Article Dans Une Revue Journal of Physical Chemistry A Année : 2011

A Density Functional Theory Study of the Nef-Isocyanide Reaction: Mechanism, Influence of Parameters and Scope

Résumé

The Nef reaction between isocyanides and acyl chlorides is studied at the M06-2X/6-311+G(d,p) level of theory in toluene. After proving that the reaction follows a concerted mechanism instead of an addition–elimination path, we study the influences of the solvent, the isocyanide, the acyl moiety and the leaving group on the energy profile of the reaction. The calculated data can be rationalized with the pKa of the leaving group, or more generally with the population of the oxygen lone pairs of the acyl moiety.

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hal-01664774 , version 1 (24-01-2025)

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Nicolas Chéron, Laurent El Kaim, Laurence Grimaud, Paul Fleurat-Lessard. A Density Functional Theory Study of the Nef-Isocyanide Reaction: Mechanism, Influence of Parameters and Scope. Journal of Physical Chemistry A, 2011, 115 (35), pp.10106 - 10112. ⟨10.1021/jp205909d⟩. ⟨hal-01664774⟩
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