Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 6, Pages 2791-2797Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo300004p
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Funding
- FWO (Fund for Scientific Research - Flanders)
- KU Leuven
- Ministerie voor Wetenschapsbeleid
- Grants-in-Aid for Scientific Research [11F01760] Funding Source: KAKEN
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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 H-1 NMR titration experiments, showing intermolecular interactions with H2PO4-, 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% H2O.
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