Solubility of crystalline nonelectrolyte solutes in organic solvents: mathematical correlation of 4-chloro-3-nitrobenzoic acid and 2-chloro-5-nitrobenzoic acid solubilities with the Abraham solvation parameter model

Stovall, Dawn M.; Givens, Chelsea; Keown, S. R.; Hoover, Kaci R.; Barnes, Robin; Harris, C. W.; Lozano, José Manuel; Nguyen, Minh Tho; Rodriguez, Erick; Acree, William E.; Abraham, Michael H.

doi:10.1080/00319100500111293

Cited by 66 publications

(21 citation statements)

References 26 publications

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“…The concentration of each diluted solution was calculated from a BeerLambert law absorbance versus concentration curve generated from the measured absorbances of nine carefully prepared standard solutions of known solute concentration. The analysis wavelengths and concentration ranges used for each solute have been reported in our earlier publications [62][63][64][65][66][67][68][69][70][71][72][73][74][75][76][77][78][79]. Molar concentrations were converted into mole fraction solubilities using the mass of the sample analyzed, molar masse of 2-butoxyethanol and the respective solutes, volume of the volumetric flasks, and any dilutions needed to get the measured absorbances on the Beer-Lambert law curve.…”

Section: Solubility Measurementsmentioning

confidence: 99%

Abraham model correlations for describing solute transfer into 2-butoxyethanol from both water and the gas phase at 298K

Sedov

Stolov

Hart

et al. 2015

Journal of Molecular Liquids

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Infinite dilution activity coefficients (γ∞) were measured at 298 K for 12 different aliphatic hydrocarbons (alkanes, cycloalkanes, alkenes), 11 different aromatic compounds (benzene, alkylbenzenes, halobenzenes, naphthalene), and 2-chloro-2-methylpropane dissolved in 2-butoxyethanol at 298 K using a headspace gas chromatographic method. As part of the experimental study solubilities of 19 crystalline nonelectrolyte solutes (2-hydroxybenzoic acid, acetylsalicylic acid, 3,5-dinitro-2-methylbenzoic acid, acenaphthene, trans-stilbene, xanthene, phenothiazine, 3,5-dinitrobenzoic acid, 3-chlorobenzoic acid, 2-methylbenzoic acid, 4-chloro-3-nitrobenzoic acid, 2-chloro-5-nitrobenzoic acid, benzoic acid, 4-aminobenzoic acid, benzil, thioxanthen-9-one, 3-nitrobenzoic acid, fluoranthene, and diphenyl sulfone) were determined in 2-butoxyethanol at 298 K using a static, spectrophotometric method. The experimental values 2 were converted to gas-to-2-butoxyethanol, water-to-2-butoxyethanol partition coefficients, and molar solubility ratios using standard thermodynamic relationships. Abraham model correlations for solute transfer into 2-butoxyethanol were derived from the calculated partition coefficients and solubility ratios. The derived Abraham model describes the observed partition coefficient and solubility data to within 0.14 log units (or less).

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Section: Solubility Measurementsmentioning

confidence: 99%

Abraham model correlations for describing solute transfer into 2-butoxyethanol from both water and the gas phase at 298K

Sedov

Stolov

Hart

et al. 2015

Journal of Molecular Liquids

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“…solvent's coefficients), which depend upon the solvent system under consideration. Numerical values of the model constants have been reported in the literature [3][4] for several water-to-organic solvent and gas-to-organic solvent systems.…”

Section: Introductionmentioning

confidence: 99%

“…3, 2008 Abraham models employ five parameters for each solute and six solvent coefficients that were computed for a number of common solvents. [3][4] The basic models proposed for process within condensed phases is: (1) and for process involving gas-to-condensed phase transfer is: (2) where C S and C W are the solute solubility in the organic solvent and water (in mole per liter), respectively, C G is the gas phase concentration of the solute, E is the excess molar refraction, S is dipolarity/polarizability of solute, A denotes the solute's hydrogen-bond acidity, B stands for the solute's hydrogen-bond basicity, V is the McGowan volume of the solute, and L is the logarithm of the solute gas-hexadecane partition coefficient at 298.15 K. In equations (1) and (2) the coefficients c, e, s, a, b, v and l are the model constants (i.e. solvent's coefficients), which depend upon the solvent system under consideration.…”

