Abraham model correlations for describing solute transfer into ionic liquid solvents: calculation of ion-specific equation coefficients for the 4,5-dicyano-2-(trifluoromethyl)imidazolide anion

Stephens, Timothy W.; Hart, Erin; Kuprasertkul, Nina; Mehta, Sumedha; Wadawadigi, Akash; Acree, William E.; Abraham, Michael H.

doi:10.1080/00319104.2014.929949

Cited by 25 publications

(6 citation statements)

References 29 publications

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“…A detailed list of all the contributions to ion-specific LSER covering years from 2010 to 2013 can be found in the references list of the paper of Stephens et al, who in 2014 provided a comprehensive revision and extension of the model. In this version of the ion-specific LSER, the parameters table covered 40 different cations and 16 different anions, so that the number of binary ILs that can be tested by the model (40 × 16 = 640) increased approximately by a factor of 9 compared to the pioneering papers of Sprunger et al. − Since the publication of the paper of Stephens et al., the range of applications of the model has additionally increased as the parameters for several novel cationic and anionic structures (like imidazolide anions or quinuclidinium-based cations) have been calculated and reported. − …”

Section: Introductionmentioning

confidence: 99%

In Silico Calculation of Infinite Dilution Activity Coefficients of Molecular Solutes in Ionic Liquids: Critical Review of Current Methods and New Models Based on Three Machine Learning Algorithms

Paduszyński

2016

J. Chem. Inf. Model.

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The aim of the paper is to address all the disadvantages of currently available models for calculating infinite dilution activity coefficients (γ(∞)) of molecular solutes in ionic liquids (ILs)-a relevant property from the point of view of many applications of ILs, particularly in separations. Three new models are proposed, each of them based on distinct machine learning algorithm: stepwise multiple linear regression (SWMLR), feed-forward artificial neural network (FFANN), and least-squares support vector machine (LSSVM). The models were established based on the most comprehensive γ(∞) data bank reported so far (>34 000 data points for 188 ILs and 128 solutes). Following the paper published previously [J. Chem. Inf. Model 2014, 54, 1311-1324], the ILs were treated in terms of group contributions, whereas the Abraham solvation parameters were used to quantify an impact of solute structure. Temperature is also included in the input data of the models so that they can be utilized to obtain temperature-dependent data and thus related thermodynamic functions. Both internal and external validation techniques were applied to assess the statistical significance and explanatory power of the final correlations. A comparative study of the overall performance of the investigated SWMLR/FFANN/LSSVM approaches is presented in terms of root-mean-square error and average absolute relative deviation between calculated and experimental γ(∞), evaluated for different families of ILs and solutes, as well as between calculated and experimental infinite dilution selectivity for separation problems benzene from n-hexane and thiophene from n-heptane. LSSVM is shown to be a method with the lowest values of both training and generalization errors. It is finally demonstrated that the established models exhibit an improved accuracy compared to the state-of-the-art model, namely, temperature-dependent group contribution linear solvation energy relationship, published in 2011 [J. Chem. Eng. Data 2011, 56, 3598-3606].

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Section: Introductionmentioning

confidence: 99%

In Silico Calculation of Infinite Dilution Activity Coefficients of Molecular Solutes in Ionic Liquids: Critical Review of Current Methods and New Models Based on Three Machine Learning Algorithms

Paduszyński

2016

J. Chem. Inf. Model.

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“…Thus, the calculated coefficients in Equations (14) and (15) represent the cation-specific Abraham model equation coefficients for [BM 2 Im] + , while the calculated coefficients in Equations (16) and (17) correspond to the cation-specific equation coefficients for [4-CNBPy] + . The newly calculated cation-specific equation coefficients can be combined with our existing 17 anion-specific equation coefficients [61,66] to enable one to predict log K and log P values for solutes dissolved in an additional 34 IL solvents.…”

