Big data for a deep problem: Understanding the formation of NADES through comprehensive chemical analysis and RDKit

Ayres, Lucas B.; Weavil, Grayson; Alhoubani, Mays; Guinati, Barbara G.S.; Garcia, Carlos D.

doi:10.1016/j.molliq.2023.122891

Cited by 6 publications

(8 citation statements)

References 72 publications

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“…Additionally, the commonly implemented HBD-HBA combinations for the preparation of NADESs have been compiled in Table 3. [28][29][30] The development of NADES has primarily relied on empirical approaches, lacking comprehensive predictive models. Consequently, the synthesis of new NADES often involves trial-and-error methods, which can be time-consuming and costly.…”

Section: Components and Methodology Used For Nadesmentioning

confidence: 99%

Natural Deep Eutectic Solvents (NADES): Manufacture, Characteristics, and Their Significance as Designer Solvents

Satija,

Chambyal,

Singh

et al. 2024

ChemistrySelect

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To replace the hazardous organic solvents currently in use, one of the key objectives of green chemistry has been the development of green solvents obtained from natural sources. Natural deep eutectic solvents (NADES) are bio‐based natural compounds, namely primary metabolites like organic acids, sugar, alcohols, amines, and amino acids, which are acceptable to the environment and may eventually replace the conventionally used harsh organic solvents. This study focuses on the recent developments in the realm of these innovative materials as well as the conventional deep eutectic solvents (DES)‐based techniques. A more in‐depth examination of DES's applications in various chemical processes is covered after a description of its definition, manufacture, and unique characteristics. Their significance as designer solvents in various organic reactions and their impact on production methods are addressed.

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Section: Components and Methodology Used For Nadesmentioning

confidence: 99%

Natural Deep Eutectic Solvents (NADES): Manufacture, Characteristics, and Their Significance as Designer Solvents

Satija,

Chambyal,

Singh

et al. 2024

ChemistrySelect

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“…We believe this increase (up to 40 K) can be directly related to the elevated number of chlorine-based compounds present in the chemical database (rather than the effect of chloride itself), which is also in line with the relative number of reported DESs based on these compounds, as previously noted. 6 In this sense, considering the high MP of choline-based species (∼550 K), it becomes evident that the presence of those species significantly influences the MP predicted by the eutXG.…”

Section: Distribution Of the Residuals And Outliersmentioning

confidence: 98%

“…Deep eutectic solvents (DES) are mixtures of Lewis or Brønsted acids and bases that, upon mild heating or grinding, form a transparent mixture that remains liquid at a given temperature, at which at least one of the components would be a solid . Among the thousands of examples published, − DES featuring a melting point (MP) below room temperature are the most interesting as they have the potential to replace both traditional solvents and ionic liquids in room-temperature applications. Moreover, and as recently described by our group, the broad chemical diversity of the components has allowed researchers to make DESs with a broad range of chemical and physical properties, enabling unique applications in extractions, , reaction media, , sensors, , drug delivery, , mass conversion, , biology, , and environmental remediation. , Chemically speaking, DES are supported by a delicate interplay of intermolecular forces that include electrostatic interactions, hydrophobic interactions, van der Waals, , and (probably most importantly) hydrogen bonding. − While some reports suggest that some of the properties of DES can be modulated by the addition of water, − it is absolutely clear that many of those properties are determined by the balance of intermolecular interactions, which are (in turn) determined by the structure and functional groups of the components.…”

Section: Introductionmentioning

confidence: 99%

eutXG: A Machine-Learning Model to Understand and Predict the Melting Point of Novel X-Bonded Deep Eutectic Solvents

Ayres,

Bandara,

McMillen

et al. 2024

ACS Sustainable Chem. Eng.

