Strong enantioselective self-recognition of a small chiral molecule.
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.
Snyder
Seth E
SE
Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, USA.
Volkers
Phillip I
PI
Engebretson
David A
DA
Lee
Wonjae
W
Pirkle
William H
WH
Carey
James R
JR
D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D007930:Leucine / Q000031:analogs & derivatives* / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
D007930:Leucine