Section: Resultsmentioning

confidence: 99%

“…Abraham model correlations have been reported for well over 100 total different tradition organic solvents [29][30][31][32][33][34][35][36][37][38][39][40][41][42][43][44][45][46] and IL organic solvents, [47][48][49][50][51][52][53][54][55][56][57][58][59][60][61] as well as for binary aqueous-ethanol [62] mixtures. Our focus in the present study is IL solvents.…”

Section: Introductionmentioning

confidence: 99%

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Abraham model ion-specific equation coefficients for the 1-butyl-2,3-dimethyimidazolium and 4-cyano-1-butylpyridinium cations calculated from measured gas-to-liquid partition coefficient data

Jiang

Cheeran

et al. 2016

Physics and Chemistry of Liquids

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2016): Abraham model ion-specific equation coefficients for the 1-butyl-2,3-dimethyimidazolium and 4-cyano-1-butylpyridinium cations calculated from measured gas-to-liquid partition coefficient data, Physics and Chemistry of Liquids, ABSTRACT Partition coefficient and gas solubility data have been assembled from the published chemical and engineering literature for solutes dissolved in anhydrous 1-butyl-3-methylimidazolium dicyanamide, 1-butyl-2,3-dimethylimidazolium bis(trifluoromethylsulfonyl)imide, and 4-cyano-1-butylpyrridinium bis(trifluoromethylsulfonyl)imide. More than 60 experimental data points were gathered for each IL solvent. The compiled experimental data were used to derive Abraham model correlations for describing the solute transfer properties into the three anhydrous IL solvents from both the gas phase and water. The derived mathematical correlations described the observed solute transfer properties, expressed as the logarithm of the water-to-IL partition coefficient and logarithm of the gas-to-IL solvent partition coefficient, to within standard deviations of 0.125 log units (or less). Abraham model ion-specific equation coefficients are also calculated for the 1-butyl-2,3-dimethylimidazolium and 4-cyano-1-butylpyridinium cations. ARTICLE HISTORY

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“…3−8 Equation coefficients are available for partition from water and the gas phase into ionic liquids, 16,17 and solubilities in these ionic liquids can then easily be calculated. Coefficients are also available for equations related to various biological and environmental processes, 18−20 and it is a matter of simple arithmetic to obtain values for these processes.…”

Section: Resultsmentioning

confidence: 99%

Deduction of Physicochemical Properties from Solubilities: 2,4-Dihydroxybenzophenone, Biotin, and Caprolactam as Examples

et al. 2015

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Solubilities of 2,4-dihydroxybenzophenone have been measured at 298 K in 19 organic solvents. Combination with a known value of the solubility in water enables corresponding partition coefficients from water to these solvents to be deduced. It is shown that solubilities, via the partition coefficients, can yield the Abraham descriptors for 2,4-dihydroxybenzophenone, and that these, in turn, can be used to estimate a very large number of further solubilities, partition coefficients, and values of biological and environmental properties. This method of extracting information from solubilities is further illustrated using literature data on solubilities of biotin and of caprolactam.

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Abraham model correlations for describing solute transfer into ionic liquid solvents: calculation of ion-specific equation coefficients for the 4,5-dicyano-2-(trifluoromethyl)imidazolide anion

Cited by 25 publications

References 29 publications

In Silico Calculation of Infinite Dilution Activity Coefficients of Molecular Solutes in Ionic Liquids: Critical Review of Current Methods and New Models Based on Three Machine Learning Algorithms

In Silico Calculation of Infinite Dilution Activity Coefficients of Molecular Solutes in Ionic Liquids: Critical Review of Current Methods and New Models Based on Three Machine Learning Algorithms

Abraham model ion-specific equation coefficients for the 1-butyl-2,3-dimethyimidazolium and 4-cyano-1-butylpyridinium cations calculated from measured gas-to-liquid partition coefficient data

Deduction of Physicochemical Properties from Solubilities: 2,4-Dihydroxybenzophenone, Biotin, and Caprolactam as Examples

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