Synthesis of the Phenoxonium Cation of an α-Tocopherol Model Compound Crystallized with Non-Nucleophilic [B(C6F5)4]- and (CB11H6Br6)- Anions
- 29 June 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 128 (29) , 9332-9333
- https://doi.org/10.1021/ja0634268
Abstract
The phenoxonium cation of a vitamin E model compound has been crystallized using the non-nucleophilic carborane and tetrakis(pentafluorophenyl)borate counteranions. The crystal structures confirm the assignment of the unusually stable phenoxonium cation and indicate that there is a substantial shortening of the carbon-oxygen bond lengths of the para-carbon atoms in the phenolic ring and a substantial increase of the carbon-oxygen bond length at the quaternary carbon. The crystallographic data are in excellent agreement with structural predictions from molecular orbital calculations.Keywords
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