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Quantifying electro/nucleophilicity by partitioning the dual descriptor

Abstract : Translating local electro/nucleophilicities into the language of reactive sites is an appealing theoretical challenge that could be conducive to strengthen the collaborative dialogue between experimentalists and quantum chemists. The usual schemes for such condensation, relying on atomic charges, may however lead to important information loss, due to a sometimes inappropriate averaging of the reactivity anisotropy. In this article, we present instead an approach based on the dual descriptor f, which aims at partitioning real space into nonoverlapping reactive domains that feature a constant f sign. This strategy enables not only to identify the nucleo/electrophilic regions inside a molecule but also to quantify meaningful properties (mean value, volume, electron population...). Its interest is then illustrated on two specific chemical problems: the measure of sigma-holes in the context of halogen bonds, and of the electrophilicity of organic carbocations, casting the light on the versatility of this method.
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https://hal.archives-ouvertes.fr/hal-01187097
Contributor : Agnès Bussy <>
Submitted on : Wednesday, August 26, 2015 - 10:23:20 AM
Last modification on : Friday, April 17, 2020 - 2:52:02 PM

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Vincent Tognetti, Christophe Morell, Laurent Joubert. Quantifying electro/nucleophilicity by partitioning the dual descriptor. Journal of Computational Chemistry, Wiley, 2015, 36 (9), pp.649-659. ⟨10.1002/jcc.23840⟩. ⟨hal-01187097⟩

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