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Protonation of electroneutral p-tert-butylcalix[4]arenetetraacetic acid

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Abstract

Using 1H NMR spectroscopy together with density functional theoretical calculations, it is shown that electroneutral p-tert-butylcalix[4]arenetetraacetic acid forms an equimolar complex with a proton in the form of the H3O+ ion in nitrobenzene-d 5. Protons were offered by hydrogen bis(1,2-dicarbollyl)cobaltate and converted to hydroxonium ions by traces of water. In the resulting complex, the H3O+ cation is bound by strong hydrogen bonds to two phenoxy oxygen atoms of the parent calix[4]arene ligand and to one carbonyl oxygen of the corresponding COOH group of this ligand.

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Acknowledgments

This work was supported by the Academy of Sciences of the Czech Republic, project T 400500402, and by the Czech Ministry of Education, Youth, and Sports, projects MSM 4977751303, MSM 6046137301, and MSM 6046137307.

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Authors and Affiliations

  1. Institute of Macromolecular Chemistry, Academy of Sciences of the Czech Republic, Prague, Czech Republic

    Jaroslav Kříž & Jiří Dybal

  2. Faculty of Applied Sciences, University of West Bohemia, Pilsen, Czech Republic

    Emanuel Makrlík

  3. Institute of Chemical Technology, Prague, Czech Republic

    Jan Budka & Petr Vaňura

Authors
  1. Jaroslav Kříž
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  2. Jiří Dybal
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  3. Emanuel Makrlík
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  4. Jan Budka
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  5. Petr Vaňura
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Corresponding author

Correspondence to Emanuel Makrlík.

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Kříž, J., Dybal, J., Makrlík, E. et al. Protonation of electroneutral p-tert-butylcalix[4]arenetetraacetic acid. Monatsh Chem 141, 19–22 (2010). https://doi.org/10.1007/s00706-009-0218-3

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  • DOI: https://doi.org/10.1007/s00706-009-0218-3

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