The use of co-crystals for the determination of absolute stereochemistry: an alternative to salt formation

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The use of co-crystals for the determination of absolute stereochemistry: an alternative to salt formation

Eccles, Kevin S.; Deasy, Rebecca E.; Fábián, László; Maguire, Anita R.; Lawrence, Simon E.
Date: 2011-01
Copyright: © 2011, American Chemical Society. This document is the Accepted Manuscript version of a Published Work that appeared in final form in Crystal Growth & Design, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://pubs.acs.org/doi/abs/10.1021/jo102148p
Related: http://pubs.acs.org/doi/abs/10.1021/jo102148p
Citation: Eccles, Kevin S., Deasy,Rebecca E., Fabian, Laszlo, Maguire, Anita R., Lawrence, Simon E. (2011) 'The Use of Co-crystals for the Determination of Absolute Stereochemistry: An Alternative to Salt Formation'. Journal of Organic Chemistry, 76 (4):1159-1162. http://pubs.acs.org/doi/abs/10.1021/jo102148p
Published Version: 10.1021/jo102148p

Abstract:

Absolute stereochemistry of oils and viscous liquids can be difficult to determine. Co-crystallization involves generating a crystalline material consisting of more than one neutral compound. The combination of cocrystallization with both X-ray diffraction and chiral HPLC was particularly powerful in overcoming these difficulties for a series of chiral 3-arylbutanoic acids. Cocrystallization offers advantages over salt formation because co-crystals dissociate in solution, meaning identical HPLC conditions can be used for both the materials of interest and their co-crystals.

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