Enantiomeric separation of sulfonium ions by capillary electrophoresis using neutral and charged cyclodextrins

Capillary zone electrophoresis was successfully applied, for the first time, to the chiral separation of structurally related sulfonium ions, using sodium phosphate buffer pH 2.5 with β-cyclodextrin (β-CD) or sulfated-β-cyclodextrin (S-β-CD) as the chiral selector with tetrabutylammonium bromide (TBA). For this study, a series of structurally related sulfonium ions in which one of the alkyl chains varied in length were synthesized from a common sulfide. The resolution of the ions was found to be dependent on the type of cyclodextrin used, the presence or absence of TBA, and the structure of the sulfonium ion. β-CD was found to be effective only for ions containing two aromatic groups, while the S-β-CD was effective only for ions containing one aromatic group. The chiral separation of thiophenium ions was also studied under the conditions established. Chiral separation of sulfonium ions in a binary buffer system containing methanol was explored as well. Separations were achieved for all but one sulfonium ion and one thiophenium ion. The data presented show the effectiveness of the enantiomeric separation using CZE with cyclodextrin-modified buffer for these types of ions.