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

Samet, M ; Sharif University of Technology | 2015

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  1. Type of Document: Article
  2. DOI: 10.1039/c4ob02470b
  3. Publisher: Royal Society of Chemistry , 2015
  4. Abstract:
  5. 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
  6. Keywords:
  7. Chlorine compounds ; Anion receptor ; Binding motif ; Orders of magnitude ; Stereoelectronic effect ; Tetrabutyl-ammonium chloride ; Acetonitrile derivative ; Ether derivative ; Quaternary ammonium derivative ; Tetrabutylammonium ; Chemical structure ; Chemistry ; Hydrogen bond ; Stereoisomerism ; Acetonitriles ; Anions ; Ethers ; Hydrogen Bonding ; Molecular Structure ; Quaternary Ammonium Compounds
  8. Source: Organic and Biomolecular Chemistry ; Volume 13, Issue 7 , Dec , 2015 , Pages 2170-2176 ; 14770520 (ISSN)
  9. URL: http://pubs.rsc.org/en/Content/ArticleLanding/2015/OB/C4OB02470B#!divAbstract