有机分子中的烷基不会感应释放电子。

IF 2.9 3区 化学 Q1 CHEMISTRY, ORGANIC Organic & Biomolecular Chemistry Pub Date : 2024-11-15 DOI:10.1039/d4ob01572j
Mark C Elliott, Colan E Hughes, Peter J Knowles, Benjamin D Ward
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引用次数: 0

摘要

一般认为,与氢相比,烷基具有感应电子释放效应。在过去的 75 年中,许多有机化学教科书都给出了这一信息。这一观点的证据不足,经不起推敲,而相反的观点也有一些证据。我们提供了大量的计算数据,这些数据清楚地表明,与氢相比,烷基具有诱导性电子吸收(-I)效应。这一修正立场与实验数据并不冲突,因为烷基的感应效应很小,很可能被超共轭/极化效应(尤其是带电物种)以及溶剂效应所掩盖。
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Alkyl groups in organic molecules are NOT inductively electron-releasing.

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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来源期刊
Organic & Biomolecular Chemistry
Organic & Biomolecular Chemistry 化学-有机化学
CiteScore
5.50
自引率
9.40%
发文量
1056
审稿时长
1.3 months
期刊介绍: The international home of synthetic, physical and biomolecular organic chemistry.
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