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Issue 94, 2018
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Conformationally flexible arylethynyl bis-urea receptors bind disparate oxoanions with similar, high affinities

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Abstract

Conformationally flexible hosts with relatively small binding pockets are seldom shown to bind oxoanions preferentially over other guests. Herein, we disclose the binding of diprotic, monoprotic, and aprotic tetrahedral oxoanions with three different pyridylethynyl bis-urea scaffolds. In less polar solvent, the trend in association constants appears to be heavily influenced by solvation and entropic effects. However, in a more polar solvent, the trend in association constants matches that of the pKa of the conjugate acid of the anionic guest, as expected for H-bond donating hosts.

Graphical abstract: Conformationally flexible arylethynyl bis-urea receptors bind disparate oxoanions with similar, high affinities

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Supplementary files

Article information


Submitted
07 Sep 2018
Accepted
26 Sep 2018
First published
28 Sep 2018

Chem. Commun., 2018,54, 13208-13211
Article type
Communication
Author version available

Conformationally flexible arylethynyl bis-urea receptors bind disparate oxoanions with similar, high affinities

L. M. Eytel, A. C. Brueckner, J. A. Lohrman, M. M. Haley, P. H.-Y. Cheong and D. W. Johnson, Chem. Commun., 2018, 54, 13208
DOI: 10.1039/C8CC07301E

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