Section: Introductionmentioning

confidence: 99%

“…The QSPR models proposed in an earlier work using water-to-solvent coefficients were: (4) (5) (6) and the QSPR models using gas-to-solvent coefficients were: (7) (8) (9) The applicability of the proposed method was checked using 194 solubility data sets of five different solutes in various non-aqueous binary solvents. In this work, the possibility of replacing experimentally obtained Abraham parameters with the computed parameters is examined.…”

Section: Introductionmentioning

confidence: 99%

“…The Abraham solvation parameter models provided numerical methods for prediction of solutes' solubility in a wide variety of neat organic solvents. [1][2][3][4][5][6] The Vol. 19, No.…”

Section: Introductionmentioning

confidence: 99%

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Solubility prediction of solutes in non-aqueous binary solvent mixtures

Jouyban¹,

Khoubnasabjafari²,

Soltani³

et al. 2008

J. Braz. Chem. Soc.

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Foi investigada a possibilidade de substituir os parâmetros de Abraham calculados teoricamente pelos parâmetros experimentais, na previsão da solubilidade de solutos não-aquoso em misturas de solventes binários, utilizando-se o modelo de Jouyban-Acree. As solubilidades de 90 conjuntos de dados, coletados a partir da literatura, foram preditas utilizando-se estes parâmetros, os coeficientes de solventes e também as solubilidades de sistemas mono-solventes. A precisão das solubilidades previstas foi avaliada calculando-se a média percentual do desvio (MPD) e também dos desvios percentuais (IPDs) individuais. O MPD global para a análise utilizando os parâmetros de Abraham, experimentais e teóricos, foram os mesmos e <14%. Uma boa distribuição (IPD) foi obtida por estas análises numéricas. Os conjuntos de dados investigados neste trabalho foram coletados a várias temperaturas e os resultados confirmaram a possibilidade de previsão da solubilidade em solventes binários a diferentes temperaturas. Explorou-se a possibilidade de cálculos ab initio nesta previsão utilizando as solubilidades calculadas em sistemas mono-solventes. No entanto, a diferença entre os valores previstos e observados, para os coeficientes dos solventes, aumentou para aproximadamente 60% e 200% quando usou-se gás e água, respectivamente. Estes, são valores muito grandes para várias aplicações de previsão.The possibility of replacing theoretically computed Abraham parameters with the experimental Abraham parameters in solubility prediction of solutes in non-aqueous binary solvent mixtures using the Jouyban-Acree model was investigated. The solubilities of 90 data sets collected from the literature were predicted using their Abraham parameters, the solvent coefficients and also the solubilities in mono-solvent systems. The accuracy of the predicted solubilities was evaluated by calculating the mean percentage deviation (MPD) and also individual percentage deviations (IPDs). The overall MPD for the analysis using experimental and computed Abraham parameters were the same and was < 14%. A favoured IPD distribution was obtained for these numerical analyses. The data sets investigated in this work were collected at various temperatures and the results confirmed the possibility of solubility prediction in binary solvents at various temperatures. We did explore the possibility of ab initio solubility prediction of solutes in binary mixtures using the calculated solubilities in mono-solvent systems, however, the difference between the predicted and observed values increased to ca. 60% for gas-to-solvent coefficients and ca. 200% for waterto-solvent coefficients, which is too large for many predictive applications.Keywords: solubility, prediction, non-aqueous mixed solvents, Abraham model, JouybanAcree model IntroductionSolubility of a solute is affected by solvent's and solute's chemical structures and could be mathematically represented using meaningful parameters like Abraham solvation parameters. The Abraham solvation parameter models provided numerical...

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