The Role of Triazole and Glucose Moieties in Alkali Metal Cation Complexation by Lower-Rim Tertiary-Amide Calix[4]arene Derivatives

Požar, Josip; Cvetnić, Marija; Usenik, Andrea; Cindro, Nikola; Horvat, Gordan; Leko, Katarina; Modrušan, Matija; Tomišić, Vladislav

doi:10.3390/molecules27020470

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The Role of Triazole and Glucose Moieties in Alkali Metal Cation Complexation by Lower-Rim Tertiary-Amide Calix[4]arene Derivatives

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Department of Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, 10000 Zagreb, Croatia

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Academic Editor: Carmine Gaeta

Molecules 2022, 27(2), 470; https://doi.org/10.3390/molecules27020470

Received: 17 December 2021 / Revised: 5 January 2022 / Accepted: 6 January 2022 / Published: 12 January 2022

(This article belongs to the Special Issue Physicochemical and Structural Aspects of Calixarene Chemistry)

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Abstract

The binding of alkali metal cations with two tertiary-amide lower-rim calix[4]arenes was studied in methanol, N,N-dimethylformamide, and acetonitrile in order to explore the role of triazole and glucose functionalities in the coordination reactions. The standard thermodynamic complexation parameters were determined microcalorimetrically and spectrophotometrically. On the basis of receptor dissolution enthalpies and the literature data, the enthalpies for transfer of reactants and products between the solvents were calculated. The solvent inclusion within a calixarene hydrophobic basket was explored by means of ¹H NMR spectroscopy. Classical molecular dynamics of the calixarene ligands and their complexes were carried out as well. The affinity of receptors for cations in methanol and N,N-dimethylformamide was quite similar, irrespective of whether they contained glucose subunits or not. This indicated that sugar moieties did not participate or influence the cation binding. All studied reactions were enthalpically controlled. The peak affinity of receptors for sodium cation was noticed in all complexation media. The complex stabilities were the highest in acetonitrile, followed by methanol and N,N-dimethylformamide. The solubilities of receptors were greatly affected by the presence of sugar subunits. The medium effect on the affinities of calixarene derivatives towards cations was thoroughly discussed regarding the structural properties and solvation abilities of the investigated solvents. View Full-Text

Keywords: calix[4]arenes; alkali metal cations; complexation; solvation; calorimetry; molecular dynamics

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Požar, J.; Cvetnić, M.; Usenik, A.; Cindro, N.; Horvat, G.; Leko, K.; Modrušan, M.; Tomišić, V. The Role of Triazole and Glucose Moieties in Alkali Metal Cation Complexation by Lower-Rim Tertiary-Amide Calix[4]arene Derivatives. Molecules 2022, 27, 470. https://doi.org/10.3390/molecules27020470

AMA Style

Požar J, Cvetnić M, Usenik A, Cindro N, Horvat G, Leko K, Modrušan M, Tomišić V. The Role of Triazole and Glucose Moieties in Alkali Metal Cation Complexation by Lower-Rim Tertiary-Amide Calix[4]arene Derivatives. Molecules. 2022; 27(2):470. https://doi.org/10.3390/molecules27020470

Chicago/Turabian Style

Požar, Josip, Marija Cvetnić, Andrea Usenik, Nikola Cindro, Gordan Horvat, Katarina Leko, Matija Modrušan, and Vladislav Tomišić. 2022. "The Role of Triazole and Glucose Moieties in Alkali Metal Cation Complexation by Lower-Rim Tertiary-Amide Calix[4]arene Derivatives" Molecules 27, no. 2: 470. https://doi.org/10.3390/molecules27020470

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The Role of Triazole and Glucose Moieties in Alkali Metal Cation Complexation by Lower-Rim Tertiary-Amide Calix[4]arene Derivatives

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