Semiempirical (AM1) studies of gas-phase basicity and acidity of simple cyclic nitrogen compounds: Imidazole, 1-, 2- and 4(5)-methylimidazoles. Structural effects: Isomerism and tautomerism

Polish Journal of Chemistry

Volumn 70, Issue 6, 1996, Pages 795-808

  Raczynska E D ^a  

^a WARSAW UNIVERSITY OF LIFE SCIENCES   (Poland)

Author keywords

AM1 calculations; Gas phase basicity and acidity; Imidazole; Methylimidazoles; Structural effects; Tautomerism

Indexed keywords

EID: 0030556843     PISSN: 01375083     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (12)

1. Bell R.P., "The Proton in Chemistry", Chapman and Hall, London 1973.
2. Taft R.W., in "Proton-Transfer Reactions", Eds. Caldin E. and Gold V., Chapman and Hall, London 1975, ch. 2.
3. Taft R.W., Prog. Phys. Org. Chem., 14, 247 (1983).
4. Taft R.W. and Topsom R.D., Prog. Phys. Org. Chem., 16, 1 (1987).
5. Gal J.-F. and Maria P.-C., Prog. Phys. Org. Chem., 17, 159 (1990).
6. Joule J.A. and Smith G.F., "Heterocyclic Chemistry", Van Nostrand Reinhold Company, New York 1978 (tlum. polskie PWN, Warszawa 1984).
7. Lias S.G., Liebman J.F. and Levin R.D., J. Phys. Chem. Ref Data, 13, 695 (1984).
8. Lias S.G., Bartmess J.E., Holmes J.L., Levin R.D., Liebman J.F. and Mallard W.G., J. Phys. Chem. Ref. Data, 17, Supplement 1 (1988).
9. Catalán J., de Paz J.L.G., Yáňez M., Claramunt R.M., López C., Elguero J., Anvia F., Quian J.H., Taagepera M. and Taft R.W., J. Am. Chem. Soc., 112, 1303 (1990).
10. Chen L.-Z., Flammang R., Maquestian A., Taft R.W., Catalán J., Cabildo P., Claramunt R.M. and Elguero J., J. Org. Chem., 56, 179 (1991).
11. Smith B.J. and Radom L., J. Am. Chem. Soc., 115, 4885 (1993).
12. Szulejko J.E. and McMahon T.B., J. Am. Chem. Soc., 115, 7839 (1993).