期刊
JOURNAL OF FLUORINE CHEMISTRY
卷 131, 期 4, 页码 517-520出版社
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jfluchem.2009.12.007
关键词
Self-disproportionation of enantiomers; Distillation; Trifluorolactate; Infinite hydrogen bonding network; X-ray diffraction analysis; Electrostatic repulsion; Negative charge on trifluoromethyl group
资金
- Okayama Foundation for Science and Technology
- Wesco Scientific Promotion Foundation
- ENEOS Hydrogen Trust
The paper provides evidence for the existence of a multi-center hydrogen bonding network of trifluorolactate, the structure of which was elucidated by single crystal X-ray diffraction analysis, in the liquid state. We reported that the trifluorolactate experienced discrimination of its enantiomeric excess by distillation. X-ray crystallographic analyses of the single crystals of the trifluorolactates suggested that the phenomenon could be caused by a homo-chiral recognizing hydrogen bonding system. Low-angle X-ray diffraction measurement of the trifluorolactate in the liquid state showed a ca. 5 angstrom repeated, which indicates the existence of the hydrogen bonding network in the liquid state. Here, the chiral recognition could be caused by the electrostatic repulsion of the negative charges on trifluoromethyl groups. (C) 2010 Elsevier B.V. All rights reserved.
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