Application of semiempirical method (AM1) to the study of tautomeric equilibria in the gas phase for simple compounds containing the amidine group: 4(5)-substituted imidazoles

Analytica Chimica Acta

Volumn 348, Issue 1-3, 1997, Pages 431-441

  Raczynska E D ^a  

^a WARSAW UNIVERSITY OF LIFE SCIENCES   (Poland)

Author keywords

4(5) Substituted imidazoles and their N methyl derivatives; AM1 calculations; Gas phase tautomeric equilibrium constants; Proton affinities and deprotonation enthalpies; Substituent and solvent effects

Indexed keywords

IMIDAZOLE DERIVATIVE;

ALGORITHM; ANALYTICAL ERROR; CONFERENCE PAPER; DRUG STRUCTURE; ENTHALPY; EQUILIBRIUM CONSTANT; GAS; MOLECULAR DYNAMICS; PRIORITY JOURNAL;

EID: 0042802187     PISSN: 00032670     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0003-2670(97)00098-6     Document Type: Conference Paper

References (21)

1. G. Häfelinger and F.K.H. Kuske, in S. Patai and Z. Rappoport (Eds.), The Chemistry of Amidines and Imidates, vol. 2, Willey and Sons, London, 1991, chap. 1.
2. C.L. Perrin, in S. Patai and Z. Rappoport (Eds.), The Chemistry of Amidines and Imidates, vol. 2, Willey and Sons, London, 1991, chap. 3.
3. J. Elguero, C. Marzin, A.R. Katritzky and P. Linda, The Tautomerism of Heterocycles, Academic Press, New York, 1975; and references cited therein.
4. M. Charton, J. Org. Chem., 30 (1965) 3346.
5. M.J.S. Dewar, E.G. Zoebisch, E.F. Healy and J.J.P. Stewart, J. Am. Chem. Soc., 107 (1985) 3902.
6. M.J.S. Dewar and K.M. Dieter, J. Am. Chem. Soc., 108 (1986) 8075.
7. R.W. Taft, E.D. Raczyńska, P.-C. Maria, I. Leito, W. Lewandowski, R. Kurg, J.-F. Gal, M. Decouzon and F. Anvia, Fresenius' J. Anal. Chem., 355 (1996) 412.
8. E.D. Raczyńska, Pol. J. Chem., 70 (1996) 795.
9. J. Catalán, J.L.G. De Paz, M. Yáñez, R.M. Claramunt, C. López, J. Elguero, F. Anvia, J.H. Quian, M. Taagepera and R.W. Taft, J. Am. Chem. Soc., 112 (1990) 1303.
10. S.G. Lias, J.E. Bartmess, J.L. Holmes, R.D. Levin, J.F. Liebman and W.G. Mallard, J. Phys. Chem. Ref. Data, 17(1988) Supplement 1.
11. M.J. Cook, A.R. Katritzky, M. Taagepera, T.D. Singh and R.W. Taft, J. Am. Chem. Soc., 98 (1976) 6048.
12. R.W. Taft, E.D. Raczyńska, P.-C. Maria, I. Leito, J.-F. Gal, M. Decouzon, T. Drapała and F. Anvia, Pol. J. Chem., 69 (1995) 41.
13. E.J. King, Acid-Base Equilibria, Pergamon Press, Oxford, 1965, pp. 13 and 218.
14. R. Voets and François, J.-P.J.M.L. Martin, J. Mullens, J. Yperman and L.C. Van Poucke, J. Comput. Chem., 10 (1989) 449.
15. B. Nogaj, E. Dulewicz, B. Brycki, A. Hrynio, P. Barczyński, Z. Dega-Szafran, M. Szafran, P. Kozioł and A.R. Katritzky, J. Phys. Chem., 94 (1990) 1279.
16. D.H. Aue and M.T. Bowers, in M.T. Bowers (Ed.), Gas Phase Ion Chemistry, vol. 2, Academic Press, New York, 1979, chap. 9.
17. R.W. Taft, F. Anvia, M. Taagepera, J. Catalán and J. Elguero, J. Am. Chem. Soc., 108 (1986) 3237.
18. E.D. Raczyńska, P.-C. Maria, J.-F. Gal and M. Decouzon, J. Phys. Org. Chem. 7(1994) 725; and references cited therein.
19. D.H. McDaniel and H.C. Brown, J. Org. Chem., 23 (1958) 420.
20. C. Hansch, A. Leo and R.W. Taft, Chem. Rev., 91 (1991) 165.
21. R.W. Taft and R.D. Topsom, Prog. Phys. Org. Chem., 16 (1987) 1.