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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 | Source: | 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. | Document URI: | http://hdl.handle.net/1942/13300 | ISSN: | 0022-3263 | e-ISSN: | 1520-6904 | DOI: | 10.1021/jo300004p | ISI #: | 000301516100020 | Category: | A1 | Type: | Journal Contribution | Validations: | ecoom 2013 |
Appears in Collections: | Research publications |
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Van Rossom et al, JOC 2012, just accepted.pdf Restricted Access | 579.33 kB | Adobe PDF | View/Open Request a copy |
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