Effects of intermolecular interactions and solvent properties on the solid-liquid phase equilibrium of isosorbide 5-mononitrate

Cao, Yuechao; Zhang, Junli; Wan, Xuxing; Jia, Shengzhe; Zhang, Guimin; Zhou, Zongyi; Wu, Songgu

doi:10.1016/j.molliq.2022.119974

Cited by 5 publications

(5 citation statements)

References 33 publications

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“…For instance, 1.0 mL of Tol dissolves up to 2.2 mg of PPTCN, whereas 1.0 mg of PTTCN could not be dissolved in 100 mL of Mcy. This observation suggests that the intermolecular interaction between Tol and PTTCN is stronger compared to that between Mcy and PTTCN . To gain insight into this significant difference in solubility, we also performed calculations on the electrostatic potential of PTTCN and compared it with those of Tol and Mcy.…”

Section: Results and Discussionmentioning

confidence: 99%

“…This observation suggests that the intermolecular interaction between Tol and PTTCN is stronger compared to that between Mcy and PTTCN. 44 To gain insight into this significant difference in solubility, we also performed calculations on the electrostatic potential of PTTCN and compared it with those of Tol and Mcy. As depicted in Figure 1c, three cyano groups exhibit substantial negative charge distributions, with the ESP reaching values exceeding −32.0 kcal/mol at the N atom of the cyano units (Table S3).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Luminescent Porous Organic Crystals for Adsorptive Separation of Toluene and Methylcyclohexane

Hu,

Zhao,

Liang

et al. 2024

ACS Appl. Mater. Interfaces

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A butterfly-shaped phenothiazine derivative, PTTCN, was synthesized to obtain pure organic porous crystals for the highly efficient absorptive separation of toluene (Tol) and methylcyclohexane (Mcy). Due to the presence of three polar cyano groups and nonplanar conformation, these molecules selfassembled into a hydrogen-bonded organic framework (X-HOF-5) with distinct cavities capable of accommodating Tol molecules through multiple hydrogen-bonding interactions. Upon solvent removal via heating, the activated X-HOF-5 retained its cavity structure albeit with altered stacking arrangements, accompanied by a remarkable fluorescent color change from cyan to green. X-HOF-5a can undergo a phase transformation into X-HOF-5 upon reabsorption of Tol, while exhibiting no accommodation of Mcy due to the weak intermolecular interaction between PTTCN and Mcy. This suggests that the activated HOF material prefers Tol over Mcy. Moreover, X-HOF-5a may selectively accommodate Tol in a Tol/Mcy equimolar mixture, and the purity of Tol can reach 97% after release from the framework. Additionally, it is noteworthy that the HOF material exhibits recyclability without any discernible loss in performance.

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Section: Results and Discussionmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Luminescent Porous Organic Crystals for Adsorptive Separation of Toluene and Methylcyclohexane

Hu,

Zhao,

Liang

et al. 2024

ACS Appl. Mater. Interfaces

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“…Solvation free energy is defined as the energy change when a solute transitions from the gas phase to the liquid phase, revealing the strength of the solute–solvent interactions. Specifically, the greater the absolute value of solvation free energy, the stronger the molecular interactions between the solute and solvent, thereby increasing the solubility of 4FBA . Consequently, the solvation free energy can qualitatively explain differences in the solubility of 4FBA in different solvents.…”

Section: Resultsmentioning

confidence: 99%

“…Specifically, the greater the absolute value of solvation free energy, the stronger the molecular interactions between the solute and solvent, thereby increasing the solubility of 4FBA. 42 Consequently, the solvation free energy can qualitatively explain differences in the solubility of 4FBA in different solvents. Table 8 presents the solvation free energy of 4FBA in the selected pure solvents.…”

Section: Mixing Thermodynamic Propertiesmentioning

confidence: 99%

“…The reason for the higher solubility of 4FBA in acetone compared to ester solvents can be explained by the larger volume of ester molecules, which introduces steric hindrance affecting hydro-gen bond interactions and, consequently, solubility. In acetonitrile, the weak hydrogen bond donor−acceptor capabilities hinder strong interactions with 4FBA molecules, resulting in the lowest solubility 42.…”

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Revealing Solid–Liquid Equilibrium Behavior of 4-Fluorobenzoic Acid in 12 Pure Solvents from 283.15 to 323.15 K by Experiments and Molecular Simulations

Li,

Han,

Xiao

et al. 2024

J. Chem. Eng. Data

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The solubility of 4-fluorobenzoic acid (4FBA) in 12 pure solvents (methanol, ethanol, 1-propanol, 2-propanol, 1butanol, isobutanol, 1-pentanol, ethyl formate, methyl acetate, ethyl acetate, acetonitrile, and acetone) from 283.15 to 323.15 K at atmospheric pressure was determined using the gravimetric method. Within the experimental temperature range, the solubility of 4FBA increased with increasing temperature in all solvents. Four thermodynamic models (modified Apelblat model, NRTL model, Van't Hoff model, and λh model) were selected to correlate the experimental solubility data of 4FBA and assess the goodness of fit. The results revealed that the modified Apelblat equation exhibited the highest fitting accuracy. Furthermore, the mixing thermodynamic properties (mixing Gibbs free energy, mixing enthalpy, and mixing entropy) derived from the NRTL equation indicated that the mixing process of 4FBA in the selected solvents is spontaneous and entropy-driven. To elucidate the solid−liquid equilibrium behavior of 4FBA in pure solvents, the structural properties of the solute−solvent molecules were investigated. The physicochemical properties of solvents, solvation free energies, and radial distribution functions were studied to explain the solid− liquid equilibrium behavior of 4FBA.

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Solubility measurements, correlation, and thermodynamic characterization of 4-guanidinobenzoic acid hydrochloride in pure and binary solvents from 294.55 K to 333.65 K

Zhang,

Huang,

Peng

et al. 2024

The Journal of Chemical Thermodynamics

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Effects of intermolecular interactions and solvent properties on the solid-liquid phase equilibrium of isosorbide 5-mononitrate

Cited by 5 publications

References 33 publications

Luminescent Porous Organic Crystals for Adsorptive Separation of Toluene and Methylcyclohexane

Luminescent Porous Organic Crystals for Adsorptive Separation of Toluene and Methylcyclohexane

Revealing Solid–Liquid Equilibrium Behavior of 4-Fluorobenzoic Acid in 12 Pure Solvents from 283.15 to 323.15 K by Experiments and Molecular Simulations

Solubility measurements, correlation, and thermodynamic characterization of 4-guanidinobenzoic acid hydrochloride in pure and binary solvents from 294.55 K to 333.65 K

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