Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 8, Pages 3112-3116Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201914386
Keywords
alkanes; C-H functionalization; nucleophilicity; reactivity
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Funding
- MINECO [CTQ2017-82893-C2-1-R, CTQ2015-73693-JIN, CTQ2017-87792-R]
- Red Intecat [CTQ2016-81923-REDC]
- Junta de Andalucia [P12-FQM-1765]
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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.
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