scholarly journals Choline Chloride-Based DES as Solvents/Catalysts/Chemical Donors in Pharmaceutical Synthesis

Molecules ◽  
2021 ◽  
Vol 26 (20) ◽  
pp. 6286
Author(s):  
Rosa Amoroso ◽  
Frank Hollmann ◽  
Cristina Maccallini
Keyword(s):  
Hydrogen Bond ◽  
Recent Literature ◽  
Choline Chloride ◽  
Pharmaceutical Compounds ◽  
Freezing Points ◽  
Eutectic Mixtures ◽  
Hydrogen Bond Interactions ◽  
The Individual ◽  
Water Dilution ◽  
Interactions Network

DES are mixtures of two or more compounds, able to form liquids upon mixing, with lower freezing points when compared to the individual constituents (eutectic mixtures). This attitude is due to the specific hydrogen-bond interactions network between the components of the mixture. A notable characteristic of DES is the possibility to develop tailor-made mixtures by changing the components ratios or a limited water dilution, for special applications, making them attractive for pharmaceutical purposes. In this review, we focused our attention on application of ChCl-based DES in the synthesis of pharmaceutical compounds. In this context, these eutectic mixtures can be used as solvents, solvents/catalysts, or as chemical donors and we explored some representative examples in recent literature of such applications.

scholarly journals Doubly ionic hydrogen bond interactions within the choline chloride–urea deep eutectic solvent

2016 ◽  
Vol 18 (27) ◽  
pp. 18145-18160 ◽  
Author(s):  
Claire R. Ashworth ◽  
Richard P. Matthews ◽  
Tom Welton ◽  
Patricia A. Hunt
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Computational Analysis ◽  
Choline Chloride ◽  
Deep Eutectic Solvent ◽  
Hydrogen Bond Interactions

Computational analysis indicates flexibility and diversity in the hydrogen bonding, but limited charge delocalisation, within the choline chloride–urea eutectic.

scholarly journals Delignification of unbleached pulp by ternary deep eutectic solvents

2021 ◽  
Vol 10 (1) ◽  
pp. 666-676
Author(s):  
Veronika Majová ◽  
Michal Jablonský ◽  
Marek Lelovský
Keyword(s):  
Hydrogen Bond ◽  
Lactic Acid ◽  
Lignin Content ◽  
Choline Chloride ◽  
Deep Eutectic Solvents ◽  
Kappa Number ◽  
Molar Ratios ◽  
The Individual ◽  
Low Solubility ◽  
Unbleached Pulp

Abstract The processing of lignocellulosic materials is very limited because of their low solubility in water and some organic solvents. Fifteen ternary deep eutectic solvents (DESs) were prepared and tested as solvents suitable for delignification of unbleached pulp. The selected ternary DESs are composed of quaternary ammonium salts and amino acids as hydrogen-bond acceptors, and organic acids and polyvalent alcohols as hydrogen bond donors, with molar ratios varying for the individual components. The delignification efficiency is significantly influenced by the degree of penetration of the solvent into the pulp fibre structure. Therefore, the density and viscosity analysis of individual solvents was performed. Unbleached beech pulp with initial kappa number 13.9 was treated with the prepared DESs. The kappa number indicates the residual lignin content or the bleachability of pulp. The efficiency of the solvents ranged from 1.4% to 28.1%. The most suitable for the pretreatment of fibres, based on lignin removal efficiency, were found to be three DESs, in the following order: malonic acid/choline chloride/1,3-propanediol (1:1:3) > choline chloride/acetamide/lactic acid (1:2:3) > choline chloride/urea/lactic acid (1:2:3).

scholarly journals Deliquescence Behavior of Deep Eutectic Solvents

2021 ◽  
Vol 11 (4) ◽  
pp. 1601
Author(s):  
Henrik Palmelund ◽  
Jukka Rantanen ◽  
Korbinian Löbmann
Keyword(s):  
Hydrogen Bond ◽  
Room Temperature ◽  
Deep Eutectic Solvents ◽  
Storage Conditions ◽  
Ambient Conditions ◽  
Hydrogen Bond Donor ◽  
Eutectic Melting ◽  
Melting Temperatures ◽  
Hydrogen Bond Interactions ◽  
The Individual

