Thermodynamic studies of complexation and enantiorecognition processes of monoterpenoids by alpha- and beta-cyclodextrin in gas chromatography.
Gas-liquid chromatography was applied in thermodynamic investigations of processes of complexation and enantioseparation by alpha- and [-cyclodextrins of chiral monoterpenoids. The distribution constants, stability constants and thermodynamic parameters enthalpy, entropy and free energy of the complexation processes were determined. It has been found that enantioseparation of monoterpenes by alpha- and beta-cyclodextrins is the result of formation of 1:2 stoichiometric complexes. When 1:1 stoichiometric complexes are formed, enantioselectivity is not observed. All investigated processes of complexation are enthalpy-driven regardless of the stoichiometry of the formed complexes. -deltaH, -TdeltaS and -deltaG of complexation process have higher values for bicyclic than for monocyclic monoterpenoids as well as for alpha-CD than for beta-CD. The first or second step of complexation may be responsible for enantioselectivity.
Skórka
Malgorzata
M
Institute of Physical Chemistry of the Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.
Asztemborska
Monika
M
Zukowski
Janusz
J
D002849:Chromatography, Gas / Q000379:methods*; D004355:Drug Stability; D013237:Stereoisomerism; D013729:Terpenes / Q000032:analysis / Q000737:chemistry* / Q000302:isolation & purification; D013816:Thermodynamics; D047391:alpha-Cyclodextrins / Q000737:chemistry*; D047392:beta-Cyclodextrins / Q000737:chemistry*
D013729:Terpenes; D047391:alpha-Cyclodextrins; D047392:beta-Cyclodextrins; C031215:betadex; C032613:alpha-cyclodextrin