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Updated: Jun 7, 2025

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents
Published on: November 12, 2016
Alkyl groups in organic molecules are NOT inductively electron-releasing
Mark C Elliott1, Colan E Hughes1, Peter J Knowles1
1School of Chemistry, Cardiff University, Park Place, Cardiff, CF10 3AT, UK. elliottmc@cardiff.ac.uk.
None:
It is commonly stated that alkyl groups exert an inductive electron-releasing effect when compared to hydrogen. This information has been given in numerous organic chemistry textbooks over the last 75 years. The evidence for this position is weak, and does not withstand scrutiny, and there is some evidence for the contrary position. We provide a significant body of computational data that clearly show that alkyl groups exert an inductive electron-withdrawing (-I) effect when compared to hydrogen. This revised position is not in conflict with experimental data, since alkyl group inductive effects are small and are likely to be masked by hyperconjugation/polarizability effects (particularly in charged species), and also by solvent effects.
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