Equilibrium solubility, Hansen solubility parameter, dissolution thermodynamics, transfer property and preferential solvation of zonisamide in aqueous binary mixtures of ethanol, acetonitrile, isopropanol and N,N-dimethylformamide

Zhang, Cunliang; Jouyban, Abolghasem; Zhao, Hongkun; Farajtabar, Ali; Acree, William E.

doi:10.1016/j.molliq.2020.115219

Cited by 44 publications

(41 citation statements)

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“…The mutual miscibility of solute and solvent molecules is evaluated by means of the Hansen solubility parameter (HSP). − The total Hildebrand solubility parameter (δ t ) can be divided into the hydrogen-bonded solubility parameter (δ h ), polar solubility parameter (δ p ), and dispersion solubility parameter (δ d ) by …”

Section: Theory Considerationmentioning

confidence: 99%

“…The values of three-dimensional solubility parameters δ d , δ p , and δ h of monosolvents employed in the present contribution are reachable from the literature . The total and partial Hansen solubility parameters for 3,3′-diaminodiphenyl sulfone can be estimated by the use of the method of group contribution put forward by Hoftyzer and van Krevelen: , wherein E hi , F pi , and F di represent the contribution to hydrogen bonding energy, polar force, and dispersion force for group i of the 3,3′-diaminodiphenyl sulfone molecule, respectively, in which the addition properties of molar attraction forces are considered.…”

Section: Theory Considerationmentioning

confidence: 99%

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Solubility, Three-Dimensional Hansen Solubility Parameters, and Solution Thermodynamics of 3,3′-Diaminodiphenyl Sulfone in 14 Neat Solvents from 283.15 to 328.15 K

et al. 2021

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By means of the saturation shake-flask technique, the saturation solubility data of 3,3′-diaminodiphenyl sulfone in 14 monosolvents (n-propanol, N,N-dimethylformamide, methanol, ethanol, ethylene glycol, cyclohexane, acetonitrile, isopropanol, water, n-butanol, ethyl acetate, 1,4-dioxane, isobutanol, and 1-heptanol) was achieved at temperatures from 283.15 to 328.15 K and ambient pressure (p = 101.2 kPa). No phenomenon of crystalline form transformation or solvation occurred after dissolution of 3,3′-diaminodiphenyl sulfone in different solvents. The solubility values (mole fraction) of 3,3′-diaminodiphenyl sulfone in above 14 solvents increased as the temperature elevated and obeyed the decreasing tendency in different monosolvents as follows: N,N-dimethylformamide > ethyl acetate > acetonitrile > ethylene glycol > 1,4-dioxane > methanol > ethanol > isobutanol > n-propanol > n-butanol > isopropanol > 1-heptanol > water > cyclohexane. The mutual miscibility of solvent and 3,3′-diaminodiphenyl sulfone was explained through the three-dimensional Hansen solubility parameter. Examination was carried out for molecular interactions between the solute–solvent and solvent–solvent species by means of the linear solvation energy relationships. The solubility data obtained through experiments was correlated by the use of four models/equations, namely, the NRTL model, Apelblat equation, λh equation, and Wilson model. Correlation resulted in the maximum root-mean-square and relative average deviation values of, respectively, 397.1 × 10–5 and 7.57 × 10–2. The Apelblat equation gave lower relative average deviations than the other models/equations for a certain neat solvent. Also, the mixing thermodynamic properties, infinite-dilution activity coefficient, and reduced excess enthalpy were obtained in terms of the Wilson model.

