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

J Org Chem. 2011 Feb 18;76(4):1159-62. doi: 10.1021/jo102148p. Epub 2011 Jan 18.

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 co-crystallization with both X-ray diffraction and chiral HPLC was particularly powerful in overcoming these difficulties for a series of chiral 3-arylbutanoic acids. Co-crystallization 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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Butyrates / chemistry*
  • Chromatography, High Pressure Liquid
  • Crystallography, X-Ray
  • Hydrogen Bonding
  • Models, Molecular
  • Salts / chemistry*
  • Solutions / chemistry
  • Stereoisomerism
  • X-Ray Diffraction

Substances

  • Butyrates
  • Salts
  • Solutions