• Bulletin of the Korean Chemical Society
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• v.24 no.7
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• pp.911-915
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• 2003

Two liquid chromatographic chiral stationary phases (CSPs) based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid were successfully applied in the resolution of racemic tocainide and its analogues. In the resolution of tocainide, especially, the CSP containing N-CH₃ amide tethering groups was quite effective, showing clear baseline resolution (RS: 2.66) with reasonable enantioselectivity ( a: 1.25). Consequently, the CSP containing N-CH₃ amide tethering groups is expected to be useful to monitor the enantiomeric composition of tocainide in clinical samples. In addition, the chromatographic behaviors for the resolution of tocainide and its analogues on the two CSPs were found controllable by varying the content and the type of organic and acidic modifiers in aqueous mobile phase.

• Bulletin of the Korean Chemical Society
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• v.31 no.3
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• pp.678-682
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• 2010

A doubly tethered chiral stationary phase (CSP) based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid were applied to the liquid chromatographic resolution of racemic tocainide, an antiarrhythmic agent, and its analogues. The chiral recognition efficiency of the doubly tethered CSP for tocainide and its analogues was generally greater than that of the corresponding singly tethered CSP especially in terms of the resolution ($R_S$). The resolution of tocainide and its analogues on the doubly tethered CSP were dependent on the content and the type of the organic and acidic modifiers in aqueous mobile phase and the column temperature. Especially, the retention behaviors of analytes on the doubly tethered CSP with the variation of the content of organic modifier in aqueous mobile phase were opposite to those on the corresponding singly tethered CSP and these opposite retention behaviors were rationalized by the lipophilicity differences of the two CSPs.

• Bulletin of the Korean Chemical Society
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• v.34 no.10
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• pp.2978-2982
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• 2013

A doubly tethered $N-CH_3$ amide chiral stationary phase (CSP 4) based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid was applied to the resolution of an antiarrythmic agent, tocainide, and its analogues and the chromatographic resolution results were compared with those on a singly tethered N-H amide CSP (CSP 1), a singly tethered $N-CH_3$ amide CSP (CSP 2) and a doubly tethered N-H amide CSP (CSP 3) under an identical aqueous mobile phase condition. CSP 4 was found to be generally better than other CSPs in terms of the separation factors (${\alpha}$) and resolutions (RS). The retention times of analytes denoted by the retention factors ($k_1$) on CSP 4 were quite long compared to those on other CSPs because of the improved lipophilicity of CSP 4. The long retention times of analytes on CSP 4 were successfully controlled by the addition of a small amount of ammonium acetate to aqueous mobile phase without hurting the chiral recognition efficiency. The variation of the content and type of organic and acidic modifier in aqueous mobile phase was found not to change the chiral recognition efficiency significantly.