Approach to the thermodynamics of enantiomer separation by gas chromatography. Enantioselectivity between the chiral inhalation anesthetics enflurane, isoflurane and desflurane and a diluted gamma-cyclodextrin derivative.
The thermodynamics of enantioselectivity, -delta D,L(delta G), -delta D,L(delta H), delta D,L(delta S) and Tiso, have been determined by gas chromatography employing the concept of the retention increment R' for the inhalation anesthetics enflurane (1), isoflurane (2) and desflurane (3) and the selector octakis(3-O-butanoyl-2,6-di-O-n-pentyl)-gamma-cyclodextrin (4) in the polysiloxane SE-54. It is shown that the separation factor alpha is concentration-dependent. Therefore, the separation factor alpha should not be employed as a criterion for enantioselectivity in diluted systems. The -delta DL(delta G) data for 1 and 4 are corroborated by 1H NMR spectroscopic measurements.
Schurig
V
V
Institut für Organische Chemie, Universität Tübingen, Germany.
Juza
M
M
D018685:Anesthetics, Inhalation / Q000737:chemistry* / Q000302:isolation & purification; D002849:Chromatography, Gas / Q000379:methods*; D003505:Cyclodextrins / Q000737:chemistry; D000077335:Desflurane; D004737:Enflurane / Q000737:chemistry* / Q000302:isolation & purification; D007530:Isoflurane / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D012680:Sensitivity and Specificity; D013237:Stereoisomerism; D013816:Thermodynamics
D018685:Anesthetics, Inhalation; D003505:Cyclodextrins; D004737:Enflurane; D000077335:Desflurane; D007530:Isoflurane