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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 id 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 id orcid.org/0000-0003-1629-3672 ; Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, Croatia *

* Corresponding author.


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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

https://hrcak.srce.hr/327446

Publication date:

3.2.2025.

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