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 inAngewandte Chemie International Edition Vol. 52; no. 39; pp. 10275 - 10280
Main Authors Watt, Michelle M., Zakharov, Lev N., Haley, Michael M., Johnson, Darren W.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 23.09.2013
WILEY‐VCH Verlag
Wiley
Subjects
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
anion- interactions
TRANSPORT
DESIGN
host-guest systems
receptors
RECOGNITION
anion recognition
IODINATION
supramolecular chemistry
anion-π interactions
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Summary: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.
Bibliography: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
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NIH RePORTER
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ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.201303881