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Density functional theory investigation of interactions between phenolic compounds and water or hydrophobic deep eutectic solvent

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Abstract

This study investigated the possibility to replace organic solvent by new type of green solvent (hydrophobic deep eutectic solvent) for the extraction of phenolic compounds by evaluating the interactions between phenolic compounds and water or hydrophobic deep eutectic solvent. With a comparison of both interactions, the ability of the solvent to extract targeted molecule can be predicted. First, study of molecular conformations of phenol, guaiacol, pyrocatechol and eugenol was performed using Density Functional Theory (DFT) with the model M06-2X and the basis set cc-pVTZ. Influence of water involved in {water-phenolic compound} clusters on electronegativity and hardness was investigated. In addition, hydrogen bonds involved in the hydrophobic deep eutectic solvent menthol: dodecanoic acid [2:1] were also evaluated. Finally, study of {hydrophobic deep eutectic solvent- phenol} cluster was performed. The results show that the interaction energy of the {phenol-HDES menthol: dodecanoic acid [2:1]} cluster (53.63 kcal.mol−1) is higher than the one calculated for {phenol-water} (35.26 kcal.mol−1) reflecting the ability of this HDES to extract phenol from water. Natural bond analysis (NBO) reports a strong stabilisation of hydrogen bonds involved in all systems. For the {phenol-HDES} cluster, the largest stabilisation energy (4 kcal.mol−1) is obtained for the hydrogen bond between the phenol and the carboxyl acid of the HDES. Frequency results show that this particular OH-bond is the most red-shifted in cluster in comparison with isolated form.

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Data Availability

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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  1. Université de Lorraine, CNRS, 54000, Nancy, LRGP, France

    Pierre-Alann Cablé, Yann Le Brech & Fabrice Mutelet

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  1. Pierre-Alann Cablé
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  2. Yann Le Brech
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  3. Fabrice Mutelet
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Pierre-Alann Cable: calculation, investigation, methodology. Yann Le Brech: supervision, review. Fabrice Mutelet: supervision, project administration, writing- review and editing. The final version of the manuscript submitted was approved by all the authors.

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Correspondence to Fabrice Mutelet.

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Cablé, PA., Le Brech, Y. & Mutelet, F. Density functional theory investigation of interactions between phenolic compounds and water or hydrophobic deep eutectic solvent. Struct Chem 35, 321–339 (2024). https://doi.org/10.1007/s11224-023-02180-6

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