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Quantification of the H-Bond-Donating Ability of Trifluoromethyl Ketone Hydrates Using a Colorimetric Sensor

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    Quantification of the H-Bond-Donating Ability of Trifluoromethyl Ketone Hydrates Using a Colorimetric Sensor
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2025, 90, 21, 7120–7124
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    https://doi.org/10.1021/acs.joc.4c03046
    Published May 15, 2025
    Copyright © 2025 American Chemical Society
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    Abstract

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    Trifluoromethyl ketones (TFMKs) readily form stable hydrates and hemiketals in solution, allowing them to interact with biomolecules as hydrogen-bond donors. This interaction is governed by both the hydration equilibrium and the intrinsic hydrogen-bonding strength for a given compound. The hydrogen-bond-donating abilities for aryl, heterocyclic, and alkyl TFMKs were experimentally determined by using UV–vis titrations with a colorimetric sensor. Values were also adjusted based on the percent hydrate present in solution to provide insight into the hydrogen-bond-donating ability of the hydrate species.

    Copyright © 2025 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.joc.4c03046.

    • Experimental procedures and titration data (PDF)

    • UV–vis absorption data (ZIP)

    • FAIR data, including the primary NMR FID files, for compounds 1–14 (ZIP)

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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2025, 90, 21, 7120–7124
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.joc.4c03046
    Published May 15, 2025
    Copyright © 2025 American Chemical Society
    Request reuse permissions

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