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Influence of water on the conformations and interactions within two choline chloride-based deep eutectic solvents: a density functional theory investigation

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Abstract

This work presents the study of the conformations of {[Choline][Chloride]:Phenol} ratio [1:2] and {[Choline][Chloride]:Glycolic acid} ratio [1:1] deep eutectic solvents in their isolated state and with the presence of water. The optimization of the geometries was carried out using density functional theory with the B3LYP functional and the 6–311(+ +)G(d,p) basis set. Through the study of the geometry optimization and the charge distribution, the most stable conformations of choline, choline chloride, the two aforementioned deep eutectic solvents and their cluster with water are detailed. The main hydrogen bonds are identified using the values of stabilizing energies between interacting orbitals. The results highlight the OH‧‧‧Cl type of hydrogen bonds as one of the key interactions. It is found that the chloride ion acts as a hydrogen bond acceptor while the choline ion acts primarily as a hydrogen bond donor. Glycolic acid and phenol can play both roles. The molecule of water is able to form various hydrogen bonds. The strongest hydrogen bonds are observed between the chloride ion and a hydroxyl group. Finally, an increasing total number of hydrogen bonds in a system decreases the strength of the overall interactions.

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All data generated or analyzed during this study are included in this published article and also in the supporting information file.

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This work was supported by the region Grand-Est.

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  1. Laboratoire Réactions et Génie des Procédés (UMR CNRS 7274), Université de Lorraine, Ecole Nationale Supérieure des Industries Chimiques, 1 rue Grandville, 54000, Nancy, France

    Thomas Di Pietro, Laetitia Cesari & Fabrice Mutelet

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Thomas Di Pietro: calculation, investigation, methodology, first draft. Laetitia Cesari: supervision, review. Fabrice Mutelet: supervision, project administration, writing—review and editing.

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Correspondence to Fabrice Mutelet.

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Di Pietro, T., Cesari, L. & Mutelet, F. Influence of water on the conformations and interactions within two choline chloride-based deep eutectic solvents: a density functional theory investigation. Struct Chem 34, 2165–2183 (2023). https://doi.org/10.1007/s11224-023-02156-6

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