Alkyl groups in organic molecules are NOT inductively electron-releasing

Elliott, Mark ORCID: https://orcid.org/0000-0003-0132-0818, Hughes, Colan E., Knowles, Peter James ORCID: https://orcid.org/0000-0003-4657-6331 and Ward, Benjamin D. ORCID: https://orcid.org/0000-0003-1406-5940 2024. Alkyl groups in organic molecules are NOT inductively electron-releasing. Organic and Biomolecular Chemistry 10.1039/D4OB01572J

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Abstract

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.

Item Type:	Article
Date Type:	Published Online
Status:	In Press
Schools:	Chemistry
Publisher:	Royal Society of Chemistry
ISSN:	1477-0520
Date of First Compliant Deposit:	12 November 2024
Date of Acceptance:	11 November 2024
Last Modified:	28 Nov 2024 17:00
URI:	https://orca.cardiff.ac.uk/id/eprint/173901

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