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

The Journal of Organic Chemistry
Wim Van RossomWim Dehaen

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 (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.

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Citations

Sep 11, 2012·The Journal of Organic Chemistry·Mahendra P SonawaneWim Van Rossom
Dec 8, 2015·Chemistry : a European Journal·Joice ThomasWim Dehaen
Nov 29, 2012·Chemical Society Reviews·Massimo Cametti, Kari Rissanen
May 27, 2016·Chemistry : a European Journal·Mandeep SinghOfer Reany
Apr 1, 2018·Chemistry : a European Journal·Ondřej JurčekAnthony P Davis
Jun 20, 2014·Organic & Biomolecular Chemistry·Wim Van RossomJonathan P Hill
May 31, 2014·Organic & Biomolecular Chemistry·Hirotsugu TomiyasuTakehiko Yamato
Jul 5, 2012·Organic & Biomolecular Chemistry·Joice ThomasWim Dehaen
Nov 15, 2017·Organic & Biomolecular Chemistry·Suguru ItoMasatoshi Asami
Dec 29, 2020·Beilstein Journal of Organic Chemistry·Tereza HoráčkováPavel Lhoták
May 17, 2014·Organic Letters·Jay Wm WackerlyJeffrey L Katz
May 23, 2015·Chemical Reviews·Nathalie BusschaertPhilip A Gale

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