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.
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.
Dungelová
Jana
J
Department of Analytical Chemistry, Faculty of Chemical and Food Technology, Slovak University of Technology, Bratislava, Slovakia.
Lehotay
Jozef
J
Krupcík
Jan
J
Cizmárik
Jozef
J
Armstrong
Daniel W
DW
D019342:Acetic Acid / Q000737:chemistry; D002219:Carbamates / Q000737:chemistry; D002244:Carbon / Q000032:analysis / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D019277:Entropy; D006358:Hot Temperature; D008956:Models, Chemical; D013237:Stereoisomerism; D013696:Temperature; D013816:Thermodynamics; D013997:Time Factors
D002219:Carbamates; D002244:Carbon; C059692:phenylcarbamic acid; D019342:Acetic Acid