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Synthesis of Ionizable Calix[4]arenes for Chelation of Selected Divalent Cations


Blumberg, Markus; Al-Ameed, Karrar; Eiselt, Erik; Luber, Sandra; Mamat, Constantin (2022). Synthesis of Ionizable Calix[4]arenes for Chelation of Selected Divalent Cations. Molecules, 27(5):1478.

Abstract

Two sets of functionalised calix[4]arenes, either with a 1,3-crown ether bridge or with an open-chain oligo ether moiety in 1,3-position were prepared and further equipped with additional deprotonisable sulfonamide groups to establish chelating systems for selected cations Sr2+, Ba2+, and Pb2+ ions. To improve the complexation behaviour towards these cations, calix[4]arenes with oligo ether groups and modified crowns of different sizes were synthesized. Association constants were determined by UV/Vis titration in acetonitrile using the respective perchlorate salts and logK values between 3.2 and 8.0 were obtained. These findings were supported by the calculation of the binding energies exemplarily for selected complexes with Ba2+.
Keywords: calixarenes; barium; chelation

Abstract

Two sets of functionalised calix[4]arenes, either with a 1,3-crown ether bridge or with an open-chain oligo ether moiety in 1,3-position were prepared and further equipped with additional deprotonisable sulfonamide groups to establish chelating systems for selected cations Sr2+, Ba2+, and Pb2+ ions. To improve the complexation behaviour towards these cations, calix[4]arenes with oligo ether groups and modified crowns of different sizes were synthesized. Association constants were determined by UV/Vis titration in acetonitrile using the respective perchlorate salts and logK values between 3.2 and 8.0 were obtained. These findings were supported by the calculation of the binding energies exemplarily for selected complexes with Ba2+.
Keywords: calixarenes; barium; chelation

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Physical Sciences > Analytical Chemistry
Physical Sciences > Chemistry (miscellaneous)
Life Sciences > Molecular Medicine
Life Sciences > Pharmaceutical Science
Life Sciences > Drug Discovery
Physical Sciences > Physical and Theoretical Chemistry
Physical Sciences > Organic Chemistry
Uncontrolled Keywords:Chemistry (miscellaneous), Analytical Chemistry, Organic Chemistry, Physical and Theoretical Chemistry, Molecular Medicine, Drug Discovery, Pharmaceutical Science
Language:English
Date:22 February 2022
Deposited On:05 Jan 2023 12:50
Last Modified:28 Apr 2024 01:42
Publisher:MDPI Publishing
ISSN:1420-3049
OA Status:Gold
Free access at:Publisher DOI. An embargo period may apply.
Publisher DOI:https://doi.org/10.3390/molecules27051478
Project Information:
  • : FunderSwiss national science foundation
  • : Grant IDPP00P2_170667
  • : Project Title
  • Content: Published Version
  • Language: English
  • Licence: Creative Commons: Attribution 4.0 International (CC BY 4.0)