Thiacalix[4]arene spirodienone was rearranged into the corresponding phenoxathiin-based macrocycle. Alkylation of this inherently chiral system to achieve its immobilization led to a mixture of only two (out of four theoretically possible) stereoisomers. As standard NOE and dynamic NMR experiments did not lead to unambiguous determination of the structures we applied the Residual Dipolar Coupling constant (RDC) method. Poly-γ-ethyl-l-glutamate (PELG) and poly-γ-benzyl-l-glutamate (PBLG) were found to be easily applicable lyotropic liquid crystalline alignment media for the conformational analysis of thiacalixarene derivatives. Using these media the 1,2-alternate and the partial cone conformations were determined unequivocally.

Laboratory of NMR Spectroscopy University of Chemistry and Technology Prague Technická 5 166 28 Prague 6 Czech Republic

References provided by Crossref.org

Enantiodiscrimination of Inherently Chiral Thiacalixarenes by Residual Dipolar Couplings

Reactivity of phenoxathiin-based thiacalixarenes towards C-nucleophiles

The Unexpected Chemistry of Thiacalix[4]arene Monosulfoxide