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We present the application of an extreme gradient boosting model (eutXG) to predict the melting point (MP) of deep eutectic solvents (DES). The model is based on XGBoost, a decision tree ensemble based on gradient boosting designed to be highly scalable that enables superior training speed and prediction accuracy. The selected model�trained with molecular fingerprints, molar ratios, and selected chemical descriptors�enabled the prediction of the MPs of DES with an average accuracy of 97.6%, which represents a difference of just ±2.4% with respect to the values reported in the literature. Using SHapley Additive exPlanations (SHAP), further insights into the relative importance of different inputs used to train the machine learning model were identified. Moreover, the generalization ability of the eutXG model was critically assessed by comparing the predicted vs the experimentally determined MP of a series of novel DES based on halogen bonding, developed by mixing tetraalkylammonium triiodide salts (NPe 4 I 3 or NHex 4 I 3 ) with organoiodines, such as 1,2diiodotetrafluorobenzene (o-F 4 DIB), 1,3-diiodotetrafluorobenzene (m-F 4 DIB), or 2,5-diiodothiophene (2,5-DIT), demonstrating its ability to predict the actual melting with a difference of only 2 K. Our results not only reinforce the importance of having (at least some) representative data for the training step to increase the accuracy of the model's predictions but also demonstrate the ability of eutXG to accelerate the development of novel applications for this entirely new class of hydrophobic DES, potentially impacting a wide range of fields from pharmaceuticals to agrochemicals.

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“…It is formed by combining two to three solids or liquids at a specific molar ratio where one component functions as the hydrogen bond acceptor (HBA) and the other as hydrogen bond donor (HBD). The HBA is usually a quaternary ammonium salt whereas the HBD may be a carboxylic acid, sugar, alcohol, vitamin or amino acid [2] . The charge delocalization due to dynamic HBA‐HBD intermolecular hydrogen bond interactions results in a clear, homogenous liquid phase exhibiting lower melting point than its individual HBA and HBD components [3] .…”

Section: Introductionmentioning

confidence: 99%

“…The HBA is usually a quaternary ammonium salt whereas the HBD may be a carboxylic acid, sugar, alcohol, vitamin or amino acid. [2] The charge delocalization due to dynamic HBA-HBD intermolecular hydrogen bond interactions results in a clear, homogenous liquid phase exhibiting lower melting point than its individual HBA and HBD components. [3] As highlighted in previous studies, [4][5] the advantages of DES include biodegradability, tunable physicochemical properties and ease of synthesis.…”

Section: Introductionmentioning

confidence: 99%

Microwave‐Assisted Preparation of an Acidic Deep Eutectic Solvent: Green Analysis, Characterization and Application

Yap,

Wang,

Gan

2024

ChemistrySelect

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Microwave irradiation was postulated to reduce time and energy for deep eutectic solvent (DES) production which is in line with the principle of green chemistry. In this study, the choline chloride (ChCl)‐malic acid (MA) DES was prepared using microwave‐assisted (DES‐Mic) and conventional (DES‐Con) approaches. Microwave was a relatively greener approach as it was rapid (5 min) and consumed 92.8 % energy less than DES‐Con. Moreover, DES‐Mic and DES‐Con exhibited similar physicochemical profiles (pH, solubility, density) and rheological properties. Structural profiling through FTIR analysis suggested hydrogen bond formation between the functional groups of ChCl and MA. The FTIR spectra also did not show structural differences in the DES synthesized using different methods. DES‐Mic and DES‐Con exhibited superior 2,2‐diphenyl‐1‐picrylhydrazyl (DPPH) (80.8±0.1 and 83.2±0.3 %, respectively) free radical scavenging activities than ChCl (15.6±0.8 %), MA (20.0±1.4 %) and ChCl:MA aqueous mixture without subjected to DES synthesis conditions (ChCl:MAaq; 23.3±0.8 %). Both DES were also proven as more efficient solvents for the extraction of polysaccharides from ramie leaf, as they recorded higher yields (21.4±1.9 and 22.2±1.0 %, respectively) than equimolar of MA (17.7±2.6 %) and ChCl (6.4±0.2 %). Overall, microwave was proven as a more sustainable approach for DES preparation compared to conventional method, which could be further improvised for industrial applications.

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Big data for a deep problem: Understanding the formation of NADES through comprehensive chemical analysis and RDKit

Cited by 6 publications

References 72 publications

Natural Deep Eutectic Solvents (NADES): Manufacture, Characteristics, and Their Significance as Designer Solvents

Natural Deep Eutectic Solvents (NADES): Manufacture, Characteristics, and Their Significance as Designer Solvents

eutXG: A Machine-Learning Model to Understand and Predict the Melting Point of Novel X-Bonded Deep Eutectic Solvents

Microwave‐Assisted Preparation of an Acidic Deep Eutectic Solvent: Green Analysis, Characterization and Application

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