Synthesis and properties of novel cage-functionalized crown ethers and cryptands.

• Main Author: Hazlewood, Anna
• Other Authors: Marchand, Alan P.
• Format: Others
• Language: English
• Published: University of North Texas 2001
• Subjects: Crown ethers.; Cyclic compounds.; Host-guest interactions; Selective metal cation complexation; Crown ether synthesis
• Online Access: https://digital.library.unt.edu/ark:/67531/metadc2896/

A novel cryptand was synthesized which contained a 3,5-disubstituted-4- oxahexacyclo[5.4.1.02,6.03,10.05,9.08,11] dodecane "cage" moiety. In alkali metal picrate extraction experiments the cryptand exhibited high avidity towards Rb+ and Cs+, when compared with the corresponding model compound. A computational study of a series of cage-functionalized cryptands and their alkali metal-complexes was performed. The X-ray crystal structure of a K+-complexed bis-cage-annulated 20-crown-6 was obtained. The associated picrate anion was found to be intimately involved in stabilization of the host-guest complex. The interaction energy between the host-guest complex and picrate anion has been calculated, and the energy thereby obtained has been corrected for basis set superposition error.