Croatica Chemica Acta, Vol. 98 No. 2, 2025.
Original scientific paper
https://doi.org/10.5562/cca4146
Synthesis, Alkali Metal Cation Binding and Computational Analysis of Adamantane-substituted Hexaaza Crown Ethers
Tatjana Šumanovac
; Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, Croatia
Mihaela Jakić
orcid.org/0009-0003-8133-2655
; Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, Croatia
Kata Mlinarić-Majerski
; Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, Croatia
*
Marina Šekutor
orcid.org/0000-0003-1629-3672
; Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, Croatia
*
* Corresponding author.
Supplements: cca4146_Supplement.pdf
Abstract
We prepared a so far unknown class of hexaaza crown ethers substituted with six adamantyl side-arms and used them for extraction of alkali metal cations from an aqueous medium. These host molecules were designed to take advantage of intramolecular London dispersion interactions in order to tune the host's structural organization and enhance its binding capability. The studied adamantyl hexaaza crown ethers all showed efficient extraction capabilities for alkali metal cations, unlike the parent hexaaza-18-crown-6. The experimental study was supported by a computational analysis and a global minima structure search afforded geometries that highlighted the importance of non-covalent interactions for complex formation and adoption of specific molecular conformations. In addition, the obtained binding energies for complex formation further supported our experimental findings. This new class of alkali metal cation binding hosts could find future application in bioactivity studies that apply supramolecular recognition processes.
Keywords
hexaaza crown ethers; adamantane; alkali metal cations; extraction experiments; London dispersion; conformer search
Hrčak ID:
327446
URI
Publication date:
3.2.2025.
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