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Chirality Switching in the Crystallization of 1-(4-Chlorophenyl)ethylamine with Binaphthoic Acid by Ketimine Formation

Title
Chirality Switching in the Crystallization of 1-(4-Chlorophenyl)ethylamine with Binaphthoic Acid by Ketimine Formation
Authors
Jin, Ying-JiChoi, YunseoChen, QianShirbhate, Mukesh EknathHuang, HaofeiKim, YoungmeeKim, Sung-JinJun, Moo-JinKoo, Eon CheolKim, Kwan Mook
Ewha Authors
김성진김영미김관묵
SCOPUS Author ID
김성진scopus; 김영미scopus; 김관묵scopus
Issue Date
2016
Journal Title
BULLETIN OF THE KOREAN CHEMICAL SOCIETY
ISSN
0253-2964JCR Link1229-5949JCR Link
Citation
vol. 37, no. 10, pp. 1690 - 1695
Keywords
Chirality switchingKetimineStereoselective crystallizationBinaphthoic acid
Publisher
WILEY-V C H VERLAG GMBH
Indexed
SCI; SCIE; SCOPUS; KCI WOS scopus
Abstract
Axially chiral binaphthoic acid (BNA) was studied as a resolving agent for a stereoselective crystallization of 1-(4-chlorophenyl)ethylamine (CPEA). The diastereomeric pair of (R)-BNA/(S)-CPEA crystallizes in methylene chloride, on the other hand, the pair of (S)-BNA/(S)-CPEA crystallizes in acetone. The switch of the solubility of the diastereomeric pair is due to the imine formation with acetone. The very low solubility of the BNA/imine pair appears to be responsible for the fast and complete imine formation. The crystal structure of the BNA part in both crystals of the diastereomers maintains a same feature. Asymmetric chiral channels and pockets composed by intermolecular packing of BNA molecules appear in the crystal structures, and the robustness of them seem to contribute to the recognition of the chirality of CPEA with high selectivity.
DOI
10.1002/bkcs.10929
Appears in Collections:
자연과학대학 > 화학·나노과학전공 > Journal papers
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