Liquid structure of the choline chloride-urea deep eutectic solvent (reline) from neutron diffraction and atomistic modelling

Hammond, Oliver S.; Bowron, Daniel T.; Edler, Karen J.

doi:10.1039/c5gc02914g

Cited by 416 publications

(459 citation statements)

References 51 publications

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“…[27,28] Mass fraction of residual water was measured by using a coulometric Karl-Fisher titration (831KF CoulometerMetrohm and using Hydranal® Coulomat E solution from Fluka) for each sample and found in the order of 3-7 wt % depending on the DES.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

Diffusion of redox active molecules in deep eutectic solvents

Fryars

Limanton

Gauffre

et al. 2018

Journal of Electroanalytical Chemistry

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Classical electrochemical approaches were evaluated for investigating the basic properties of deep eutectic solvents (DES) with a special focus on the mass transport phenomena and diffusion of charged species in DES. Three classical DES were considered: Reline, Ethaline and cholinechloride-lactic acid mixture. Cyclic voltammetries of the ferrocene oxidation and of the ferricyanide reduction, respectively with charge 0 and -3, exhibit well-defined responses in these media. For all considered DES and redox molecules, diffusion processes govern the masstransport of the redox molecules from the solution to the electrode. Derived diffusion coefficients were extracted and found to present some inconstancies with the classical StokesEinstein law for homogeneous media. The diffusion coefficients were found to be almost unaffected by the charge present on the diffusing molecules contrarily to observations made for ionic liquids.

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Section: Accepted Manuscriptmentioning

confidence: 99%

Diffusion of redox active molecules in deep eutectic solvents

Fryars

Limanton

Gauffre

et al. 2018

Journal of Electroanalytical Chemistry

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“…The different stereoselectivities of the reaction observed in different DES phases could be related to the creation of different tridimensional networks between DES and L-proline, and thus of different chiral reaction environments possibly affecting the stereochemistry of the intermediate species involved in the catalytic cycle [41]. The equilibrating nature of the aldol reaction and the influence of such reversibility on its stereochemical outcome has recently been studied [42].…”

Section: Resultsmentioning

confidence: 99%

Towards the development of continuous, organocatalytic, and stereoselective reactions in deep eutectic solvents

Brenna¹,

Massolo²,

Puglisi³

et al. 2016

Beilstein J. Org. Chem.

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Different deep eutectic solvent (DES) mixtures were studied as reaction media for the continuous synthesis of enantiomerically enriched products by testing different experimental set-ups. L-Proline-catalysed cross-aldol reactions were efficiently performed in continuo, with high yield (99%), anti-stereoselectivity, and enantioselectivity (up to 97% ee). Moreover, using two different DES mixtures, the diastereoselectivity of the process could be tuned, thereby leading to the formation, under different experimental conditions, to both the syn- and the anti-isomer with very high enantioselectivity. The excess of cyclohexanone was recovered and reused, and the reaction could be run and the product isolated without the use of any organic solvent by a proper choice of DES components. The dramatic influence of the reaction media on the reaction rate and stereoselectivity of the process suggests that the intimate architecture of DESs deeply influences the reactivity of different species involved in the catalytic cycle.

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“…As proposed by Abbott, DESs can be divided into 4 categories which are based on hydrogen bonding interactions . Noncovalent interactions between hydrogen bond donor and acceptor hinder the crystallization of whole system . Such a class of emerging liquid has many desirable applications, including dissolving biomass, preparing materials, capturing carbon dioxide and so on .…”

Section: Figurementioning

confidence: 99%

“Inverted” Deep Eutectic Solvents Based on Host‐Guest Interactions

Mou

et al. 2019

Chemistry An Asian Journal

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Herein, the concept of “inverted” (the mode “molecules mainly interact with cations”) deep eutectic solvents (DESs) is proposed. A strategy to form inverted DESs by host‐guest interactions was developed, and thus numerous DESs could be designed and formed by a combination of host and guest molecules. These liquids are expected to be used as nonaqueous electrolytes in potassium‐ion batteries or other fields for further exploration.

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Liquid structure of the choline chloride-urea deep eutectic solvent (reline) from neutron diffraction and atomistic modelling

Abstract: The structure of 1 : 2 choline chloride : urea (reline) deep eutectic solvent has been determined, showing extensive hydrogen bonding between all species.

Cited by 416 publications

References 51 publications

Diffusion of redox active molecules in deep eutectic solvents

Diffusion of redox active molecules in deep eutectic solvents

Towards the development of continuous, organocatalytic, and stereoselective reactions in deep eutectic solvents

“Inverted” Deep Eutectic Solvents Based on Host‐Guest Interactions

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