title: Strong enantioselective self-recognition of a small chiral molecule.
abstract: In the present report, we have crystallized a single enantiomer and the racemate of N-3,5-dinitrobenzoyl (DNB) leucine. In both cases, the X-ray structures show clear evidence of homochiral dimerization in the solid state. Moreover, only homochiral dimers were observed in the unit cell of the racemate, a result of solid-state enantioselective complexation. The crystal structures support a chiral recognition mechanism involving two hydrogen bonds and an offset pi-pi interaction between the DNB rings.
authors.affiliation: Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, USA.
authors.forename: Seth E
authors.initials: SE
authors.lastname: Snyder
authors.forename: Phillip I
authors.initials: PI
authors.lastname: Volkers
authors.forename: David A
authors.initials: DA
authors.lastname: Engebretson
authors.forename: Wonjae
authors.initials: W
authors.lastname: Lee
authors.forename: William H
authors.initials: WH
authors.lastname: Pirkle
authors.forename: James R
authors.initials: JR
authors.lastname: Carey
mesh_terms: D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D007930:Leucine / Q000031:analogs & derivatives* / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D007930:Leucine