Enthalpy of solvation correlations for organic solutes and gases dissolved in dichloromethane and 1,4-dioxane

Wilson, Anastasia; Tian, Amy; Dabadge, Nishu; Acree, William E.; Varfolomeev, Mikhail A.; Rakipov, Ilnaz T.; Arkhipova, Svetlana M.; Abraham, Michael H.

doi:10.1007/s11224-013-0233-1

Cited by 28 publications

(8 citation statements)

References 85 publications

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“…The Abraham model was developed and is widely used to predict partition coefficients for both conventional organic solvents [ 1 - 11 ] and ionic liquid solvents [ 12 , 13 ], for the partitioning of drug molecules between blood and select body organs [ 14 - 18 ], and for partitioning into micelles [ 19 ] and for prediction of enthalpies of solvation in organic solvents [ 20 ] and ionic organic liquids [ 21 ]. The Abraham model is based on the linear free energy relationship (LFER) where logP is the solvent/water partition coefficient.…”

Section: Introductionmentioning

confidence: 99%

Predicting Abraham model solvent coefficients

Bradley

Abraham

Acree

et al. 2015

Chemistry Central Journal

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BackgroundThe Abraham general solvation model can be used in a broad set of scenarios involving partitioning and solubility, yet is limited to a set of solvents with measured Abraham coefficients. Here we extend the range of applicability of Abraham’s model by creating open models that can be used to predict the solvent coefficients for all organic solvents.ResultsWe created open random forest models for the solvent coefficients e, s, a, b, and v that had out-of-bag R2 values of 0.31, 0.77, 0.92, 0.47, and 0.63 respectively. The models were used to suggest sustainable solvent replacements for commonly used solvents. For example, our models predict that propylene glycol may be used as a general sustainable solvent replacement for methanol.ConclusionThe solvent coefficient models extend the range of applicability of the Abraham general solvation equations to all organic solvents. The models were developed under Open Notebook Science conditions which makes them open, reproducible, and as useful as possible.Graphical AbstractChemical space for solvents with known Abraham coefficients.Electronic supplementary materialThe online version of this article (doi:10.1186/s13065-015-0085-4) contains supplementary material, which is available to authorized users.

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Section: Introductionmentioning

confidence: 99%

Predicting Abraham model solvent coefficients

Bradley

Abraham

Acree

et al. 2015

Chemistry Central Journal

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“…This study continues our combined experimental and theoretical examination of gas-toorganic solvent transfer processes for nonelectrolyte solutes [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19]. Such processes govern chemical separations by gas-liquid chromatography, measurement of solubilities and activity coefficients by inert-gas stripping methods, and the removal and pre-concentration of volatile organic solutes from aqueous analytical samples using headspace single drop micro-extraction methods.…”

Section: Introductionmentioning

confidence: 89%

“…In previous publications [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15] we have developed Abraham model correlations:…”

Section: Introductionmentioning

confidence: 99%

“…The organic solvents included several saturated hydrocarbons [1,2] and aromatic hydrocarbons [1,3,4], chlorinated alkanes [4][5][6], several primary, secondary and tertiary alcohols [7][8][9][10][11], two dialkyl carbonates [12], one alkyl acetate solvent [13], one dialkyl ether [13] and two cyclic ethers [6,8], as well as several miscellaneous organic solvents [9,14,15]. In each case eqns.…”

Section: Introductionmentioning

confidence: 99%

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Effect of halogen substitution on the enthalpies of solvation and hydrogen bonding of organic solutes in chlorobenzene and 1,2-dichlorobenzene derived using multi-parameter correlations

et al. 2015

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Enthalpies of solution at infinite dilution at 298 K, ΔsolnH A/Solvent , have been measured by isothermal solution calorimetry for 43 and 72 organic solutes dissolved in chlorobenzene and 1,2-dichlorobenzene, respectively. The measured ΔsolnH A/Solvent data, along with published ΔsolnH A/Solvent values taken from the published literature for solutes dissolved in both chlorobenzene solvents, were converted to enthalpies of solvation, ΔsolvH A/Solvent , using standard thermodynamic equations. Abraham model correlations were developed from the experimental ΔsolvH A/Solvent data. The best derived correlations describe the experimental gas-to-chlorobenzene and gas-to-1,2-dichlorobenzene enthalpies of solvation to within standard deviations of 1.5 kJ mol -1 and 1.9 kJ mol -1 , respectively. Enthalpies of X-H…π (X -O, N, and C) hydrogen bond formation of proton donor solutes (alcohols, amines, chlorinated hydrocarbons and etc.) with chlorobenzene and 1,2-dichlorobenzene were calculated based on the Abraham solvation equation. Obtained values are in good agreement with the results determined using conventional methods.

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“…Wilson et al [131] used solution calorimetry to determine the enthalpies of solvation of organic solutes in dichloromethane and 1,4-dioxane with the aim of analyzing correlations between enthalpies of solvation for organic solutes and gases in dichloromethane and 1,4-dioxane. 1,3-Dioxane has been a much less popular solvent than its 1,4-isomer.…”

Section: Issuementioning

confidence: 99%