Redox potentials of trifluoromethyl-containing compounds
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- 作者：Yuanye Jiang (1)
Haizhu Yu (2) (3)
Yao Fu (1)
Lei Liu (3)
1. Department of Chemistry ; University of Science and Technology of China ; Hefei ; 230026 ; China
2. Department of Polymer Science and Engineering ; University of Science and Technology Beijing ; Beijing ; 100083 ; China
3. Department of Chemistry ; Tsinghua University ; Beijing ; 100084 ; China - 关键词：trifluoromethylation ; redox potential ; density functional theory
- 刊名：SCIENCE CHINA Chemistry
- 出版年：2015
- 出版时间：April 2015
- 年：2015
- 卷：58
- 期：4
- 页码：673-683
- 全文大小：956 KB
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- 刊物主题：Chemistry
Chinese Library of Science
Chemistry - 出版者：Science China Press, co-published with Springer
- ISSN：1869-1870
文摘
Trifluoromethylation reactions are important transformations in the research and development of drugs, agrochemicals and functional materials. An oxidation/reduction process of trifluoromethyl-containing compounds is thought to be involved in many recently tested catalytic trifluoromethylation reactions. To provide helpful physical chemical data for mechanistic studies on trifluoromethylation reactions, the redox potentials of a variety of trifluoromethyl-containing compounds and trifluoromethylated radicals were studied by quantum-chemical methods. First, wB97X-D was found to be a reliable method in predicting the ionization potentials, electron affinities, bond dissociation enthalpies and redox potentials of trifluoromethyl-containing compounds. One-electron absolute redox potentials of 79 trifluoromethyl substrates and 107 trifluoromethylated radicals in acetonitrile were then calculated with this method. The theoretical results were found to be helpful for interpreting experimental observations such as the relative reaction efficiency of different trifluoromethylation reagents. Finally, the bond dissociation free energies (BDFE) of various compounds were found to have a good linear relationship with the related bond dissociation enthalpies (BDE). Based on this observation, a convenient method was proposed to predict one-electron redox potentials of neutral molecules.