-442; 1990, 207, 157-167; Topiol, S. J. Comput. Chem. 1987, 8, 142-148.
13. Kang, S.; Chou, D. Chem. Phys. Lett. 1975, 34, 537-541; Topiol, S.; Weinstein, H.; Osman, R. J. Med. Chem. 1984, 27, 1531-1534; Gresh, N.; Claverie, P.; Pullman, A, Theor. Chim. Acta 1984, 66, 1-20; Smeyers, Y. G.; Romero-Sanchez, F. J.; Hernandez-Laguna, A. J. Mol. Struct. 1985, 123, 431-442; 1990, 207, 157-167; Topiol, S. J. Comput. Chem. 1987, 8, 142-148.
14. Kang, S.; Chou, D. Chem. Phys. Lett. 1975, 34, 537-541; Topiol, S.; Weinstein, H.; Osman, R. J. Med. Chem. 1984, 27, 1531-1534; Gresh, N.; Claverie, P.; Pullman, A, Theor. Chim. Acta 1984, 66, 1-20; Smeyers, Y. G.; Romero-Sanchez, F. J.; Hernandez-Laguna, A. J. Mol. Struct. 1985, 123, 431-442; 1990, 207, 157-167; Topiol, S. J. Comput. Chem. 1987, 8, 142-148.
15. Kang, S.; Chou, D. Chem. Phys. Lett. 1975, 34, 537-541; Topiol, S.; Weinstein, H.; Osman, R. J. Med. Chem. 1984, 27, 1531-1534; Gresh, N.; Claverie, P.; Pullman, A, Theor. Chim. Acta 1984, 66, 1-20; Smeyers, Y. G.; Romero-Sanchez, F. J.; Hernandez-Laguna, A. J. Mol. Struct. 1985, 123, 431-442; 1990, 207, 157-167; Topiol, S. J. Comput. Chem. 1987, 8, 142-148.
16. (3) to designate the tautomers, or sometimes just 1 or 3 when different conformers are being discussed.
17. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986; p 294.
18. Pople, J. A.; Head-Gordon, M.; Fox, D. J.; Raghavachari, K.; Curtiss, L. A. J. Chem. Phys. 1989, 90, 5622.
19. Godfrey, P. D.; Rodgers, F. M.; Brown, R. D. J. Am. Chem. Soc. 1997, 119, 2232-2239.
20. Nagy, P. I.; Durant, G. J.; Hoss, W. P.; Smith, D. A. J. Am. Chem. Soc. 1994, 116, 4898-4909.
21. Gaussian 94, Revision B.1, Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian, Inc.: Pittsburgh, PA, 1995.
22. Nagy, P. I.; Durant, G. J.; Hoss, W. P.; Smith, D. A. J. Am. Chem. Soc. 1993, 115, 2912-2922.
23. Brown, R. D.; Crofts, J. G.; Godfrey, P. D.; McNaughton, D.; Pierlot, A. P. J. Mol. Struct. 1988, 190, 185-193.
24. Blackman, G. L.; Bolton, K.; Brown, R. D.; Burden, F. R.; Mishra, A. J. Mol. Spectrosc. 1973, 47, 457-468. Modernized and improved by P. D. Godfrey.
25. See, for example, Herzberg, G. Infrared and Raman Spectra of Polyatomic Molecules; D. Van Nostrand: 1945, Chapter 5.
26. Scuseria, G. E.; Schaefer, H. F. J. Chem. Phys. 1987, 87, 4020-4024.
27. Brown, R. D.; Head-Gordon, M. P. Mol. Phys. 1987, 61, 1183-1191.
28. Gai, F.; Hasson, K. C.; McDonald, J. C.; Anfinrud, P. A. Science 1998, 279, 1886-1891.