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

Masoud Samet, Alireza Fattahi, Steven R. Kass

Research output: Contribution to journalArticlepeer-review

5 Scopus citations


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.

Original languageEnglish (US)
Pages (from-to)2170-2176
Number of pages7
JournalOrganic and Biomolecular Chemistry
Issue number7
StatePublished - Feb 21 2015

Bibliographical note

Publisher Copyright:
© The Royal Society of Chemistry 2015.


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