Kim Sung-Gon, Kim Kyung-Hyun, Kim Young Kook, Shin Seung Koo, Ahn Kyo Han
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.
J Am Chem Soc. 2003 Nov 12;125(45):13819-24. doi: 10.1021/ja037031p.
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.
通过利用三中心（分叉）氢键的合理方法实现了β-手性伯铵离子的对映体识别。对各种选定客体的萃取实验表明，分叉氢键对手性识别起着关键作用。通过包合物获得的X射线数据证实了这种相互作用。利用分叉氢键，我们的C(3)对称三脚架恶唑啉受体对手性分子的识别通常扩展到α-、β-和α,β-手性胺的铵离子。简单的分子模型，通过引入分叉氢键，解释了手性识别模式。
