Title: (Thio)ureido Anion Receptors Based on a 1,3-Alternate Oxacalix[2]arene[2]pyrimidine Scaffold
Authors: Van Rossom, Wim ×
Caers, Jef
Robeyns, Koen
Van Meervelt, Luc
Maes, Wouter
Dehaen, Wim #
Issue Date: Mar-2012
Publisher: American Chemical Society
Series Title: Journal of Organic Chemistry vol:77 issue:6 pages:2791-2797
Abstract: 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.
ISSN: 0022-3263
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Biochemistry, Molecular and Structural Biology Section
× corresponding author
# (joint) last author

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