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Highly Efficient Chiral Resolution of dl ‐Arginine by Cocrystal Formation Followed by Recrystallization under Preferential‐Enrichment Conditions
Author(s) -
Iwama Sekai,
Kuyama Kazunori,
Mori Yuko,
Manoj Kochunnoonny,
Gonnade Rajesh G.,
Suzuki Katsuaki,
Hughes Colan E.,
Williams P. Andrew,
Harris Kenneth D. M.,
Veesler Stéphane,
Takahashi Hiroki,
Tsue Hirohito,
Tamura Rui
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201402446
Subject(s) - crystallization , cocrystal , recrystallization (geology) , eutectic system , chemistry , fumaric acid , chiral resolution , crystallography , enantiomer , chemical engineering , stereochemistry , organic chemistry , molecule , microstructure , paleontology , hydrogen bond , engineering , biology
An excellent chiral symmetry‐breaking spontaneous enantiomeric resolution phenomenon, denoted preferential enrichment, was observed on recrystallization of the 1:1 cocrystal of dl ‐arginine and fumaric acid, which is classified as a racemic compound crystal with a high eutectic ee value (>95 %), under non‐equilibrium crystallization conditions. On the basis of temperature‐controlled video microscopy and in situ time‐resolved solid‐state 13 C NMR spectroscopic studies on the crystallization process, a new mechanism of phase transition that can induce preferential enrichment is proposed.