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On a possible catalytic effect of water on some nucleophilic substitution reactions in “Inert” solvents

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Abstract

Ab initio SCF MO LCAO calculations with the 4-31G basis set on the ten most stable complexes involving H2O, HF, HC1, F− and Cl− have been examined in order to verify whether there is some evidence supporting the hypothesis that water can act as a catalyst for some nucleophilic substitution reactions performed in inert solvents with hydrogen halides as nucleophile agents (e.g. the formation of halohydrins from epoxides). Energetic considerations and an analysis of the electrostatic contribution to the reactivity of the H2O-HX adduct seem to support this hypothesis.

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Authors and Affiliations

  1. Laboratorio di Chimica Quantistica ed Energetica Molecolare del C.N.R., Via Risorgimento, 35, I-56100, Pisa, Italy

    Giuliano Alagona, Eolo Scrocco & Jacopo Tomasi

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  1. Giuliano Alagona
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  2. Eolo Scrocco
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  3. Jacopo Tomasi
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Alagona, G., Scrocco, E. & Tomasi, J. On a possible catalytic effect of water on some nucleophilic substitution reactions in “Inert” solvents. Theoret. Chim. Acta 47, 133–145 (1978). https://doi.org/10.1007/BF00547749

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  • DOI: https://doi.org/10.1007/BF00547749

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