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. 2020 Feb 17;59(8):3112-3116.
doi: 10.1002/anie.201914386. Epub 2020 Jan 21.

A Quantitative Model for Alkane Nucleophilicity Based on C-H Bond Structural/Topological Descriptors

Maria Besora  1   2 , Andrea Olmos  3 , Riccardo Gava  4 , Bárbara Noverges  3 , Gregorio Asensio  3 , Ana Caballero  4 , Feliu Maseras  1   2 , Pedro J Pérez  4
Affiliations

A Quantitative Model for Alkane Nucleophilicity Based on C-H Bond Structural/Topological Descriptors

Maria Besora et al. Angew Chem Int Ed Engl. .

Abstract

A first quantitative model for calculating the nucleophilicity of alkanes is described. A statistical treatment was applied to the analysis of the reactivity of 29 different alkane C-H bonds towards in situ generated metal carbene electrophiles. The correlation of the recently reported experimental reactivity with two different sets of descriptors comprising a total of 86 parameters was studied, resulting in the quantitative descriptor-based alkane nucleophilicity (QDEAN) model. This model consists of an equation with only six structural/topological descriptors, and reproduces the relative reactivity of the alkane C-H bonds. This reactivity can be calculated from parameters emerging from the schematic drawing of the alkane and a simple set of sums.

Keywords: C−H functionalization; alkanes; nucleophilicity; reactivity.

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