Study of the mechanism of enantioseparation part VI: thermodynamic study of HPLC separation of some enantiomers of phenylcarbamic acid derivatives on a (S,S) Whelk-O 1 column |
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Authors: | Dungelová Jana Lehotay Jozef Krupcík Jan Cizmárik Jozef Armstrong Daniel W |
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Affiliation: | Department of Analytical Chemistry, Faculty of Chemical and Food Technology, Slovak University of Technology, Bratislava, Slovakia. |
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Abstract: | The enantiomers of thirteen 2-, 3-, and 4-alkoxyphenylcarbamic acid 2-methoxy-1-[(4-methylpiperazino)methyl]ethyl ester were separated on a (S,S) Whelk-O 1 CSP column isothermally in the range of 0-50 degrees C at 10 degrees C increments, using methanol/ water (90/10, v/v) containing 17.5 mmol L(-1) acetic acid and 14.36 mmol L(-1) triethylamine as a mobile phase. The dependence of the natural logarithms of retention and selectivity factors (In k, In alpha, respectively) on the inverse of temperature, 1/T, was used to determine thermodynamic data of enantiomers of alkoxysubstituted phenylcarbamic acid 2-methoxy-1-[(4-methylpiperazino) methyl]ethyl esters. Enthalpyentropy compensation plots showed that all of the compounds in this study separate via the same enthalpy-driven chiral recognition mechanism. |
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Keywords: | Enantiomer separation HPLC (S,S)‐Whelk‐O 1 CSP 2‐, 3‐, and 4‐alkoxyphenylcarbamic acid 2‐methoxy‐1‐[(4‐methylpiperazino)methyl]ethyl ester Thermodynamic study Retention behavior Enthalpy‐entropy compensation |
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