Abstract
A new family of p- tert-butylcalix[4]arenes functionalized at the lower rim with α-ketoamide or α-hydroxyamide functions has been prepared. The 1H and 13C NMR spectra indicate that the macrocycles preferably adopt a cone conformation. X-ray crystal study of the α-ketoamide derivative 4a shows the flattened cone conformation in the solid state. Reduction of α-ketoamide 4ab has produced the α-hydroxyamide derivatives 6ab . The introduction of chiral moieties on the lower rim position of the calix[4]arene allowed the synthesis of the chiral derivatives 7 and 8 . Host–guest complexation properties towards various anions of the chiral α-hydroxyamide 8 have been examined by 1H NMR spectroscopy. This new receptor has shown promising selectivity for H 2 PO 4 - and N-tosyl-( L)-alaninate.
Published Version
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