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Detection and Differentiation of Neutral Organic Compounds by 19F NMR with a Tungsten Calix[4]arene Imido Complex

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    Detection and Differentiation of Neutral Organic Compounds by 19F NMR with a Tungsten Calix[4]arene Imido Complex
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    Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2013, 135, 50, 18770–18773
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    https://doi.org/10.1021/ja4106804
    Published December 3, 2013
    Copyright © 2013 American Chemical Society
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    Abstract

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    Fluorinated tungsten calix[4]arene imido complexes were synthesized and used as receptors to detect and differentiate neutral organic compounds. It was found that the binding of specific neutral organic molecules to the tungsten centers induces an upfield shift of the fluorine atom appended on the arylimido group, the extent of which is highly dependent on electronic and steric properties. We demonstrate that the specific bonding and size-selectivity of calix[4]arene tungsten–imido complex combined with 19F NMR spectroscopy is a powerful new method for the analysis of complex mixtures.

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    42. Adam J. Plaunt, Kasey J. Clear, Bradley D. Smith. 19 F NMR indicator displacement assay using a synthetic receptor with appended paramagnetic relaxation agent. Chem. Commun. 2014, 50 (72) , 10499-10501. https://doi.org/10.1039/C4CC04159C
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2013, 135, 50, 18770–18773
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ja4106804
    Published December 3, 2013
    Copyright © 2013 American Chemical Society
    Request reuse permissions

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