Development of Abraham model correlations for dimethyl adipate from measured solubility data of nonelectrolyte organic compounds

Shanmugam, Nikita; Zhou, Amy; Motati, Ramya; Yao, Emily; Kandi, Trisha; Longacre, Laine; Benavides, Darla; Motati, Saikiran; Acree, William E.

doi:10.1080/00319104.2023.2225206

Cited by 10 publications

(1 citation statement)

References 56 publications

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“…For example, the estimated values for isopropyl acetate (Ê T (30) = 0.319), pentyl acetate (Ê T (30) = 0.290), tert-butyl acetate (Ê T (30) = 0.315), and isopropyl myristate (Ê T (30) = 0.322) are comparable to experimental values for other monoester solvents such as methyl acetate (Ê T (30) = 0.247), ethyl acetate (Ê T (30) = 0.225), propyl acetate (Ê T (30) = 0.210), and butyl acetate (Ê T (30) = 0.241). The slightly larger estimated value of Ê T (30) = 0.361 for dimethyl adipate likely arises because of the additional ester functional group [40]. By employing SMILES enumeration [38], we achieved significant improvements in model performance, as evidenced by the test-set statistics calculated on the same dataset as before.…”

Section: Predicting Et-values Using Standard Abraham Solvent Parametersmentioning

confidence: 75%

Reichardt’s Dye-Based Solvent Polarity and Abraham Solvent Parameters: Examining Correlations and Predictive Modeling

Acree

Lang

2023

Liquids

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The concept of “solvent polarity” is widely used to explain the effects of using different solvents in various scientific applications. However, a consensus regarding its definition and quantitative measure is still lacking, hindering progress in solvent-based research. This study hopes to add to the conversation by presenting the development of two linear regression models for solvent polarity, based on Reichardt’s ET(30) solvent polarity scale, using Abraham solvent parameters and a transformer-based model for predicting solvent polarity directly from molecular structure. The first linear model incorporates the standard Abraham solvent descriptors s, a, b, and the extended model ionic descriptors j+ and j−, achieving impressive test-set statistics of R2 = 0.940 (coefficient of determination), MAE = 0.037 (mean absolute error), and RMSE = 0.050 (Root-Mean-Square Error). The second model, covering a more extensive chemical space but only using the descriptors s, a, and b, achieves test-set statistics of R2 = 0.842, MAE = 0.085, and RMSE = 0.104. The transformer-based model, applicable to any solvent with an associated SMILES string, achieves test-set statistics of R2 = 0.824, MAE = 0.066, and RMSE = 0.095. Our findings highlight the significance of Abraham solvent parameters, especially the dipolarity/polarizability, hydrogen-bond acidity/basicity, and ionic descriptors, in predicting solvent polarity. These models offer valuable insights for researchers interested in Reichardt’s ET(30) solvent polarity parameter and solvent polarity in general.

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Section: Predicting Et-values Using Standard Abraham Solvent Parametersmentioning

confidence: 75%

Reichardt’s Dye-Based Solvent Polarity and Abraham Solvent Parameters: Examining Correlations and Predictive Modeling

Acree

Lang

2023

Liquids

Self Cite

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Analysis of agomelatine (Form Ⅱ) dissolution behavior in different mono-solvents: Solubility, solvation thermodynamics as well as inter-molecular interactions

Ma,

Wu,

et al. 2024

The Journal of Chemical Thermodynamics

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Updated Abraham model correlations for describing solute transfer into both 2-Pentanol and 3-Methyl-1-butanol based on much larger data sets

Kandi,

Motati,

Motati

et al. 2023

Physics and Chemistry of Liquids

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Development of Abraham model correlations for dimethyl adipate from measured solubility data of nonelectrolyte organic compounds

Cited by 10 publications

References 56 publications

Reichardt’s Dye-Based Solvent Polarity and Abraham Solvent Parameters: Examining Correlations and Predictive Modeling

Reichardt’s Dye-Based Solvent Polarity and Abraham Solvent Parameters: Examining Correlations and Predictive Modeling

Analysis of agomelatine (Form Ⅱ) dissolution behavior in different mono-solvents: Solubility, solvation thermodynamics as well as inter-molecular interactions

Updated Abraham model correlations for describing solute transfer into both 2-Pentanol and 3-Methyl-1-butanol based on much larger data sets

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