Evidence for halogen bond covalency in acyclic and interlocked halogen-bonding receptor anion recognition
Abstract
The synthesis and anion binding properties of novel halogen-bonding (XB) bis-iodotriazole-pyridinium-containing acyclic and [2]catenane anion host systems are described. The XB acyclic receptor displays selectivity for acetate over halides with enhanced anion recognition properties compared to the analogous hydrogen-bonding (HB) acyclic receptor. A reversal in halide selectivity is observed in the XB [2]catenane, in comparison to the acyclic XB receptor, due to the interlocked host’s unique three-dimensional binding cavity, and no binding is observed for oxoanions. Notable halide anion association constant values determined for the [2]catenane in competitive organic–aqueous solvent mixtures demonstrate considerable enhancement of anion recognition as compared to the HB catenane analogue. X-ray crystallographic analysis of a series of halide catenane complexes reveal strong XB interactions in the solid state. These interactions were studied using Cl and Br K-edge X-ray Absorption Spectroscopy (XAS) indicating intense pre-edge features characteristic of charge transfer from the halide to its bonding partner (σAX←X–* ← X1s), and providing a direct measure of the degree of covalency in the halogen bond(s). Lastly, the data reveal that the degree of covalency is similar to that which is observed in transition metal coordinate covalent bonds. These results are supported by DFT results, which correlate well withmore »
- Authors:
-
- Univ. of Oxford, Oxford (United Kingdom)
- Univ. of British Columbia, Vancouver, BC (Canada)
- Univ. of Oxford, Oxford (United Kingdom); Univ. of British Columbia, Vancouver, BC (Canada)
- Publication Date:
- Research Org.:
- Univ. of British Columbia, Vancouver, BC (Canada); Univ. of Oxford, Oxford (United Kingdom)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES); USDOE Office of Science (SC), Biological and Environmental Research (BER)
- OSTI Identifier:
- 1345823
- Grant/Contract Number:
- AC02-76SF00515
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Journal of the American Chemical Society
- Additional Journal Information:
- Journal Volume: 137; Journal Issue: 1; Journal ID: ISSN 0002-7863
- Publisher:
- American Chemical Society (ACS)
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Citation Formats
Robinson, Sean W., Mustoe, Chantal L., White, Nicholas G., Brown, Asha, Thompson, Amber L., Kennepohl, Pierre, and Beer, Paul D. Evidence for halogen bond covalency in acyclic and interlocked halogen-bonding receptor anion recognition. United States: N. p., 2014.
Web. doi:10.1021/ja511648d.
Robinson, Sean W., Mustoe, Chantal L., White, Nicholas G., Brown, Asha, Thompson, Amber L., Kennepohl, Pierre, & Beer, Paul D. Evidence for halogen bond covalency in acyclic and interlocked halogen-bonding receptor anion recognition. United States. https://doi.org/10.1021/ja511648d
Robinson, Sean W., Mustoe, Chantal L., White, Nicholas G., Brown, Asha, Thompson, Amber L., Kennepohl, Pierre, and Beer, Paul D. Fri .
"Evidence for halogen bond covalency in acyclic and interlocked halogen-bonding receptor anion recognition". United States. https://doi.org/10.1021/ja511648d. https://www.osti.gov/servlets/purl/1345823.
@article{osti_1345823,
title = {Evidence for halogen bond covalency in acyclic and interlocked halogen-bonding receptor anion recognition},
author = {Robinson, Sean W. and Mustoe, Chantal L. and White, Nicholas G. and Brown, Asha and Thompson, Amber L. and Kennepohl, Pierre and Beer, Paul D.},
abstractNote = {The synthesis and anion binding properties of novel halogen-bonding (XB) bis-iodotriazole-pyridinium-containing acyclic and [2]catenane anion host systems are described. The XB acyclic receptor displays selectivity for acetate over halides with enhanced anion recognition properties compared to the analogous hydrogen-bonding (HB) acyclic receptor. A reversal in halide selectivity is observed in the XB [2]catenane, in comparison to the acyclic XB receptor, due to the interlocked host’s unique three-dimensional binding cavity, and no binding is observed for oxoanions. Notable halide anion association constant values determined for the [2]catenane in competitive organic–aqueous solvent mixtures demonstrate considerable enhancement of anion recognition as compared to the HB catenane analogue. X-ray crystallographic analysis of a series of halide catenane complexes reveal strong XB interactions in the solid state. These interactions were studied using Cl and Br K-edge X-ray Absorption Spectroscopy (XAS) indicating intense pre-edge features characteristic of charge transfer from the halide to its bonding partner (σAX←X–* ← X1s), and providing a direct measure of the degree of covalency in the halogen bond(s). Lastly, the data reveal that the degree of covalency is similar to that which is observed in transition metal coordinate covalent bonds. These results are supported by DFT results, which correlate well with the experimental data.},
doi = {10.1021/ja511648d},
journal = {Journal of the American Chemical Society},
number = 1,
volume = 137,
place = {United States},
year = {Fri Dec 05 00:00:00 EST 2014},
month = {Fri Dec 05 00:00:00 EST 2014}
}
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