(Thio)ureido anion receptors based on a 1,3-alternate oxacalix[2]arene[2]pyrimidine scaffold.

The Journal of organic chemistry

PubMedID: 22360444

Van Rossom W, Caers J, Robeyns K, Van Meervelt L, Maes W, Dehaen W. (Thio)ureido anion receptors based on a 1,3-alternate oxacalix[2]arene[2]pyrimidine scaffold. J Org Chem. 2012;77(6):2791-7.
In pursuit of highly preorganized macrocyclic host molecules for the complexation of anions, a series of oxacalix[2]arene[2]pyrimidine-based bis(thio)ureido receptors were synthesized and fully characterized. The pincer-like 1,3-alternate conformation of the oxacalix[4]arene scaffold, essential for an efficient host-guest interaction, was visualized by single-crystal X-ray analysis and supported by variable-temperature NMR studies. The anion binding properties of the receptors were evaluated via (1)H NMR titration experiments, showing intermolecular interactions with H(2)PO(4)(-), AcO(-), BzO(-), and Cl(-) ions. The host molecule bearing 4-nitrophenyl substituents on the bisurea binding pocket showed association constants in the range of 200-400 M(-1) in the strongly competitive solvent mixture of DMSO/0.5% H(2)O.