title: Combinatorial approach to enantiomeric discrimination: synthesis and (19)F NMR screening of a chiral ionic liquid-modified silane library.
abstract: A parallel library of chiral ionic liquid (CIL)-modified silanes as potential chiral selectors was synthesized, and their enantiomeric discrimination abilities were screened by use of (19)F NMR spectroscopy. The screening method allows for rapid identification of the most enantioselective members of the library and simultaneous investigation of their chiral recognition mechanisms. The library compounds were synthesized using quaternization and anion-exchange reactions. Three major parameters (type of chiral cations, anions, and linker chain lengths) were included and investigated during the synthesis and screening. As expected, the structure of the chiral cation was found to play an important role in determining chiral recognition abilities. In addition, several types of intermolecular interactions including ion-pair, hydrogen bonding, pi-pi stacking, dipole stacking, and steric interactions were found to impact chiral discrimination.
authors.affiliation: Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803, USA.
authors.forename: Min
authors.initials: M
authors.lastname: Li
authors.forename: Jerry
authors.initials: J
authors.lastname: Gardella
authors.forename: David K
authors.initials: DK
authors.lastname: Bwambok
authors.forename: Bilal
authors.initials: B
authors.lastname: El-Zahab
authors.forename: Sergio
authors.initials: S
authors.lastname: de Rooy
authors.forename: Marsha
authors.initials: M
authors.lastname: Cole
authors.forename: Mark
authors.initials: M
authors.lastname: Lowry
authors.forename: Isiah M
authors.initials: IM
authors.lastname: Warner
mesh_terms: D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D005462:Fluorine Radioisotopes; D006860:Hydrogen Bonding; D052578:Ionic Liquids / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012821:Silanes / Q000138:chemical synthesis* / Q000737:chemistry; D054852:Small Molecule Libraries; D013237:Stereoisomerism
chemical_list: D005462:Fluorine Radioisotopes; D052578:Ionic Liquids; D012821:Silanes; D054852:Small Molecule Libraries