Issue 7, 2015

Stereoelectronic effects: a simple yet powerful tool to manipulate anion affinity

Abstract

Different strategies are employed in designing strong and selective anion receptors but stereoelectronic effects have been largely ignored. In this work, the stereo configuration of a non-interacting ether is found to have a large impact of more than two orders of magnitude on the binding of a rigid diol with tetrabutylammonium chloride in acetonitrile-d3. A favorable carbon–oxygen dipole and an intramolecular C–H⋯OH hydrogen bond in an equatorially substituted ether is found to be energetically more important than a stabilizing hydrogen bond in the corresponding axially oriented alcohol. IR spectroscopy is also used to probe the structures of the bound complexes and several binding motifs are identified.

Graphical abstract: Stereoelectronic effects: a simple yet powerful tool to manipulate anion affinity

Supplementary files

Article information

Article type
Paper
Submitted
24 Nov 2014
Accepted
16 Dec 2014
First published
17 Dec 2014

Org. Biomol. Chem., 2015,13, 2170-2176

Stereoelectronic effects: a simple yet powerful tool to manipulate anion affinity

M. Samet, A. Fattahi and S. R. Kass, Org. Biomol. Chem., 2015, 13, 2170 DOI: 10.1039/C4OB02470B

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