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Preparation of Binary and Ternary Deep Eutectic Systems
Published on: October 31, 2019
Anatomy of a deep eutectic solvent: structural properties of choline chloride : sesamol 1 : 3 compared to reline
Matteo Busato1, Valentina Migliorati1, Alessandra Del Giudice1
1Department of Chemistry, University "La Sapienza", P.le A. Moro 5, 00185, Rome, Italy. p.dangelo@uniroma1.it.
Abstract:
The structural properties of the deep eutectic solvent (DES) formed by choline chloride (ChCl) and sesamol in 1 : 3 ratio have been investigated and compared to those of reline (ChCl : urea 1 : 2). An integrated approach combining small and wide angle X-ray scattering with molecular dynamics simulations has been employed and the simulation protocol has been validated against the experimental data. In the ChCl : sesamol DES, strong hydrogen bonds (HBs) are formed between the chloride anion and the hydroxyl groups of the choline and of sesamol molecules. Conversely, choline-choline, choline-sesamol and sesamol-sesamol interactions are negligible. A more extended interplay between the constituents is observed in reline where, besides the HBs involving the chloride anion, the eutectic formation is favored also by strong choline-urea and urea-urea interactions. The three-dimensional arrangement around the individual components shows that, in the ChCl : sesamol DES, the cholinium cations and the sesamol molecules are packed in such a way to maximize the interactions with the chlorine anion. This structural arrangement may favor the π-π interactions between the sesamol molecules and the aromatic species mediated by the chloride ions, providing an interpretation for the high separation rates previously observed for phenolic DESs towards aromatic compounds.
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