Strong enantioselective self-recognition of a small chiral molecule |
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Authors: | Snyder Seth E Volkers Phillip I Engebretson David A Lee Wonjae Pirkle William H Carey James R |
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Institution: | Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, USA. |
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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. |
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