An Integrated approach (thermodynamic, structural, and computational) to the study of complexation of alkali-metal cations by a lower-rim calix[4]arene amide derivative in acetonitrile

Inorganic Chemistry
Gordan HorvatVladislav Tomišić

Abstract

The calix[4]arene secondary-amide derivative L was synthesized, and its complexation with alkali-metal cations in acetonitrile (MeCN) was studied by means of spectrophotometric, NMR, conductometric, and microcalorimetric titrations at 25 °C. The stability constants of the 1:1 (metal/ligand) complexes determined by different methods were in excellent agreement. For the complexation of M(+) (M = Li, Na, K) with L, both enthalpic and entropic contributions were favorable, with their values and mutual relations being quite strongly dependent on the cation. The enthalpic and overall stability was the largest in the case of the sodium complex. Molecular and crystal structures of free L, its methanol and MeCN solvates, the sodium complex, and its MeCN solvate were determined by single-crystal X-ray diffraction. The inclusion of a MeCN molecule in the calixarene hydrophobic cavity was observed both in solution and in the solid state. This specific interaction was found to be stronger in the case of metal complexes compared to the free ligand because of the better preorganization of the hydrophobic cone to accept the solvent molecule. Density functional theory calculations showed that the flattened cone conformation (C(2) point group) o...Continue Reading

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Citations

Jan 20, 2016·The Journal of Physical Chemistry. a·Paul MurphyMartin J Paterson
Aug 30, 2017·Physical Chemistry Chemical Physics : PCCP·Gordan HorvatVladislav Tomišić
Mar 8, 2019·Chemical Communications : Chem Comm·Hans-Jörg Schneider
Jan 9, 2018·Organic & Biomolecular Chemistry·Nikola CindroVladislav Tomišić
Aug 15, 2017·The Journal of Physical Chemistry. B·Josip PožarVladislav Tomišić

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