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
Handle:http://hdl.handle.net/20.500.12110/paper_00223654_v96_n20_p7895_Facelli
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 [ ]