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Calixarenes are a class of supramolecular ligands that can be readily functionalized to give very efficient and even selective receptors for various ionic and neutral chemical species.1,2 Among them, those bearing sulfur-based functional groups form stabile complexes with low-charge-density and soft metal cations.3 In the scope of this work, binding affinity of thioamide calix[4]arene derivative towards alkali, alkaline earth, and soft metal cations in acetonitrile was investigated by spectrophotometry, NMR spectroscopy, isothermal titration calorimetry, and X-ray crystallography. The obtained results were discussed regarding the structural characteristics of the ligand, as well the size, charge density, and polarizing power of the cations.
Keywords: calixarenes, metal cations, thermodynamics
References:
1 Gutsche, C. D.; Calixarenes: An Introduction, 2nd edition, The Royal Society of Chemistry, Cambridge, 2008.
2 a) Modrušan, M.; Cindro, N.; Usenik, A.; Leko, K.; Glazer, L.; Tomaš, R.; Horvat, G.; Požar, J.; Tomišić, V. Croat. Chem. Acta, 2024, 97, 1–15; b) Požar, J.; Cvetnić, M.; Usenik, A.; Cindro, N.; Horvat, G.; Leko, K.; Modrušan, M.; Tomišić, V. Molecules 2022, 27, 470; c) Leko, K.; Usenik, A.; Cindro, N.; Modrušan, M.; Požar, J.; Horvat, G.; Stilinović, V.; Hrenar, T.; Tomišić, V. ACS Omega, 2023, 8, 43074–43087; d) Cvetnić, M.; Cindro, N.; Bregović, N.; Tomišić, V. ACS Phys. Chem Au, 2024, 4, 6, 773–786.
3 a) Delaigue, X.; Harrowfield, J. McB.; Hosseini, M. W.; De Cian, A.; Fischer, J.; Kyritsakas, N. J. Chem. Soc., Chem. Commun. 1994, 1579; b) Danil de Namor, A. F.; Pawłowski, T. S.; New J. Chem. 2011, 35, 375–384; c) Śliwa, W. J. Incl. Phenom. Macrocycl. Chem. 2005, 52, 13–37.