Deep eutectic solvents (DESs) are formed by a hydrogen bond donor and an acceptor. The hydrogen bond interactions between these two components significantly depress the melting temperature of the mixture. DESs have been used as an alternative for organic solvents in various branches of the chemical industry. Many DESs are very hygroscopic and water is known to change the properties of DESs, but there has neven been a systematic study performed on the deliquesence behavior of DESs. Therefore, this study investigated the thermal and deliquescent behavior of four DESs. The DES mixtures were stored in desiccators at different relative humidities (RH) to investigate the critical RH (RH0) for deliquescence. It was found that, due to the formation of a eutonic mixture, the RH0 to induce deliquescence for a given DES mixture was lower compared to the individual components comprising the DES. The results showed that, even though all investigated DESs had eutectic melting temperatures above room temperature, but due to the low RH0, they were able to appear liquid at room temperature under ambient conditions. The eutonic and eutectic compositions were identified at different compositions for the DESs. The results emphasize that great care must be taken to control the process and storage conditions for DESs.

scholarly journals Choline Chloride Based Natural Deep Eutectic Solvents as Extraction Media for Extracting Phenolic Compounds from Chokeberry (Aronia melanocarpa)

Molecules ◽  
2020 ◽  
Vol 25 (7) ◽  
pp. 1619 ◽  
Author(s):  
Maša Islamčević Razboršek ◽  
Milena Ivanović ◽  
Peter Krajnc ◽  
Mitja Kolar
Keyword(s):  
Hydrogen Bond ◽  
Phenolic Compounds ◽  
Choline Chloride ◽  
Dry Weight ◽  
Deep Eutectic Solvents ◽  
Ultrasound Assisted Extraction ◽  
Hydrogen Bond Acceptor ◽  
Mean Values ◽  
Natural Deep Eutectic Solvents ◽  
The Individual

For the isolation of selected phenolic compounds from dried chokeberries, natural deep eutectic solvents (NADESs) were investigated as a green alternative to conventionally used extraction solvents. Four types of NADESs were synthesised, with choline chloride as the hydrogen bond acceptor in combination with different hydrogen bond donors (sugars, organic acid and urea). Ultrasound-assisted extraction was used to improve the extractability of the phenolic compounds and the results were compared to those obtained with 80% methanol as the extraction media. The highest values of total phenols and total flavonoids were found in the extract obtained with choline chloride–fructose NADES (36.15 ± 3.39 mg gallic acid g−1 dry weight (DW) and 4.71 ± 0.33 mg rutin g−1 DW, respectively). The extraction recoveries for the individual phenolic compounds depended strongly on the phenolic compound’s structure, with relative mean values between 70% and 97%.

scholarly journals Processing of Functional Composite Resins Using Deep Eutectic Solvent

Crystals ◽  
2020 ◽  
Vol 10 (10) ◽  
pp. 864 ◽  
Author(s):  
Jing Xue ◽  
Jing Wang ◽  
Daoshuo Feng ◽  
Haofei Huang ◽  
Ming Wang
Keyword(s):  
Hydrogen Bond ◽  
Deep Eutectic Solvent ◽  
Deep Eutectic Solvents ◽  
Composite Resins ◽  
Polymeric Systems ◽  
Functional Composite ◽  
Hydrogen Bond Interactions ◽  
Green Production ◽  
The Individual ◽  
Economical Feasibility

Deep eutectic solvents (DESs)—a promising class of alternatives to conventional ionic liquids (ILs) that have freezing points lower than the individual components—are typically formed from two or more components through hydrogen bond interactions. Due to the remarkable advantages of biocompatibility, economical feasibility and environmental hospitality, DESs show great potentials for green production and manufacturing. In terms of the processing of functional composite resins, DESs have been applied for property modifications, recyclability enhancement and functionality endowment. In this review, the applications of DESs in the processing of multiple functional composite resins such as epoxy, phenolic, acrylic, polyester and imprinted resins, are covered. Functional composite resins processed with DESs have attracted much attention of researchers in both academic and industrial communities. The tailored properties of DESs for the design of functional composite resins—as well as the effects of hydrogen bond on the current polymeric systems—are highlighted. In addition to the review of current works, the future perspectives of applying DESs in the processing of functional composite resins are also presented.

