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Please use this identifier to cite or link to this item: http://hdl.handle.net/1942/13300

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: 2012
Citation: JOURNAL OF ORGANIC CHEMISTRY, 77 (6), p. 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 was 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 1H NMR titration experiments, showing intermolecular interactions with H2PO4–, AcO–, B zO– 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 thestrongly competitive solvent mixture DMSO/0.5% H2O.
URI: http://hdl.handle.net/1942/13300
DOI: 10.1021/jo300004p
ISI #: 000301516100020
ISSN: 0022-3263
Category: A1
Type: Journal Contribution
Validation: ecoom, 2013
Appears in Collections: Research publications

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