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Highly efficient chiral resolution of dl-arginine by cocrystal formation followed by recrystallization under preferential-enrichment conditions

Iwama, Sekai, Kuyama, Kazunori, Mori, Yuko, Manoj, Kochunnoonny, Gonnade, Rajesh G., Suzuki, Katsuaki, Hughes, Colan Evan, Williams, Philip Andrew, Harris, Kenneth David Maclean, Veesler, Stéphane, Takahashi, Hiroki, Tsue, Hirohito and Tamura, Rui 2014. Highly efficient chiral resolution of dl-arginine by cocrystal formation followed by recrystallization under preferential-enrichment conditions. Chemistry - a European Journal 20 (33) , pp. 10343-10350. 10.1002/chem.201402446

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Abstract

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 13C NMR spectroscopic studies on the crystallization process, a new mechanism of phase transition that can induce preferential enrichment is proposed.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: WileyBlackwell
ISSN: 0947-6539
Last Modified: 08 May 2019 02:27
URI: http://orca.cf.ac.uk/id/eprint/61890

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