Anion effect on alkali ion-crown complex formation in a moderately concentrated solutions: A sensitive probe of hidden interionic interactions operating in dissociating protic solvents

1990 ◽  
Vol 55 (5) ◽  
pp. 1149-1161
Author(s):  
Jiří Závada ◽  
Václav Pechanec ◽  
Oldřich Kocián
Keyword(s):  
Hydrogen Bond ◽  
Complex Formation ◽  
Charge Density ◽  
Macrocyclic Ligand ◽  
Simple Explanation ◽  
Anion Effect ◽  
Protic Solvents ◽  
The Individual ◽  
Alkali Salts ◽  
Alkali Ion

A powerful anion effect destabilizing alkali ion-crown complex formation has been found to operate in moderately concentrated protic (H2O, CH3OH, C2H5OH) solution, following the order HO- > AcO- > Cl- > Br- > NO3- > I- > NCS-. Evidence is provided that the observed effect does not originate from ion-pairing. A simple explanation is provided in terms of concordant hydrogen bond bridges of exalted stability between the gegenions, M+···OR-H···(OR-H)n···OR-H···A-. It is proposed that encapsulation of alkali ion by the macrocyclic ligand leads to a dissipation of the cation charge density destroying its ability to participate in the hydrogen bond bridge. An opposition against the alkali ion-crown complex formation arises accordingly in the solution in dependence on strength of the hydrogen bridge; for a given cation, the hydrogen bond strength increases with increasing anion charge density from NCS- to HO-(RO-). It is pointed out, at the same time, that the observed anion effect does not correlate with the known values of activity coefficients of the individual alkali salts which are almost insensitive to anion variation under the investigated conditions. As a resolution of the apparent paradoxon it is proposed that, in absence of the macrocyclic ligand, the stabilizing (concordant) bonding between the gegenions is nearly balanced by a destabilizing (discordant) hydrogen bonding between the ions of same charge (co-ions). Intrinsic differences among the individual salts are thus submerged in protic solvents and become apparent only when the concordant bonding is suppressed in the alkali ion-crown complex formation.

scholarly journals Bis[2-(2-hydroxymethyl)pyridine-κ2N,O](pivalato-κO)copper(II)

2012 ◽  
Vol 68 (8) ◽  
pp. m1055-m1055 ◽  
Author(s):  
M. Mobin Shaikh ◽  
Veenu Mishra ◽  
Priti Ram ◽  
Anil Birla
Keyword(s):  
Hydrogen Bond ◽  
Crystal Packing ◽  
Octahedral Geometry ◽  
Title Complex ◽  
Distorted Octahedral Geometry ◽  
Pyridine Ligands ◽  
Hydrogen Bond Interactions ◽  
Distorted Octahedral

The structure of the centrosymmetric title complex, [Cu(C5H9O2)2(C6H7NO)2], has the CuIIatom on a centre of inversion. The CuIIatom is six-coordinate with a distorted octahedral geometry, defined by the N and O atoms of the chelating 2-(2-hydroxymethyl)pyridine ligands and two carboxylate O atoms from two monodentate pivalate ions. The crystal packing is stabilized by intermolecular C—H...O and intramolecular O—H...O hydrogen-bond interactions.

Rietveld refinement of the cocrystal 2,4-dihydroxybenzoic acid–N′-(propan-2-ylidene)nicotinohydrazide (1/1)

2012 ◽  
Vol 68 (9) ◽  
pp. o335-o337 ◽  
Author(s):  
Saul H. Lapidus ◽  
Andreas Lemmerer ◽  
Joel Bernstein ◽  
Peter W. Stephens
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Powder Diffraction ◽  
Supramolecular Assembly ◽  
Covalent Bond ◽  
Analytical Tool ◽  
Powder Diffraction Data ◽  
Dihydroxybenzoic Acid ◽  
Bond Forming ◽  
Hydrogen Bond Interactions

A further example of using a covalent-bond-forming reaction to alter supramolecular assembly by modification of hydrogen-bonding possibilities is presented. This concept was introduced by Lemmerer, Bernstein & Kahlenberg [CrystEngComm(2011),13, 55–59]. The title structure, C9H11N3O·C7H6O4, which consists of a reacted niazid molecule,viz.N′-(propan-2-ylidene)nicotinohydrazide, and 2,4-dihydroxybenzoic acid, was solved from powder diffraction data using simulated annealing. The results further demonstrate the relevance and utility of powder diffraction as an analytical tool in the study of cocrystals and their hydrogen-bond interactions.

Sign in / Sign up

Export Citation Format

Share Document