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On the reduction of 4-oxo-4H-benzopyran-3-carbaldehydes: Global and local electrophilicity patterns

Abstract:

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 pbkp_redicts 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.