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Cited by 293

The DOI matches its Crossref record; 45 of the 45 references it cites were found in a registry or an index.

Anion Receptors Composed of Hydrogen- and Halogen-Bond Donor Groups: Modulating Selectivity With Combinations of Distinct Noncovalent Interactions

Chudzinski, Michael G., McClary, Corey A., Taylor, Mark S.·2011·Journal of the American Chemical Society
DOI 10.1021/ja202096f
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Abstract

Studies of a series of urea-based anion receptors designed to probe the potential for anion recognition through combinations of hydrogen and halogen bonding are presented. Proton- and fluorine-NMR spectroscopy indicates that the two interactions act in concert to achieve binding of certain anions, a conclusion supported by computational studies. Replacement of the halogen-bond donating iodine substituent by fluorine (which does not participate in halogen bonding) enables estimation of the contribution of this interaction to the free energy of anion binding. Evidence for attractive contacts between anions and electron-deficient arenes arising from the use of perfluoroarene-functionalized ureas as control receptors is also discussed. The magnitude of the free energy contribution of halogen bonding depends both on the geometric features of the group linking the hydrogen- and halogen-bond donor groups and on the identity of the bound anion. The results are interpreted in relation to fundamental features of the halogen-bonding interaction, including its directionality and unusual preference for halides over oxoanions. Cooperation between two distinct noncovalent interactions leads to unusual effects on receptor selectivity, a result of fundamental differences in the interactions of halogen- and hydrogen-bond donor groups with anions.

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Metadata

Authors
Chudzinski, M. G., McClary, C. A., & Taylor, M. S.
Venue
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Published
2011-06-13
Volume
133
Issue
27
Pages
10559-10567
ISSN
  • 0002-7863 (ISSN-L)
  • 1520-5126
DOI
10.1021/ja202096f
OpenAlex
W2328419081
Cited by
293
References
45
FWCI
27.06
Type
journal article
Language
en
Open access
closed

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