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Section: Theory Considerationmentioning

confidence: 99%

Section: Theory Considerationmentioning

confidence: 99%

Solubility, Three-Dimensional Hansen Solubility Parameters, and Solution Thermodynamics of 3,3′-Diaminodiphenyl Sulfone in 14 Neat Solvents from 283.15 to 328.15 K

et al. 2021

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“…Preferential solvation may give rise to the difference between the bulk solvent composition and shell solvent composition nearby the solute, rather than a particular atom of the solute. The inverse Kirkwood−Buff integrals (abbreviated as IKBIs, eq 21) defines the local compositions of a specific solvent nearby the solute compared with the overall solution compositions: [6][7][8][9][10][11][12]27,41,42…”

Section: ■ Theorymentioning

confidence: 99%

“…where r refers to the distance between the centers of solute The preferential solvation parameter, δx 1,3 , of 1-(2bromophenyl)-pyrrole-2,5-dione (3) by isopropanol, ethanol, NMP, or methanol (1) in aqueous solutions can be described as [6][7][8][9][10][11][12]27,41,42 x x x x…”

Section: ■ Theorymentioning

confidence: 99%

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Solubility Determination, Modeling, and Preferential Solvation of 1-(2-Bromophenyl)-pyrrole-2,5-dione in Aqueous Binary Mixtures of Isopropanol, Ethanol, N-Methyl-2-pyrrolidinone and Methanol

Gao

et al. 2021

J. Chem. Eng. Data

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Experimental determination of equilibrium solubility of 1-(2-bromophenyl)-pyrrole-2,5-dione in binary aqueous solutions containing a co-solvent of isopropanol, ethanol, N-methyl-2-pyrrolidinone (NMP) or methanol over temperatures from 278.15 to 323.15 K was made by the shake-flask technique under local pressure of 101.2 kPa. At the identical experimental conditions (temperature and mass fraction compositions of co-solvents), the maximum equilibrium solubility magnitude in a mole fraction of 1-(2-bromophenyl)-pyrrole-2,5-dione was recorded in the NMP (1) + water (2) system; and the minimum one, in the isopropanol (1) + water (2) system. The solvent effect was quantitatively analyzed by employing the KAT-LSER model, representing the solubility parameter and dipolarity–polarizability had main contributions to the solubility variation at 298.15 K. Four relationships, such as the Jouyban–Acree model, modified Wilson model, Jouyban–Acree–van’t Hoff model, and mixture response surface (MRS) model, were employed to correlate the determined solubility magnitudes, attaining the root-mean-square deviations of no higher than 493.0 × 10–5 and relative average deviations of no higher than 5.59%. The molecule interactions of solute–solvent and solvent–solvent were investigated through the extended Hildebrand solubility approach. In water-rich composition regions, there was some association between 1-(2-bromophenyl)-pyrrole-2,5-dione and solution. Furthermore, the local mole fractions of isopropanol (ethanol, NMP, or methanol) and water nearby 1-(2-bromophenyl)-pyrrole-2,5-dione were quantitatively evaluated by the inverse Kirkwood–Buff integrals. 1-(2-Bromophenyl)-pyrrole-2,5-dione was preferentially solvated by water in water-rich proportions; while in co-solvent-rich proportions for the solutions studied, it was preferentially solvated by isopropanol (ethanol, NMP, or methanol). In water-rich ranges, 1-(2-bromophenyl)-pyrrole-2,5-dione could be predominantly serving as a Lewis base in front of water molecules.

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Simulation of Clozapine Solubility in Mono- and Mixed Solvents at Different Temperatures

Rahimpour

Zhao

et al. 2022

J Solution Chem

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Equilibrium solubility, Hansen solubility parameter, dissolution thermodynamics, transfer property and preferential solvation of zonisamide in aqueous binary mixtures of ethanol, acetonitrile, isopropanol and N,N-dimethylformamide

Cited by 44 publications

References 46 publications

Solubility, Three-Dimensional Hansen Solubility Parameters, and Solution Thermodynamics of 3,3′-Diaminodiphenyl Sulfone in 14 Neat Solvents from 283.15 to 328.15 K

Solubility, Three-Dimensional Hansen Solubility Parameters, and Solution Thermodynamics of 3,3′-Diaminodiphenyl Sulfone in 14 Neat Solvents from 283.15 to 328.15 K

Solubility Determination, Modeling, and Preferential Solvation of 1-(2-Bromophenyl)-pyrrole-2,5-dione in Aqueous Binary Mixtures of Isopropanol, Ethanol, N-Methyl-2-pyrrolidinone and Methanol

Simulation of Clozapine Solubility in Mono- and Mixed Solvents at Different Temperatures

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