Solubility, solution thermodynamics and preferential solvation for 4-bromopyrazole in mixed solvents of (methanol/ethanol  +  water) from  T  =  (283.15 to 318.15)  K

Wang, Shaoling; Du, Cunbin; Zhao, Hongkun

doi:10.1016/j.jct.2017.05.005

Cited by 15 publications

(3 citation statements)

References 38 publications

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“…The solubility of the target compound in different solvents [ 7 , 8 , 9 ] is required for the crystallization process. In addition, solubility data for metoprolol succinate in different solvents is also beneficial for analytical [ 10 ], inclusion [ 11 ], molecular thermodynamic, and interaction studies [ 12 ]. In recent years, physical–chemical properties such as the density, viscosity, and refractive index of aqueous solutions of metoprolol succinate have been studied [ 13 ].…”

Section: Introductionmentioning

confidence: 99%

Measurements, Thermodynamic Modeling, and a Hydrogen Bonding Study on the Solubilities of Metoprolol Succinate in Organic Solvents

Shen

Liang

2018

Molecules

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The solubilities of metoprolol succinate (a cardioselective β1 adrenergic receptor) in methanol, ethanol, n-propanol, isopropanol, n-butanol, ethyl acetate, and acetone were measured at temperatures ranging from (278.2 to 318.2) K using a solid–liquid equilibrium method. The solubility of metoprolol succinate increases with increasing temperature. At a fixed temperature, the solubility decreases in the order methanol > ethanol > n-butanol > n-propanol > isopropanol > acetone > ethyl acetate. The enthalpy of fusion and the melting point of metoprolol succinate were determined by differential scanning calorimetry. The thermodynamic properties of the dissolution process, determined by a van’t Hoff analysis, have been obtained and are discussed. The modified Apelblat equation, Wilson model, and non-random two-liquid (NRTL) model were employed to correlate the solubilities of metoprolol succinate in different solvents. Finally, a quantitative structure–property relationship (QSPR) study of physical properties of solvents and density functional theory simulations of hydrogen-bonding structure were carried out to give the explanation for the sequence of solubility in alcohols. The density functional theory (DFT) calculations well illustrated that the solubility of metoprolol succinate in various alcohols can be mainly attributed to the intra- and intermolecular hydrogen bonds in metoprolol succinate-solvent complexes.

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Section: Introductionmentioning

confidence: 99%

Measurements, Thermodynamic Modeling, and a Hydrogen Bonding Study on the Solubilities of Metoprolol Succinate in Organic Solvents

Shen

Liang

2018

Molecules

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“…Finally, it is noteworthy that in our previous studies [63][64][65], the solute is preferentially solvated by co-solvent in co-solventrich mixtures. However, ribavirin (II) is preferentially solvated by water in this region.…”

Section: Preferential Solvation Of Ribavirinmentioning

confidence: 74%

Thermodynamic modelling of solubility and preferential solvation for ribavirin (II) in co-solvent mixtures of (methanol, n -propanol, acetonitrile or 1,4-dioxane) + water

Cong

et al. 2017

The Journal of Chemical Thermodynamics

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a b s t r a c tThe equilibrium solubility of ribavirin in solvent mixtures of {methanol (1) + water (2)}, {n-propanol (1) + water (2)}, {acetonitrile (1) + water (2)} and {1,4-dioxane (1) + water (2)} was determined experimentally by using isothermal dissolution equilibrium method within the temperature range from (278.15 to 318.15) K under atmospheric pressure (101.1 kPa). At the same temperature and mass fraction of methanol (n-propanol, acetonitrile or 1,4-dioxane), the mole fraction solubility of ribavirin is greater in (methanol + water) than in the other three solvent mixtures. The preferential solvation parameters were derived from their thermodynamic solution properties by means of the inverse Kirkwood-Buff integrals. The preferential solvation parameters for methanol, n-propanol, acetonitrile or 1,4-dioxane (dx 1,3 ) were negative in the four solvent mixtures with a very wide compositions, which indicated that ribavirin was preferentially solvated by water. Temperature had little effect on the preferential solvation magnitudes. The higher solvation by water could be explained in terms of the higher acidic behaviour of water interacting with the Lewis basic groups of the ribavirin. Besides, the solubility of the drugs was mathematically represented by using the Jouyban-Acree model, van't Hoff-Jouyban-Acree model and Apelblat-Jouyban-Acree model obtaining average relative deviations lower than 1.57% for correlative studies. It is noteworthy that the solubility data presented in this work contribute to expansion of the physicochemical information about the solubility of drugs in binary solvent mixtures and also allows the thermodynamic analysis of the respective dissolution and specific solvation process.

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“…The Jouyban–Acree model usually provides mathematic descriptions for the solubility dependence on both temperature and solvent composition for binary solvents. − The model is described in eq : In the above formula, x 3 represents the mole fraction solubility of 2-chloro-3-(trifluoromethyl)pyridine in the binary solvent mixtures, x 1 and x 2 represent the mole fraction solubility of 2-chloro-3-(trifluoromethyl)pyridine in pure solvent, ω 1 and ω 2 mean the mass fractions of solvent in binary solvent, respectively, and J i represents parameter of the Jouyban–Acree model.…”

Section: Results and Discussionmentioning

confidence: 99%

Solubility Behavior of 2-Chloro-3- (trifluoromethyl)pyridine in (Ethyl Acetate + n-Butanol, DMF + n-Butanol, DMF + Ethanol) Solvent Mixtures

Zhao

Zhang

2019

J. Chem. Eng. Data

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The solubility of 2-chloro-3-(trifluoromethyl)pyridine in ethyl acetate + n-butanol, DMF + n-butanol, and DMF + ethanol solvent mixtures was determined via an isothermal static method within the temperature scope of 263.15–303.15 K under 101.3 KPa. The solubility of 2-chloro-3-(trifluoromethyl)pyridine increased with increasing temperature and mass fraction of ethyl acetate or DMF in the binary solvent systems. The modified Apelblat model, Jouyban–Acree model, and Sun model were used to correlate the solubility data of 2-chloro-3-(trifluoromethyl)pyridine in the binary mixtures. The values of RD and RMSD indicated that three models fit the solubility data quite well, and the Sun model gave the best correlation of the solubility data in the binary ethyl acetate + n-butanol and DMF + n-butanol solvents. The Apelblat model gave the best correlation of the solubility data in the binary DMF + ethanol solvent.

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Solubility, solution thermodynamics and preferential solvation for 4-bromopyrazole in mixed solvents of (methanol/ethanol + water) from T = (283.15 to 318.15) K

Cited by 15 publications

References 38 publications

Measurements, Thermodynamic Modeling, and a Hydrogen Bonding Study on the Solubilities of Metoprolol Succinate in Organic Solvents

Measurements, Thermodynamic Modeling, and a Hydrogen Bonding Study on the Solubilities of Metoprolol Succinate in Organic Solvents

Thermodynamic modelling of solubility and preferential solvation for ribavirin (II) in co-solvent mixtures of (methanol, n -propanol, acetonitrile or 1,4-dioxane) + water

Solubility Behavior of 2-Chloro-3- (trifluoromethyl)pyridine in (Ethyl Acetate + n-Butanol, DMF + n-Butanol, DMF + Ethanol) Solvent Mixtures

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