Artículo
Facelli, J.C.; Orendt, A.M.; Contreras, R.H.; Tufró, M.F.; De Kowalewski, D.G. "Ab initio and 17O NMR studies of the substituent effects on the tautomeric equilibrium in 6-X-1H-2-pyridones" (1992) Journal of Physical Chemistry. 96(20):7895-7898
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Abstract:
17O chemical shifts are found to be highly sensitive probes in the study of keto-enol tautomeric equilibria due to the strong sensitivity of these shifts to the coordination of the oxygen atom. The large shielding effect observed, both experimentally and theoretically, for the carbonyl oxygen atom in 2-pyridone suggests that the carbonyl π-electronic system is undergoing a strong conjugation with the formal C3=C4 double bond and/or the nitrogen lone pair. A Cl or NH2 substitution at position 6 of the pyridine ring shifts the tautomeric equilibrium toward the 2-hydroxypyridine form, while a CH3 substitution results in the keto form being predominant, as is the case in the parent compound. © 1992 American Chemical Society.
Registro:
| Documento: | Artículo |
| Título: | Ab initio and 17O NMR studies of the substituent effects on the tautomeric equilibrium in 6-X-1H-2-pyridones |
| Autor: | Facelli, J.C.; Orendt, A.M.; Contreras, R.H.; Tufró, M.F.; De Kowalewski, D.G. |
| Filiación: | Utah Supercomputing Institute, Department of Chemistry, University of Utah, Salt Lake City, UT 84112, United States Department of Chemistry, University of Utah, Salt Lake City, UT 84112, United States Departmento de Física, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires 1428, Argentina |
| Año: | 1992 |
| Volumen: | 96 |
| Número: | 20 |
| Página de inicio: | 7895 |
| Página de fin: | 7898 |
| Título revista: | Journal of Physical Chemistry |
| ISSN: | 00223654 |
| PDF: | https://bibliotecadigital.exactas.uba.ar/download/paper/paper_00223654_v96_n20_p7895_Facelli.pdf |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223654_v96_n20_p7895_Facelli |
Citas:
---------- APA ----------
Facelli, J.C., Orendt, A.M., Contreras, R.H., Tufró, M.F. & De Kowalewski, D.G. (1992) . Ab initio and 17O NMR studies of the substituent effects on the tautomeric equilibrium in 6-X-1H-2-pyridones. Journal of Physical Chemistry, 96(20), 7895-7898.Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223654_v96_n20_p7895_Facelli [ ]
---------- CHICAGO ----------
Facelli, J.C., Orendt, A.M., Contreras, R.H., Tufró, M.F., De Kowalewski, D.G. "Ab initio and 17O NMR studies of the substituent effects on the tautomeric equilibrium in 6-X-1H-2-pyridones" . Journal of Physical Chemistry 96, no. 20 (1992) : 7895-7898.Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223654_v96_n20_p7895_Facelli [ ]
---------- MLA ----------
Facelli, J.C., Orendt, A.M., Contreras, R.H., Tufró, M.F., De Kowalewski, D.G. "Ab initio and 17O NMR studies of the substituent effects on the tautomeric equilibrium in 6-X-1H-2-pyridones" . Journal of Physical Chemistry, vol. 96, no. 20, 1992, pp. 7895-7898.Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223654_v96_n20_p7895_Facelli [ ]
---------- VANCOUVER ----------
Facelli, J.C., Orendt, A.M., Contreras, R.H., Tufró, M.F., De Kowalewski, D.G. Ab initio and 17O NMR studies of the substituent effects on the tautomeric equilibrium in 6-X-1H-2-pyridones. 1992;96(20):7895-7898.Available from: https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223654_v96_n20_p7895_Facelli [ ]
