Solution- and gas-phase study of binding of ammonium and bisammonium hydrocarbons to oxacalix[4]arene carboxylate
Cowart, A., Brük, M.-L., Žoglo, N., Roithmeyer, H., Uudsemaa, M., Trummal, A., Selke, K., Aav, R., Kalenius, E., & Adamson, J. (2023). Solution- and gas-phase study of binding of ammonium and bisammonium hydrocarbons to oxacalix[4]arene carboxylate. RSC Advances, 13(2), 1041-1048. https://doi.org/10.1039/d2ra07614d
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RSC AdvancesAuthors
Date
2023Discipline
Analyyttinen kemiaNanoscience CenterOrgaaninen kemiaAnalytical ChemistryNanoscience CenterOrganic ChemistryCopyright
© 2023 The Author(s). Published by the Royal Society of Chemistry
Oxacalixarenes represent a distinctive class of macrocyclic compounds, which are closely related to the parent calixarene family, offering binding motifs characteristic of calixarenes and crown ethers. Nevertheless, they still lack extensive characterization in terms of molecular recognition properties and the subsequent practical applicability. We present here the results of binding studies of an oxacalix[4]arene carboxylate macrocycle toward a variety of organic ammonium cationic species. Our results show that the substituents attached to the guest ammonium compound largely influence the binding strengths of the host. Furthermore, we show that the characteristic binding pattern changes upon transition from the gas phase to solution in terms of the governing intermolecular interactions. We identify the key factors affecting host–guest binding efficacy and suggest rules for the important molecular structural motifs of the interacting parts of ammonium guest species and the macrocycle to facilitate sensing of ammonium cations.
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Royal Society of Chemistry (RSC)ISSN Search the Publication Forum
2046-2069Publication in research information system
https://converis.jyu.fi/converis/portal/detail/Publication/164981843
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The authors gratefully acknowledge financial support by the Ministry of Education and Research, Republic of Estonia (grants PSG400, PRG661 and PRG399) and European Regional Development Fund (project TK134 “EQUITANT” and Center of Excellence in Molecular Cell Engineering TK143), and instrumentation of University of Jyväskylä.License
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