Solubility Measurement and Modeling of 5-Methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile (Y Form) in Pure and Binary Solvents

Wang, Jiayuan; Liang, Luyao; Zhu, Lingyu

doi:10.1021/acs.jced.2c00763

Cited by 2 publications

(14 citation statements)

References 37 publications

(47 reference statements)

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“…Wang et al reported a similar result. 8 The accuracy of PC-SAFT about the solubility prediction of ROY in pure organic solvents (the maximum ARD is 12.17% in acetone) was greater than in mixed solvents (the maximum ARD is 65.55% in acetone−water). However, in some cases, the accuracy of the prediction of drug solubility was reduced for two potential reasons.…”

Section: ■ Results and Discussionmentioning

confidence: 95%

“…In a previous work, Wang et al used temperature-independent binary interaction parameters k ij to model the solubility of ROY (5-methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile) in the pure and mixed solvents. 8 They suggested that using temperature-dependent k ij could potentially improve the fitting performance. Therefore, we chose the temperature-dependent k ij to model the solubility of OXA in different solvent systems to enhance the accuracy of the PC-SAFT model.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Recently, the thermodynamic theory PC-SAFT has successfully predicted the phase behavior between the drug and pure solvents or mixed solvents. 8 If coupled with other theories, it can explain the thermodynamic behavior of more complex systems. For example, Ge and Ji coupled the PC-SAFT theory with the micellar solubilization model and pH-dependent solubility model, predicting the solubility of drugs in micellar solution.…”

Section: ■ Introductionmentioning

confidence: 99%

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Measurement and Thermodynamic Modeling of Oxaprozin Solubility in Polymers and Mixed Solutions

Wu,

Jiang,

Shen

et al. 2024

J. Chem. Eng. Data

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Measuring and modeling the solubility of drugs in different solvent systems is helpful to guide the selection of appropriate solvents at various stages of drug formulation development. In this work, the gravimetrical method was used to determine the solubility data of oxaprozin (OXA) in different compositions of water/organic solvents (methanol and ethanol) binary mixtures within the range of 293.15 to 333.15 K. Subsequently, the differential scanning calorimetry method was used to measure the solubility of the drug in polymers (Polyethylene Glycol 6000 and Polyvinylpyrrolidone K30) at above 400 K. Then, the solubility of OXA in ultrapure water and polymer aqueous solution was acquired by UV spectrophotometry or HPLC within a temperature range of 303.15 to 323.15 K. Finally, the experimental values were compared with the calculated values from the Perturbed-Chain Statistical Associating Fluid Theory (PC-SAFT) to investigate the prediction accuracy of this model in different complex mixed solvent systems. The average relative deviations (ARD) were used to evaluate the model performance of PC-SAFT. Furthermore, PC-SAFT combined with solid−liquid equilibrium theory not only modeled the phase behavior between pure or mixed solvents and drugs independent of the molecular weight of the solvent but also did not require any experimental data or model parameters from the ternary system to predict the phase behavior of OXA in binary solvents. The results of this work illustrate that PC-SAFT is a beneficial model in drug development.

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Section: ■ Results and Discussionmentioning

confidence: 95%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

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Measurement and Thermodynamic Modeling of Oxaprozin Solubility in Polymers and Mixed Solutions

Wu,

Jiang,

Shen

et al. 2024

J. Chem. Eng. Data

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“…Color polymorphism originates from different electronic properties of the molecules of the compound in the different crystalline phases, which result mostly from different intermolecular interactions in the crystals between molecules exhibiting the same conformational state (packing polymorphism) or due to the presence of distinct conformers in the different crystals (conformational polymorphism) . Compounds may exhibit both conformational and packing polymorphisms, with ROY being a paradigmatic example of a substance that exhibits the two types of polymorphism. − Moreover, several studies have been recently published focusing on ROY, related compounds, and their remarkable color polymorphism properties. − …”

Section: Introductionmentioning

confidence: 99%

“…The parent compound of this family is 5-methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile (Scheme ), whose acronym ROY derives from the red, orange and yellow colors of its polymorphs. Presently, ROY is the compound possessing the largest number of identified and structurally characterized polymorphs: 12 in total. − …”

Section: Introductionmentioning

confidence: 99%

Unveiling the Red and Brownish-Green Polymorphs of a Novel ROY Derivative: 2-(4-((3-Cyanothiophen-2-yl)amino)-3-nitrophenyl)Acetic Acid

Nogueira,

Lopes,

Rodrigues

et al. 2024

Crystal Growth & Design

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Polymorphism has been the subject of many studies in the last decades, including a particular type of polymorphism where the colors exhibited by the polymorphs differ. However, only relatively limited or narrow differences in color were observed in color polymorphs of the same compound. Indeed, to this date, almost all compounds known to show color polymorphism exhibit red, orange, or yellow tones, as is the case of the notable ROY molecule (5-methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile), which is the compound with more polymorphs reported and structurally characterized hitherto. In this work, we report a new color polymorphic material derived from ROY, (2-(4-((3cyanothiophen-2-yl)amino)-3-nitrophenyl)acetic acid; or ROY-CAM), synthesized for the first time by nucleophilic aromatic substitution reaction between 2-(4-fluoro-3-nitrophenyl)acetic acid and 2-aminothiophene-3-carbonitrile, which exhibits a red (P2 1 / n, m.p.: 184 °C and θ = −4.4°and 3.0°) and a brownish-green polymorph (P1̅ , m.p.: 190 °C and θ = −66.1°). This is the first time a member of the ROY family of compounds was observed to exhibit a brownish-green polymorph and, more importantly, the first time that a molecular compound exhibits a red and a greenish polymorphs, i.e., this is the first example of an organic molecule that originates polymorphs covering such a wide range of color. The isolated molecule of ROY-CAM has 11 low-energy conformers, which were accessed by DFT calculations, with two of these conformers being identified in the observed polymorphs of the compound: in the brownish-green polymorph, the most stable conformer exists, while the red polymorph is composed of molecules assuming a conformation similar to that of the third most stable conformer. In the latter polymorph, the intramolecularly disfavored conformation assumed by the molecules is stabilized in the crystal lattice through interactions between carboxylic acid groups of neighboring molecules, resulting in dimeric units formed between pairs of the two distinct molecules that constitute the asymmetric unit of the crystal. The two identified polymorphs were characterized vibrationally (by both IR and Raman spectroscopies), and a thermal study is also presented (based on DSC, PLTM, and TGA measurements). Furthermore, the brownish-green and red colors exhibited by the polymorphs of ROY-CAM are explained based on the differences in the structures of the molecules that are present in these crystals.

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Solubility Measurement and Modeling of 5-Methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile (Y Form) in Pure and Binary Solvents

Cited by 2 publications

References 37 publications

Measurement and Thermodynamic Modeling of Oxaprozin Solubility in Polymers and Mixed Solutions

Measurement and Thermodynamic Modeling of Oxaprozin Solubility in Polymers and Mixed Solutions

Unveiling the Red and Brownish-Green Polymorphs of a Novel ROY Derivative: 2-(4-((3-Cyanothiophen-2-yl)amino)-3-nitrophenyl)Acetic Acid

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