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RESEARCH PRODUCT

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

Riccardo GavaAna CaballeroBárbara NovergesGregorio AsensioAndrea OlmosMaria BesoraPedro J. PérezFeliu Maseras

subject

Reactivity modelNucleophilicity010402 general chemistryTopology01 natural sciencesCatalysisC-H functionalizationMetalchemistry.chemical_compoundNucleophile23 QuímicaReactivity (chemistry)Alkanechemistry.chemical_classificationC h bond010405 organic chemistryChemistryGeneral MedicineGeneral ChemistryQuantitative model0104 chemical sciencesvisual_artElectrophileAlkanes descriptorsvisual_art.visual_art_mediumCarbene

description

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.

yearjournalcountryeditionlanguage
2020-01-01Angewandte Chemie International Edition
https://doi.org/10.1002/anie.201914386