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Elsevier, Tetrahedron, 31(60), p. 6585-6591

DOI: 10.1016/j.tet.2004.06.003

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Reactivity of the carbon-carbon double bond towards nucleophilic additions. A DFT analysis

This paper is available in a repository.
This paper is available in a repository.

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Abstract

The global and local electrophilicity indexes have been used to characterize the reactivity pattern of the C=C double bond towards nucleophilic addition reactions. A wide family of molecules including ketones, esters, anhydrides, nitriles and nitrocompounds containing appropriate substitution on the C=C double bond have been classified within an unique scale of reactivity. The predictive capability of the theoretical model is tested against a series of benzylidenemalononitriles and substituted alpha-nitrostilbenes.