Enantiorecognition mechanisms for derivatzed cellulose under reversed phase conditions

摘要

The chiral recognition mechanism for a derivatized polysac- charide chiral stationary phase (CSP) under reversed phase con- ditions was investigated (Chiralcel OJ-R). While enantiorecogni- ti on mechanisms have been proposed for these types of phases under normal phase conditions, it is unlikely that they would apply to reversed phase conditions due to the high polarity of the eluent. lndandiol was utilized as the main probe. The effect of organic modifier, eluent anion, and temperature on enantioselec- tivity for indandiol was determined. Additionally, a number of structurally related probe~ were also investigated to define the role of various functional groups on enantioselectivity. The investigation revealed that hydrogen bonding did not have a gross direct effect on enantiorecognition but may contribute through it's effect on the tertiary structure of the CSP. It appears that inclusion is the major contributor to enantioselectivity with the size and shape of the probe being the determinant as to the extent of enantioselectivity rather than electrostatic interactions invol.ving the functional groups of the solute.