Since their first synthesis in 1967, crown ethers have been the subject of intensive investigation in a number of fields.  Few of these investigations, however, have concerned the issue of their stereochemistry, a result of the difficulty in either preparing individual stereoisomers or isolating single isomers from the complex mixtures that often result from crown ether synthesis.  In this presentation, we detail our recent efforts to separate and identify the major stereoisomers of di-tert-butylcyclohexano-18-crown-6, a compound used in both the SREX Process for nuclear waste treatment and Sr Resin, a commercial chromatographic sorbent employed for the separation and preconcentration of radiostrontium from environmental and biological samples.  In particular, the use of isothermal titration calorimetry (ITC) in combination with ligand strain energy calculations as an approach to the identification of the separated isomers is described.

Separation and characterization of crown ether stereoisomers

245th National Meeting (2013)

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