Theoretical investigation of supramolecular hydrogen-bonded choline chloride-based deep eutectic solvents using density functional theory

Naseem, Zubera; Shehzad, Rao Aqil; Ihsan, Anaum; Iqbal, Javed; Zahid, Muhammad; Pervaiz, Amjad; Sarwari, Ghulam

doi:10.1016/j.cplett.2021.138427

Cited by 86 publications

(36 citation statements)

References 57 publications

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“…Recently, computational studies have been conducted, allowing further knowledge of the supramolecular structure of these eutectic mixtures, showing that the hydrogen bonds or even the Van der Waals interactions interfere with the capacity of the initial compounds to crystallize [ 28 ]. In particular, density functional theory (DFT) demonstrated that, in ChCl-based DES, the electronegative anion chloride is capable to provide more binding sites to form hydrogen bonds, and a competitive activity was observed between various HBD and choline cation [ 29 ]. In this scenario, the formation of hydrogen bonds and the consequent delocalization of charges, in addition to designing the three-dimensional network, significantly decreases the melting points of the different eutectic mixtures.…”

Section: Structure and Properties Of Choline Chloride-based Desmentioning

confidence: 99%

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

2021

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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.

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Section: Structure and Properties Of Choline Chloride-based Desmentioning

confidence: 99%

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

2021

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“…As for functionals, a lot of studies of systems containing no more than several dozen atoms have been performed using the hybrid B3LYP functional with 20% HF exchange in conjunction with the family of Pople's split-valence basis sets with the addition of a different number of diffuse and polarization functions (6-31G(d), 6-31G(d,p), 6-31+G(d,p)) [44,[47][48][49][50][51][52][53][54][55][56][57], and correlation-consistent basis sets with augmented diffuse functions aug-cc-PVDZ [58]. Some organic cations contain alkyl side chains and/or aromatic moieties with important contributions from dispersion forces and hence require a proper description.…”

Section: Dft-derived Peculiarities Of the Local Des Structurementioning

confidence: 99%

“…Another popular alternative is to use the meta-hybrid functional M06-2X with 54% HF exchange. It has been shown to have excellent performance and accuracy in systems where dispersion interactions contribute significantly to conformer energetics [50,[64][65][66][67][68][69][70]. Other functionals, for example hybrid long-range corrected CAM-B3LYP [50], hybrid PBE0 [50], hybrid PW91 [71] have also been used, albeit rarely.…”

Section: Dft-derived Peculiarities Of the Local Des Structurementioning

confidence: 99%

Section: Role Of the Hydrogen Bond Donormentioning

confidence: 99%

“…Polyols and acids have also received attention [50,209]. Naseem et al [50] used MD simulations to compare DESs based on polyols (ethylene glycol and glycerol) and acids (malic acid, tartaric acid and oxalic acid). The DES based on tartaric acid was found to be more stable due to the larger number of HBD groups in tartaric acid compared to other HBDs.…”

Section: Role Of the Hydrogen Bond Donormentioning

confidence: 99%

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Computer Simulations of Deep Eutectic Solvents. Challenges, Solutions, and Perspectives

Tolmachev¹,

Lukasheva²,

Рамазанов³

et al. 2021

Preprint

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Deep eutectic solvents (DESs) are one of the most rapidly evolving types of solvents, appearing in a broad range of applications such as nanotechnology, electrochemistry, biomass transformation, pharmaceuticals, membrane technology, biocomposite development, modern 3D-printing, and many others. The range of their applicability continues to expand, which demands the development of new DESs with improved properties. To do so requires an understanding of the fundamental relationship between the structure and properties of DESs. Computer simulation and machine learning techniques provide a fruitful approach as they can provide predictions, reveal physical mechanisms and readily be linked to experiments. This review is devoted to the computational research of DESs and describes technical features of DES simulations and the corresponding perspectives on various DES applications. The aim is to demonstrate the current frontiers of computational research of DESs and discuss future perspectives.

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Natural Eutectic Solvent Mixture of l‐Menthol/Malonic acid (4 : 1) and Its Ibuprofen Solution: Thermal and Physical Characterizations and NMR Studies of Molecular Interaction

et al. 2023

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A eutectic mixture of L-menthol and malonic acid, Me/MA (4 : 1), was characterized by calorimetry and other physical measurements. The new deep eutectic solvent (m.p. 6 °C) solvates 338 mg of ibuprofen per mL, and the solution is stable in a wide temperature range. Strategies of NMR titration used in supramolecular chemistry were employed to explore binding forces between the eutectic constituents as well as solutesolvent interaction in ibuprofen solution. Even in acetonitrile, Me 4 MA is formed through a hydrogen-bonding network, where the constituents act as hydrogen donors and acceptors at the same time. The estimated association constant is around 30 M À 1 ; the binding forces are enough to build the eutectic mixture at high concentrations. The aggregate Me 4 MA forms a molecular complex with ibuprofen in acetonitrile as a result of the cooperative effect of the constituents. In addition, van der Waals interactions are operative between ibuprofen and menthol in the saturated IB-Me/MA (4 : 1) solution.

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Theoretical investigation of supramolecular hydrogen-bonded choline chloride-based deep eutectic solvents using density functional theory

Cited by 86 publications

References 57 publications

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

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

Computer Simulations of Deep Eutectic Solvents. Challenges, Solutions, and Perspectives

Natural Eutectic Solvent Mixture of l‐Menthol/Malonic acid (4 : 1) and Its Ibuprofen Solution: Thermal and Physical Characterizations and NMR Studies of Molecular Interaction

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