Fourier transform infrared spectroscopic characterization of complexes of carbamoylated quinidine chiral selector and N-derivatized leucine enantiomers in solution - Evidence for stereoselective intermolecular interactions

Fourier transform infrared (FT-IR) spectra of 1 : 1 complexes of O-allylcar bamoyl-10,11-dihydroquinidine with (S) and (R) enantiomers of N-3,5-dinitro benzoyl (DNB) and N-2,4-dinitrophenyl (DNP) protected leucine (Leu) and N-m ethyl leucine (N-Me-Leu), respectively, as well as of the pure binding part ners are reported. For the study of the various intermolecular interaction effects, IR spectra were monitored in acetonitrile and acetonitrile/water s olutions using attenuated total reflectance with a cylindrical internal ref lection cell. The results of the FT-IR measurements are correlated with fin dings of liquid chromatographic studies in which O-allylcarbamoyl-10,11-dih ydroquinidine is used as a chiral selector immobilized onto silica for the direct chromatographic enantioseparation of N-derivatized amino acids. (C) 1999 Elsevier Science B.V. All rights reserved.