A1 Journal article (refereed)
Solution- and gas-phase study of binding of ammonium and bisammonium hydrocarbons to oxacalix[4]arene carboxylate (2023)

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

JYU authors or editors

Publication details

All authors or editors: Cowart, Anna; Brük, Mari-Liis; Žoglo, Nikita; Roithmeyer, Helena; Uudsemaa, Merle; Trummal, Aleksander; Selke, Kaspar; Aav, Riina; Kalenius, Elina; Adamson, Jasper

Journal or series: RSC Advances

eISSN: 2046-2069

Publication year: 2023

Volume: 13

Issue number: 2

Pages range: 1041-1048

Publisher: Royal Society of Chemistry (RSC)

Publication country: United Kingdom

Publication language: English

DOI: https://doi.org/10.1039/d2ra07614d

Publication open access: Openly available

Publication channel open access: Open Access channel

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/84965

Abstract

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.

Keywords: organic chemistry; molecules; organic compounds

Contributing organizations

Ministry reporting: Yes

VIRTA submission year: 2023

JUFO rating: 1