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    Revision of the Gas-Phase Acidity Scale below 300 kcal mol−1
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    Institute of Chemistry, University of Tartu, 2 Jakobi Street, 51014 Tartu, Estonia, Institute for Materials Chemistry and Engineering, Kyushu University, Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan, and Institute of Organic Chemistry, Ukrainian National Academy of Sciences, 5 Murmanskaya Street, Kiev 02094, Ukraine
    * To whom correspondence should be addressed. E-mail: [email protected] (I.A.K.) and [email protected] (I.L.). Phone: +372 5 184 176. Fax: +372 7 375 264.
    †University of Tartu.
    ‡Kyushu University.
    §Ukrainian National Academy of Sciences.
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    The Journal of Physical Chemistry A

    Cite this: J. Phys. Chem. A 2009, 113, 29, 8421–8424
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    https://doi.org/10.1021/jp903780k
    Published July 1, 2009
    Copyright © 2009 American Chemical Society
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    Abstract

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    The gas-phase acidity (GA) scale from (CF3CO)2NH to (C2F5SO2)2NH—about a 24 kcal mol−1 range of gas-phase acidities—was reexamined using the Fourier transform ion cyclotron resonance equilibrium measurement approach. Some additions and modifications to the standard methodology of GA measurements were introduced (estimation of partial pressures from mass spectra of the compounds, instead of the pressure gauge readings and use of long reaction times) to achieve higher reliability. Gas-phase acidities of 18 compounds were determined for the first time. The results reveal a contraction of the previously published values in this part of the scale. In particular, the GA values of (CF3SO2)2NH and (C2F5SO2)2NH (important components of lithium ion battery electrolytes and ionic liquids) were revised toward stronger acidities from 291.8 kcal mol−1 to 286.5 kcal mol−1 and from 289.4 kcal mol−1 to 283.7 kcal mol−1 (i.e., by 5.3 and 5.7 kcal mol−1), respectively. Experimental and computational evidence is presented in support of the current results.

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    Details of the measurement and calculation methods. The origin of the compounds. Computational Cartesian coordinates of the acids and anions. This material is available free of charge via the Internet at http://pubs.acs.org.

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    The Journal of Physical Chemistry A

    Cite this: J. Phys. Chem. A 2009, 113, 29, 8421–8424
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jp903780k
    Published July 1, 2009
    Copyright © 2009 American Chemical Society
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