10.1021/ja0634268.s004
Stephen B. Lee
Stephen B.
Lee
Anthony C. Willis
Anthony C.
Willis
Richard D. Webster
Richard D.
Webster
Synthesis of the Phenoxonium Cation of an α-Tocopherol Model Compound
Crystallized with Non-Nucleophilic [B(C<sub>6</sub>F<sub>5</sub>)<sub>4</sub>]<sup>-</sup> and (CB<sub>11</sub>H<sub>6</sub>Br<sub>6</sub>)<sup>-</sup> Anions
American Chemical Society
2006
quaternary carbon
phenoxonium cation
crystal structures
vitamin E model compound
CB 11H AnionsThe phenoxonium cation
Phenoxonium Cation
phenolic ring
length
bond
2006-07-26 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Synthesis_of_the_Phenoxonium_Cation_of_an_Tocopherol_Model_Compound_Crystallized_with_Non_Nucleophilic_B_C_sub_6_sub_F_sub_5_sub_sub_4_sub_sup_sup_and_CB_sub_11_sub_H_sub_6_sub_Br_sub_6_sub_sup_sup_Anions/3068842
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.