ChemInform Abstract: Hydrogen Bonding. Part 33. NMR Study of the Hydration of Choline and Acetylcholine Halides.

Harmon, Kenneth M.; Akin, Anne; Avci, Günsel F.; Nowos, Lydia S.; Tierney, Mary Beth

doi:10.1002/chin.199127041

Cited by 4 publications

(8 citation statements)

References 1 publication

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“…75 wt %. 39 In this work, we performed a similar experiment but adding D 2 O instead of H 2 O. The 1 H NMR spectrum of ChCl/2H 2 O exhibited one peak at 5.37 corresponding to the proton of the hydroxyl group of ChCl and another one at 4.41 ppm corresponding to H 2 O, being the integrals in agreement with the stoichiometry in which both compounds are combinede.g., 1H and 4H, respectively (Figure 2a).…”

Section: ■ Results and Discussionsupporting

confidence: 54%

“…In previous works reporting on the ChCl/2H 2 O case, the ChCl/2H 2 O content right before full exchange between the proton of the hydroxyl group of ChCl occurs was ca. 75 wt % . In this work, we performed a similar experiment but adding D 2 O instead of H 2 O.…”

Section: Results and Discussionmentioning

confidence: 99%

“…In particular, we studied the addition of further water to the ChCl/H 2 O liquid mixture with a 1:2 molar ratioe.g., ChCl/2H 2 O. This 1:2 molar ratio was close to the solubility limit of ChCl in H 2 O at 25 °Ce.g., 1.8and at reduced pressure, it crystallizes in the form of the dihydrated salt. , Finally, we also applied NMR and Brillouin spectroscopies to study the eutectic obtained upon addition of water to ZnCl 2 ·3H 2 O, as described elsewhere …”

Section: Introductionmentioning

confidence: 99%

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Brillouin Spectroscopy as a Suitable Technique for the Determination of the Eutectic Composition in Mixtures of Choline Chloride and Water

et al. 2020

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Deep eutectic solvents (DESs) resulting from the right combination between a hydrogen-bond donor (HBD) and a hydrogen-bond acceptor (HBA) are becoming quite popular in number of applications. More recently, natural DESs (NADESs) containing sugars, natural organic acids, and amino acids as HBDs and ChCl as HBA have received great attention because of their further environmental sustainability as compared to regular DESs. Within this context, mixing water in controlled amounts has been widely accepted as a simple and practical way of altering DES chemical and thermodynamic properties, with viscosity and conductivity experiencing the most significant changes. However, the number of papers describing eutectic mixtures with water as the only HBD is scarce and basically none has been done in fundamental terms. Herein, we investigated mixtures composed of water as the only HBD and ChCl as the HBA using differential scanning calorimetry (DSC) as well as 1 H nuclear magnetic resonance (NMR) and Brillouin spectroscopies. We found the aqueous dilution of ChCl/2H 2 O with a ChCl/2H 2 O content of ca. 80 wt % was an eutectic. Interestingly, this mixture could be considered a NADES according to its eutectic distance (ΔT me ), in range to eutectics obtained in aqueous dilutions of salt hydrates.

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Section: ■ Results and Discussionsupporting

confidence: 54%

Section: Results and Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Brillouin Spectroscopy as a Suitable Technique for the Determination of the Eutectic Composition in Mixtures of Choline Chloride and Water

et al. 2020

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“…54 DSC scans depicted in Figure S26 revealed this was actually the case for RUChCl11W, exhibiting a melting point below that of any of the samples (Figure 8) and thus suggesting the formation of new eutectic mixtures containing water within its composition. The appearance of more than one single melting was ascribed to the compositional diversity of the aqueous dilutions of RUChCl and the eventual combination of the four HBD/ HBA components as not only quaternary mixtures (e.g., RUChClW) but also binary (e.g., UW 55 or ChClW 56 ) or ternary (e.g., UChClW or RChClW) ones, as well as mixtures thereof.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Looking at the “Water-in-Deep-Eutectic-Solvent” System: A Dilution Range for High Performance Eutectics

López‐Salas

Vicent-Luna

Imberti

et al. 2019

ACS Sustainable Chem. Eng.

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Deep eutectic solvents (DESs) are lately expanding their use to more demanding applications upon aqueous dilution thanks to the preservation of the most appealing properties of the original DESs while overcoming some of their most important drawbacks limiting their performance, like viscosity. Both experimental and theoretical works have studied this dilution regime, the so-called “water-in-DES” system, at near-to stoichiometric amounts to the original DES. Herein, we rather studied the high-dilution range of the “water-in-DES” system looking for enhanced performance because of the interesting properties (a further drop of viscosity) and cost (water is cheap) that it offers. In particular, we found that, in the “water-in-DES” system of a ternary DES composed of resorcinol, urea and choline chloride (e.g., RUChClnW, where n represents mol of water per mole of ternary DES), the tetrahedral structure of water was distorted as a consequence of its incorporation, as an additional hydrogen bond donor or hydrogen bond acceptor, into the hydrogen bond complexes formed among the original DES components . DSC confirmed the formation of a new eutectic, with a melting point below that of its respective components, the original ternary DES and water. This depression in the melting point was also observed in the same regime of reline and malicine aqueous dilutions, thus suggesting the universality of this simple procedure (i.e., water addition to reach the high-dilution range of the “water-in-DES” system) to obtain deeper eutectics eventually providing enhanced performances and lower cost.

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“…In this concentration range, there is very little dissociation of ChCl and the liquid phase is composed essentially of ion pairs. 33 This can explain the near-ideal behavior since, under these conditions, the molecular interactions are dominated by hydrogen bonding, 33,66 and no longer by electrostatic interactions, and water can supply broken hydrogen bonding resulting from the dissolution of ChCl. Concerning the solid-liquid phase diagram, the eutectic point has been estimated to be at 204 K and the ChCl mole fraction close to 0.20.…”

Section: Thermodynamic Assessment Of the Liquid Phase Non-idealitymentioning

confidence: 99%

Extensive characterization of choline chloride and its solid–liquid equilibrium with water

Ferreira

Vilas-Boas

Silva

et al. 2022

Phys. Chem. Chem. Phys.

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ChemInform Abstract: Hydrogen Bonding. Part 33. NMR Study of the Hydration of Choline and Acetylcholine Halides.

Cited by 4 publications

References 1 publication

Brillouin Spectroscopy as a Suitable Technique for the Determination of the Eutectic Composition in Mixtures of Choline Chloride and Water

Brillouin Spectroscopy as a Suitable Technique for the Determination of the Eutectic Composition in Mixtures of Choline Chloride and Water

Looking at the “Water-in-Deep-Eutectic-Solvent” System: A Dilution Range for High Performance Eutectics

Extensive characterization of choline chloride and its solid–liquid equilibrium with water

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