2024-11-29 カーディフ大学
＜関連情報＞
- https://www.cardiff.ac.uk/news/view/2882852-chemistry-textbooks-need-rewriting-after-new-research
- https://pubs.rsc.org/en/content/articlelanding/2024/ob/d4ob01572j
有機分子のアルキル基は誘導的に電子を放出するのではない Alkyl groups in organic molecules are NOT inductively electron-releasing
Mark C. Elliott, Colan E. Hughes, Peter J. Knowles and Benjamin D. Ward
Organic & Biomolecular Chemistry Published:12 Nov 2024
DOI:https://doi.org/10.1039/D4OB01572J
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.
