Synthesis, Alkali Metal Cation Binding and Computational Analysis of Adamantane-substituted Hexaaza Crown Ethers

Šumanovac Ramljak, Tatjana; Jakić, Mihaela; Mlinarić-Majerski, Kata; Šekutor, Marina (2025) Synthesis, Alkali Metal Cation Binding and Computational Analysis of Adamantane-substituted Hexaaza Crown Ethers. Croatica Chemica Acta, 98 (2). ISSN 0011-1643

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Official URL: http://doi.org/10.5562/cca4146

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.

Item Type:

Article

Uncontrolled Keywords:

hexaaza crown ethers; adamantane; alkali metal cations; extraction experiments; London dispersion; conformer search

Subjects:

NATURAL SCIENCES > Chemistry > Organic Chemistry

Divisions:

Division of Organic Chemistry and Biochemistry

Projects: