On the reduction of 4-oxo-4h-benzopyran-3-carbaldehydes : global and local electrophilicity patterns
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Fecha
2004
Profesor/a Guía
Facultad/escuela
Idioma
en
Título de la revista
ISSN de la revista
Título del volumen
Editor
Sociedad Chilena de Química
Nombre de Curso
Licencia CC
Licencia CC
Resumen
The theoretical global and local electrophilicity patterns of substituted and chelated
4-oxo-4H-benzopyran-3-carbaldehydes (formylchromones) have been evaluated using the electrophilicity
index proposed by Parr et al [J. Am. Chem. Soc. 1999, 121, 1922]. The complexation of formylchromones
with aluminum predicts a strong electrophilic character of these compounds against nucleophiles.
Local response at the active sites may also be assessed in terms of a global contribution described by
the global electrophilicity, and a local contribution described by the variations in electrophilic
Fukui function at those sites. The highest local electrophilicity is found at the formyl group of
the chelated formylchromones, in spite of that, the highest positive charge is located on the pyrone
carbonyl group. This result is consistent with the experimental observed reactivity displayed by
4-oxo-4H-benzopyran-3-carbaldehydes in the presence of 2-propanol and alumina.
Notas
Palabras clave
Benzopyran, Carbaldehydes, Electrophilicity
Citación
Journal of the Chilean Chemical Society, vol. 49, n°1, 2004.