Hydrogen bonds in aqueous choline chloride solutions by DFT calculations and X-ray scattering

Chai, Keke; Lü, Xingmei; Zhou, Yongquan; Liu, Hongyan; Wang, Guangguo; Jing, Zhuanfang; Zhu, Fayan; Liang, Han

doi:10.1016/j.molliq.2022.119742

Cited by 10 publications

(11 citation statements)

References 49 publications

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“…45 Meanwhile, it is consistent with our previous DFT calculations and Raman spectra results. 46 As Fig. 2b shows, Cl À forms a strong hydrogen bond with AA/ FA.…”

Section: Dft Calculationsmentioning

confidence: 92%

Structure of choline chloride-carboxylic acid deep eutectic solvents by wide-angle X-ray scattering and DFT calculations

Chai

Zhou

Lü

et al. 2023

Phys. Chem. Chem. Phys.

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“…45 Meanwhile, it is consistent with our previous DFT calculations and Raman spectra results. 46 As Fig. 2b shows, Cl À forms a strong hydrogen bond with AA/ FA.…”

Section: Dft Calculationsmentioning

confidence: 92%

Structure of choline chloride-carboxylic acid deep eutectic solvents by wide-angle X-ray scattering and DFT calculations

Chai

Zhou

Lü

et al. 2023

Phys. Chem. Chem. Phys.

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“…Another interesting issue, closely related to what has just been described, is the evaluation of the optimal amount of water required for the preparation of NADES solutions. The water content can vary from 10% up to 70% w/w (Chai et al, 2022). High water content can lead to reduced extraction as water molecules competition with the NADES components will lead to their H bonding disruption and the disruption of the NADES supramolecular structure; this can hinder their interaction with the plant cell wall resulting in reduce extraction capacity.…”

Section: Introductionmentioning

confidence: 99%

Extraction of phenolic compounds from spent coffee ground using natural deep eutectic solvents: New modeling approach

Bassani,

García‐Roldán,

Spigno

et al. 2024

J Food Process Engineering

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The extraction of bioactive compounds from food wastes or by‐products with natural deep eutectic solvents (NADES) could be an attractive alternative to traditional hydroalcoholic extraction but needs to be optimized taking advantage of modeling. This work aims to propose, develop, and discuss a new model for the extraction of phenolic compounds from spent coffee grounds (SCGs) using NADES to overcome some gaps related to the kinetic extraction models and the surface response methodology. The model presented is based on the same assumption as the kinetic model, but improving it to be able to predict phenolic extraction changing different process parameters (e.g., water content, time of extraction, temperature, etc.) using betaine: triethylene glycol (molar ratio 1:2). The model was validated on the extraction of total phenolic compounds from SCG as a function of water content of NADES ranging from 30 to 60% v/v. There was good agreement between experimental and simulated data and even, in some cases, better than with the second‐order kinetic models. In addition, the new model needs fewer parameters to be regressed concerning the specific case investigated in this work. This model and methodology can be the basis for further modeling applicable to other bioactives, and/or other NADES and feedstocks.Practical ApplicationsNatural deep eutectic solvents (NADES) can be a potential sustainable solvent for the valorization of food by‐products as they can be used to extract bioactive compounds with high added value. This extraction process needs to be optimized depending on several factors like water content in NADES solution, solids ratio, extraction time, and temperature. The model validated in this work on spent coffee ground (SCG) could be used for this purpose, improving the gaps related to the kinetic extraction models and the surface response methodology (RSM). The new model enables predicting the behavior of the process as a function of the parameters previously mentioned and reduces the number of experimental trials required compared with RSM. In particular, the new model was validated on the variation of water content in NADES solution. Certainly, this model will need to be further validated, but, once further studies are conducted, this model could be used for scale‐up calculation and design optimization of the industrial process.

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“…69 Therefore, the structural relaxation of ChCl due to the hydrogen bond donor−acceptor interactions results in the formation of anticonformer Ch + ions in relatively dilute mixtures. 66 It is interesting that as the concentration of ChCl in the mixture increases and reaches supersaturated states (3:1 and 5:1), the anticonformer peak near 760 cm −1 disappears and the gauche peak at 715 cm −1 dominates. Due to the crystalline-dominated phase of these supersaturated mixtures (Figure S8), the major contribution to the obtained Raman signal is from the ChCl crystal.…”

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confidence: 98%

“…It is clearly noticeable in Figure a that the small peak near 760 cm –1 emerges in relatively dilute mixtures (1:3, 1:2, and 1:1). Notably, the 760 cm –1 feature does not belong to characteristic vibrations of pure ChCl or Gly but arises from the C–N stretching mode of the anticonformer, as opposed to the strong N–C 4 symmetric stretch of the gauche-conformer at ∼715 cm –1 . , This anticonformer peak of Ch + has been observed in aqueous solutions of ChCl and choline dihydrogen phosphate ([Ch][DHP]) salts as well. − The intensity ratios of anti (760 cm –1 ) to gauche (715 cm –1 ) versus mixing ratio of ChCl:Gly are displayed in Figure .…”

mentioning

confidence: 99%

“…It is known that Cl – can also act as a hydrogen bond bridge between Ch + and Gly . Therefore, the structural relaxation of ChCl due to the hydrogen bond donor–acceptor interactions results in the formation of anticonformer Ch + ions in relatively dilute mixtures . It is interesting that as the concentration of ChCl in the mixture increases and reaches supersaturated states (3:1 and 5:1), the anticonformer peak near 760 cm –1 disappears and the gauche peak at 715 cm –1 dominates.…”

mentioning

confidence: 99%

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Interfacial Nanostructure and Hydrogen Bond Networks of Choline Chloride and Glycerol Mixtures Probed with X-ray and Vibrational Spectroscopies

Kim,

Weeraratna,

Nemšák

et al. 2024

J. Phys. Chem. Lett.

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The molecular distribution at the liquid−vapor interface and evolution of the hydrogen bond interactions in mixtures of glycerol and choline chloride are investigated using X-ray photoelectron spectroscopy (XPS) and Raman spectroscopy. Nanoscale depth profiles of supersaturated deep eutectic solvent (DES) mixtures up to ∼2 nm measured by ambientpressure XPS show the enhancement of choline cation (Ch + ) concentration by a factor of 2 at the liquid−vapor interface compared to the bulk. In addition, Raman spectral analysis of a wide range of DES mixtures reveals the conversion of gauche-conformer Ch + into the anti-conformer in relatively lower ChCl concentrations. Finally, the depletion of Ch + from the interface (probing depth = 0.4 nm) is demonstrated by aerosol-based velocity map imaging XPS measurements of glyceline and water mixtures. The nanostructure of liquid−vapor interfaces and structural rearrangement by hydration can provide critical insight into the molecular origin of the deep eutectic behavior and gas-capturing application of DESs.

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Hydrogen bonds in aqueous choline chloride solutions by DFT calculations and X-ray scattering

Cited by 10 publications

References 49 publications

Structure of choline chloride-carboxylic acid deep eutectic solvents by wide-angle X-ray scattering and DFT calculations

Structure of choline chloride-carboxylic acid deep eutectic solvents by wide-angle X-ray scattering and DFT calculations

Extraction of phenolic compounds from spent coffee ground using natural deep eutectic solvents: New modeling approach

Interfacial Nanostructure and Hydrogen Bond Networks of Choline Chloride and Glycerol Mixtures Probed with X-ray and Vibrational Spectroscopies

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