The influence of mobile phase demixion on thin-layer chromatographic enantioseparation of ibuprofen and naproxen.
In our earlier article we presented the results of tracing the enantioseparation of the two test analytes (ibuprofen and naproxen) by means of video densitometry and scanning densitometry. In that way we demonstrated an excellent performance of this combined approach to the thin-layer chromatographic detection in the area of enantioseparation. In this paper we study an impact of the four different mobile phases on the enantioseparation of the scalemic mixtures of ibuprofen and naproxen on the silica gel layers impregnated with L-arginine as chiral selector. The main component of all the investigated mobile phases is 2-propanol. Mobile phase 1 consists of pure 2-propanol, while mobile phases 2-4 contain, respectively, ca. 0.66, 1.32, and 1.98 g/L of glacial acetic acid in 2-propanol. Acetic acid is used to protonate L-arginine, as the involved retention mechanism consists of the ion pair formation between L-arginine in the cationic form and the chiral 2-arylpropionic acids (2-APAs), ibuprofen and naproxen, in the anionic form. It is shown that in the absence of glacial acetic acid no enantioseparation can be obtained. Then with adding of 0.66 g/L glacial acetic acid partial enantioseparation of the naproxen and ibuprofen antimers is obtained, with a simultaneous effect of the mobile phase demixion. With the amount of acetic acid increasing, the effect of demixion becomes increasingly perceptible. In that case the displacement effect is observed (and mathematically modeled), which results in compressing of the antimer pairs by the second front of mobile phase. The obtained results allow a deeper insight into the mechanism of enantioseparation with the two test 2-APAs. A combined impact of the crystalline chirality of silica gel and the molecular chirality of L-arginine on the vertical and the horizontal enantioseparation of ibuprofen and naproxen is also discussed.
Sajewicz
Mieczysław
M
Institute of Chemistry, Silesian University, 9 Szkolna Street, 40-006 Katowice, Poland.
Kaczmarski
Krzysztof
K
Gontarska
Monika
M
Kiszka
Sylwia
S
Kowalska
Teresa
T
D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000302:isolation & purification*; D002855:Chromatography, Thin Layer / Q000379:methods*; D002942:Circular Dichroism; D007052:Ibuprofen / Q000302:isolation & purification*; D009288:Naproxen / Q000302:isolation & purification*; D013237:Stereoisomerism
D000894:Anti-Inflammatory Agents, Non-Steroidal; D009288:Naproxen; D007052:Ibuprofen