Ab initio and DFT study of molecular structure and tautomerism of 2-amino-2-imidazoline, 2-amino-2-oxazoline and 2-amino-2-thiazoline

Chemical Physics Letters

Volumn 336, Issue 1-2, 2001, Pages 156-162

  Remko, Milan ^a   Walsh, O A ^b   Richards, W G ^b  

^a Physics and Informatics   (Slovakia)

^b UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001341723     PISSN: 00092614     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0009-2614(01)00104-X     Document Type: Article

References (35)

1. R.J. Grout, Biological reactions and pharmaceutical uses of imidic acid derivatives, in: S. Patai (Ed.), The Chemistry of Aminidines and Imidates, vol. 1, Wiley, New York, 1975, p. 255.
2. M.E. Wolff, Burger's Medicinal Chemistry and Drug Discovery, vols. 1-5, Wiley, New York, 1996, 1997.
3. Elguero J., Marzin C., Katritzky A.R., Linda P. The Tautomerism of Heterocycles. 1975;Academic Press, New York.
4. E.D. Raczynska, C. Laurence, J. Chem. Res. (S) 1990, p. 338.
5. Taft R.W., Raczynska E.D., Maria P.C., Leito I., Lewandowski W., Kurg R., Gal J.-F., Decouzon M., Anvia F. Fresenius J. Anal. Chem. 355:1996;412.
6. J. Oszczapowicz, Basicity, H-bonding, tautomerism and complex formation of imidic acid derivatives. in: S. Patai, Z. Rappoport (Eds.), The Chemistry of Aminidines and Imidates, Wiley, New York, 1991, vol. 2, p. 623.
7. P.B.M.W.M. Timmermans, R.D. Smith, in: M. Wolff (Ed.), Burger's Medicinal Chemistry and Drug Discovery, fifth ed., Therapeutic Agents, Wiley, New York, 2, 1996, p. 265.
8. Mailard M.C.et al. J. Med. Chem. 41:1998;3048.
9. Worth G.A., King P.M., Richards W.G. Biochim. Biophys. Acta. 993:1989;134.
10. de Vries A.H., Duijnen P.Th.V. Biophys. Chem. 43:1992;139.
11. Caminiti R., Pieretti A., Bencivenni L., Ramondo F., Sanna N. J. Phys. Chem. 100:1996;10928.
12. Raczynska E.D., Taft R.W. Polish J. Chem. 72:1998;1054.
13. Marchand-Geneste M., Carpy A. J. Mol. Struct. Theochem. 465:1999;209.
14. Frisch M.J.et al. GAUSSIAN 98, Revision A.7. 1998;Gaussian Inc, Pittsburgh, PA.
15. Becke A.D. Phys. Rev. A. 38:1988;3038.
16. Becke A.D. J. Chem. Phys. 98:1993;5648.
17. Lee C., Yang W., Paar R.G. Phys. Rev. B. 37:1988;785.
18. Paar R.G., Yang W. Density-Functional Theory of Atoms and Molecules. 1994;Oxford University Press, New York.
19. Neumann R., Nobes R.H., Handy N.C. Mol. Phys. 98:1996;1.
20. Head-Gordon M., Frisch M.J., Pople J.A. Chem Phys. Lett. 153:1988;503.
21. Frisch M.J., Head-Gordon M., Pople J.A. Chem Phys. Lett. 166:1990;275.
22. Frisch M.J., Head-Gordon M., Pople J.A. Chem Phys. Lett. 166:1990;281.
23. Petersson G.A., Al-Laham M.A. J. Chem. Phys. 94:1991;6081.
24. Montgomery J.A., Ochterski J.W., Peterson G.A. J. Chem. Phys. 101:1994;5900.
25. Petersson G.A., Tensfeldt T., Montgomery J.A. J. Chem. Phys. 94:1991;6091.
26. Ochterski J.W., Petersson G.A., Montgomery J.A. J. Chem. Phys. 104:1996;2598.
27. Bondi A. J. Phys. Chem. 68:1964;441.
28. Sieveking H.U., Lüttke W. Justus Liebigs Ann. Chem. 1977;189.
29. Jarry C., Bosc J.J., Ouhabi J., Carpy A. Arch. Pharm. (Weinheim). 323:1990;157.
30. Ochterski J.W., Petersson G.A., Montgomery J.A. Jr. J. Chem. Phys. 104:1996;2598.
31. Remko M. Phys. Chem. Chem. Phys. 2:2000;1113.
32. E.D. Glendening, A.E. Reed, J.E. Carpenter, F. Weinhold, NBO Version 3.1.
33. Forfar I., Jarry C., Fayet J.P., Carpy A. Arch. Pharm. (Weinheim). 325:1992;541.
34. Pigenet C., Lumbroso H. Bull. Soc. Chem. France. 1972;3401.
35. Wong M.W., Frisch M.J., Wiberg K.B. J. Am. Chem. Soc. 113:1991;4776.