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.