Keto-enol tautomerism, NMR spectra, and H-D exchange of 4-hydroxycoumarins

Canadian Journal of Chemistry

Volumn 75, Issue 4, 1997, Pages 377-383

  Traven, Valery F ^a   Negrebetsky, Vadim V ^a   Vorobjeva, Larisa I ^a   Carberry, Edward Andrew ^b  

^a MENDELEEV UNIVERSITY OF CHEMICAL TECHNOLOGY OF RUSSIA   (Russian Federation)

^b SOUTHWEST MINNESOTA STATE UNIVERSITY   (United States)

Author keywords

4 hydroxycoumarin derivatives; H D exchange; Keto enol tautomerism

Indexed keywords

AROMATIC COMPOUNDS; COMPUTATIONAL METHODS; CONFORMATIONS; DERIVATIVES; HYDROGEN BONDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

HYDROXYCOUMARINS; KETOENOL TAUTOMERISM; TAUTOMERIC TRANSFORMATIONS;

ESTERS;

EID: 0031124841     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v97-043     Document Type: Article

References (38)

1. R.D.H. Murray. The natural coumarins, occurrence, chemistry and biochemistry. Wiley-Interscience, New York. 1982.
2. R.D.H. Murray. Nat. Prod. Rep. 6, 551 (1989).
3. W.G. Levine. In The pharmacological basis of therapeutics. 5th ed. Edited by L.S. Goodman and A. Gilman. MacMillan, New York. 1975.
4. R.A. O'Reilly. Annu. Rev. Med. 27, 245 (1976).
5. R.B. Silverman. J. Am. Chem. Soc. 103, 3910 (1981).
6. F. Arndt, L. Loewe, R. Un, and E. Ayca. Chem. Ber. 84, 319 (1951).
7. H.R. Eisenhauer and K.P. Link. J. Am. Chem. Soc. 75, 2044 (1953).
8. D. Anker and J. Massicot. Bull. Soc. Chim. Fr. 6, 2181 (1969).
9. N. Matzat, H. Wamhoff, and F. Korte. Chem. Ber. 102, 3122 (1969).
10. G. Appendino, G. Cravotto, S. Tagliapietra, and G.M. Nano. Helv. Chim. Acta, 73, 1865 (1990).
11. G. Appendino, G. Cravotto, S. Tagliapietra, S. Ferraro, G.M. Nano, and G. Palmisano. Helv. Chim. Acta, 74, 1451 (1991).
12. G. Appendino, G. Cravotto, L. Toma, R. Annunziata, and G. Palmisano. J. Org. Chem. 59, 5556 (1994).
13. M. Rahman, Kh. Z. Khan, Z. S. Siddigi, and A. Zaman. Indian J. Chem. 29B, 941 (1990).
14. A.S. Shawali, N.M.S. Harb, and K.O. Badahdah. J. Heterocycl. Chem. 22, 1397 (1985).
15. E. Knobloch, B. Kakai, and F. Macha. Chem. Listy, 46, 416 (1952).
16. O.S. Wolfbeis and G. Uray. Monatsh. Chem. 109, 123 (1978).
17. Th. A. Moore, M. L. Harter, and P.-S. Song. J. Mol. Spectrosc. 40, 144 (1971).
18. P.-S. Song. Can. J. Spectrosc. 26, 59 (1981).
19. A.O. Obaseka, W.R. Porter, and W.F. Trager. J. Heterocycl. Chem. 19, 385 (1982).
20. W.R. Porter and W.F. Trager. J. Heterocycl. Chem. 19, 475 (1982).
21. S.A. Cussans and T.N. Huckerbyb. Tetrahedron, 21, 2719 (1975).
22. A. Patra, A.K. Mukhopadhyay, and A.K. Mitra. Ind. J. Chem. 258, 1167 (1986).
23. S.A. Soika. J. Org. Chem. 40, 1175 (1975).
24. P. Ilic, B. Mohar, J.V. Knop, A. Juric, and N. Trinajstic. J. Heterocycl. Chem. 19, 625 (1982).
25. V.R. Shah, J.L. Bose, and R.C. Shah. J. Org. Chem. 25, 677 (1960).
26. G. Jacobson. J. Am. Chem. Soc. 107, 1055 (1985).
27. A. Buckle. J. Med. Chem. 18, 391 (1975).
28. J. Klosa. Arch. Pharm. 288, 356 (1955).
29. M.J.S. Dewar and W. Thiel. J. Am. Chem. Soc. 99, 4907 (1977).
30. M.J.S. Dewar, A.J. Harget, N. Trinajstic, and S.D. Worley. Tetrahedron, 26, 4505 (1970).
31. Atta-ur-Rahman. One and two dimensional NMR spectroscopy. Elsevier, New York. 1989.
32. V.F. Traven, L.I. Vorobjeva, T.A. Chibisova, E.A. Carberry, and N.J. Beyer. Can. J. Chem. 75, 365 (1997).
33. O.A. Reutov, I.P. Belezkaya, and K.P. Butin. The CH-acids. Nauka, Moscow. 1980.
34. H.R. Eisenhauer and K.P. Link. J. Am. Chem. Soc. 76, 1647 (1954).
35. E. Ziegler and H. Maier. Monatsh. Chem. 89, 787 (1958).
36. K. Fukui et al. J. Chem. Phys. 22, 1433 (1954).
37. V.F. Traven. Frontier orbitals and properties of organic molecules. Ellis Horwood, Chichester. 1992.
38. V.P. Georgievskyi. Khim. Prir. Soedin. 6, 770 (1985).