Crucial role of three-center hydrogen bonding in a challenging chiral molecular recognition |
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Authors: | Kim Sung-Gon Kim Kyung-Hyun Kim Young Kook Shin Seung Koo Ahn Kyo Han |
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Institution: | Department of Chemistry and Center for Integrated Molecular Systems, Division of Molecular and Life Science, Pohang University of Science and Technology, San 31 Hyoja-dong, Pohang 790-784, South Korea. |
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Abstract: | The enantio-discrimination of beta-chiral primary ammonium ions is achieved by a rational approach that utilizes three-center (bifurcated) hydrogen bonding. The extraction experiments on various selected guests reveal that the bifurcated H-bonding plays a crucial role for the chiral discrimination. The X-ray data obtained for an inclusion complex substantiate such interactions. Using the bifurcated H-bonding, the chiral molecular recognition with our C(3)-symmetric tripodal oxazoline receptors is extended generally toward ammonium ions of alpha-, beta-, and alpha,beta-chiral amines. Simple molecular models, evoking the bifurcated H-bonding, explain the chiral discrimination modes. |
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