Selective Nitrate Binding in Competitive Hydrogen Bonding Solvents: Do Anion-π Interactions Facilitate Nitrate Selectivity?
New tripodal urea receptors demonstrate preferential binding of anions over competitive hydrogen bonding solvents. 1H NMR titrations in 10 % [D6]DMSO/CDCl3 show a higher affinity for nitrate over the halides for the fluorinated receptor, which is lost when the fluorine atoms are absent. An anion–π i...
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| Published in | Angewandte Chemie International Edition Vol. 52; no. 39; pp. 10275 - 10280 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
WILEY-VCH Verlag
23.09.2013
WILEY‐VCH Verlag Wiley |
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| Abstract | New tripodal urea receptors demonstrate preferential binding of anions over competitive hydrogen bonding solvents. 1H NMR titrations in 10 % [D6]DMSO/CDCl3 show a higher affinity for nitrate over the halides for the fluorinated receptor, which is lost when the fluorine atoms are absent. An anion–π interaction between the nitrate and the π‐system of the ethynyl‐substituted arene is proposed as the source of this selectivity. |
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| AbstractList | New tripodal urea receptors demonstrate preferential binding of anions over competitive hydrogen bonding solvents.
1
H NMR titrations in 10% DMSO-
d
6
/CDCl
3
show a higher affinity for nitrate over the halides for the fluorinated receptor, which is lost when the fluorines are removed. An “anion–π” interaction between the nitrate and the π-system of the ethynyl-substituted arene is proposed as the source of this selectivity. New tripodal urea receptors demonstrate preferential binding of anions over competitive hydrogen bonding solvents. 1H NMR titrations in 10 % [D6]DMSO/CDCl3 show a higher affinity for nitrate over the halides for the fluorinated receptor, which is lost when the fluorine atoms are absent. An anion–π interaction between the nitrate and the π‐system of the ethynyl‐substituted arene is proposed as the source of this selectivity. New tripodal urea receptors demonstrate preferential binding of anions over competitive hydrogen bonding solvents. super(1)HNMR titrations in 10% [D sub(6)]DMSO/CDCl sub(3) show a higher affinity for nitrate over the halides for the fluorinated receptor, which is lost when the fluorine atoms are absent. An anion- pi interaction between the nitrate and the pi -system of the ethynyl-substituted arene is proposed as the source of this selectivity. |
| Author | Haley, Michael M. Johnson, Darren W. Watt, Michelle M. Zakharov, Lev N. |
| Author_xml | – sequence: 1 givenname: Michelle M. surname: Watt fullname: Watt, Michelle M. organization: Department of Chemistry and Biochemistry & Materials Science Institute, University of Oregon, Eugene, OR 97403-1253 (USA) – sequence: 2 givenname: Lev N. surname: Zakharov fullname: Zakharov, Lev N. organization: CAMCOR-Center for Advanced Materials Characterization in Oregon, University of Oregon, Eugene, OR 97403-1443 (USA) – sequence: 3 givenname: Michael M. surname: Haley fullname: Haley, Michael M. email: haley@uoregon.edu organization: Department of Chemistry and Biochemistry & Materials Science Institute, University of Oregon, Eugene, OR 97403-1253 (USA) – sequence: 4 givenname: Darren W. surname: Johnson fullname: Johnson, Darren W. email: dwj@uoregon.edu organization: Department of Chemistry and Biochemistry & Materials Science Institute, University of Oregon, Eugene, OR 97403-1253 (USA) |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/23939999$$D View this record in MEDLINE/PubMed |
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| Keywords | anion- interactions TRANSPORT DESIGN host-guest systems receptors RECOGNITION anion recognition IODINATION supramolecular chemistry anion-π interactions |
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| Notes | National Science Foundation - No. CHE-0923589; No. DGE-0742540 ark:/67375/WNG-WDT26KGR-D Oregon State University - No. P30ES000210 ArticleID:ANIE201303881 NIH - No. R01-GM087398 istex:B1A600B4B29732F16FEC0B65CEED911BD9132FAF This work was supported by NIH grant R01-GM087398, which also funded early stage intellectual property that was licensed by SupraSensor Technologies, a company co-founded by the principal investigators. We also thank the National Science Foundation for support in the form of an instrumentation grant (CHE-0923589) and a GK12 fellowship to M.M.W. (DGE-0742540). The authors acknowledge the Biomolecular Mass Spectrometry Core of the Environmental Health Sciences Core Center at Oregon State University (NIH P30ES000210). We thank Timothy E. Robitshek for assistance in the synthesis of compound 2. 2 This work was supported by NIH grant R01‐GM087398, which also funded early stage intellectual property that was licensed by SupraSensor Technologies, a company co‐founded by the principal investigators. We also thank the National Science Foundation for support in the form of an instrumentation grant (CHE‐0923589) and a GK12 fellowship to M.M.W. (DGE‐0742540). The authors acknowledge the Biomolecular Mass Spectrometry Core of the Environmental Health Sciences Core Center at Oregon State University (NIH P30ES000210). We thank Timothy E. Robitshek for assistance in the synthesis of compound . NIH RePORTER ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
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| Snippet | New tripodal urea receptors demonstrate preferential binding of anions over competitive hydrogen bonding solvents. 1H NMR titrations in 10 % [D6]DMSO/CDCl3... New tripodal urea receptors demonstrate preferential binding of anions over competitive hydrogen bonding solvents. super(1)HNMR titrations in 10% [D... New tripodal urea receptors demonstrate preferential binding of anions over competitive hydrogen bonding solvents. 1 H NMR titrations in 10% DMSO- d 6 /CDCl 3... |
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| SubjectTerms | anion recognition anion-π interactions Anions - chemistry Binding Chemistry Chemistry, Multidisciplinary Halogenation Halogens - chemistry host-guest systems Hydrogen Bonding Models, Molecular Nitrates Nitrates - chemistry Physical Sciences Receptors Science & Technology Selectivity Solvents supramolecular chemistry Titration Urea - chemistry Ureas |
| Title | Selective Nitrate Binding in Competitive Hydrogen Bonding Solvents: Do Anion-π Interactions Facilitate Nitrate Selectivity? |
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