Solubility and dissolution thermodynamic properties of 2-Cyano-4′-methylbiphenyl in binary solvent mixtures

Zhou, Yanan; Wang, Jingkang; Fang, Binbin; Guo, Nannan; Xiao, Yan; Hao, Hongxun; Bao, Ying; Huang, Xin

doi:10.1016/j.molliq.2017.04.049

Cited by 12 publications

(6 citation statements)

References 22 publications

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“…The main source for these values was found in the comprehensive collection of Chickos, Acree and Liebman [ 21 ] and in its update [ 60 ]. More recent entropy-of-fusion data were found for long-chain fluorinated alcohols [ 33 ], halogenated fluorenes [ 35 ], di- and tri(cyanatophenyl)alkanes and -silanes [ 62 ], 2-cyano-4′-methylbiphenyl [ 83 ], diphenyl cyclohexyl-phosphoramidate [ 84 ] and 3,4-dinitrofurazanfuroxan [ 85 ]. The complete set of compounds with experimental entropy-of-fusion values amounted to a total of 2809 used for the evaluation of the atom-group parameters, yielding 188 valid atom groups.…”

Section: Resultsmentioning

confidence: 99%

Calculation of Five Thermodynamic Molecular Descriptors by Means of a General Computer Algorithm Based on the Group-Additivity Method: Standard Enthalpies of Vaporization, Sublimation and Solvation, and Entropy of Fusion of Ordinary Organic Molecules and Total Phase-Change Entropy of Liquid Crystals

Naef

Acree

2017

Molecules

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The calculation of the standard enthalpies of vaporization, sublimation and solvation of organic molecules is presented using a common computer algorithm on the basis of a group-additivity method. The same algorithm is also shown to enable the calculation of their entropy of fusion as well as the total phase-change entropy of liquid crystals. The present method is based on the complete breakdown of the molecules into their constituting atoms and their immediate neighbourhood; the respective calculations of the contribution of the atomic groups by means of the Gauss-Seidel fitting method is based on experimental data collected from literature. The feasibility of the calculations for each of the mentioned descriptors was verified by means of a 10-fold cross-validation procedure proving the good to high quality of the predicted values for the three mentioned enthalpies and for the entropy of fusion, whereas the predictive quality for the total phase-change entropy of liquid crystals was poor. The goodness of fit (Q2) and the standard deviation (σ) of the cross-validation calculations for the five descriptors was as follows: 0.9641 and 4.56 kJ/mol (N = 3386 test molecules) for the enthalpy of vaporization, 0.8657 and 11.39 kJ/mol (N = 1791) for the enthalpy of sublimation, 0.9546 and 4.34 kJ/mol (N = 373) for the enthalpy of solvation, 0.8727 and 17.93 J/mol/K (N = 2637) for the entropy of fusion and 0.5804 and 32.79 J/mol/K (N = 2643) for the total phase-change entropy of liquid crystals. The large discrepancy between the results of the two closely related entropies is discussed in detail. Molecules for which both the standard enthalpies of vaporization and sublimation were calculable, enabled the estimation of their standard enthalpy of fusion by simple subtraction of the former from the latter enthalpy. For 990 of them the experimental enthalpy-of-fusion values are also known, allowing their comparison with predictions, yielding a correlation coefficient R2 of 0.6066.

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Section: Resultsmentioning

confidence: 99%

Calculation of Five Thermodynamic Molecular Descriptors by Means of a General Computer Algorithm Based on the Group-Additivity Method: Standard Enthalpies of Vaporization, Sublimation and Solvation, and Entropy of Fusion of Ordinary Organic Molecules and Total Phase-Change Entropy of Liquid Crystals

Naef

Acree

2017

Molecules

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show abstract

“…The main source for these values was found in the comprehensive collection of Chickos, Acree and Liebman [21] and in its update [60]. More recent entropy-of-fusion data were found for long-chain fluorinated alcohols [33], halogenated fluorenes [35], di-and tri(cyanatophenyl)alkanes and -silanes [62], 2-cyano-4′-methylbiphenyl [83], diphenyl cyclohexyl-phosphoramidate [84] and 3,4-dinitrofurazanfuroxan [85]. The complete set of compounds with experimental entropy-of-fusion values amounted to a total of 2809 used for the evaluation of the atom-group parameters, yielding 188 valid atom groups.…”

Section: Entropy Of Fusionmentioning

confidence: 99%

Calculation of Five Thermodynamic Molecular Descriptors by Means of a General Computer Algorithm Based on the Group-Additivity Method: Standard Enthalpies of Vaporization, Sublimation and Solvation, and Entropy of Fusion of ordinary Organic Molecules and Total Phase-Change Entropy of Liquid Crystals

Naef

Acree

2017

Preprint

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Abstract:The calculation of the standard enthalpies of vaporization, sublimation and solvation of organic molecules is presented using a common computer algorithm on the basis of a group-additivity method. The same algorithm is also shown to enable the calculation of their entropy of fusion as well as the total phase-change entropy of liquid crystals. The present method is based on the complete break-down of the molecules into their constituting atoms and their immediate neighbourhood; the respective calculations of the contribution of the atomic groups by means of the Gauss-Seidel fitting method is based on experimental data collected from literature. The feasibility of the calculations for each of the mentioned descriptors was verified by means of a 10-fold cross-validation procedure proving the good to high quality of the predicted values for the three mentioned enthalpies and for the entropy of fusion, whereas the predictive quality for the total phase-change entropy of liquid crystals was poor. The goodness of fit (Q 2 ) and the standard deviation (σ) of the cross-validation calculations for the five descriptors was as follows: 0.9641 and 4.56 kJ/mol (N=3386 test molecules) for the enthalpy of vaporization, 0.8657 and 11.39 kJ/mol (N=1791) for the enthalpy of sublimation, 0.9546 and 4.34 kJ/mol (N=373) for the enthalpy of solvation, 0.8727 and 17.93 J/mol/K (N=2637) for the entropy of fusion and 0.5804 and 32.79 J/mol/K (N=2643) for the total phase-change entropy of liquid crystals. The large discrepancy between the results of the two closely related entropies is discussed in detail. Molecules, for which both the standard enthalpies of vaporization and sublimation were calculable, enabled the estimation of their standard enthalpy of fusion by simple subtraction of the former from the latter enthalpy. For 990 of them the experimental enthalpy-of-fusion values are also known, allowing their comparison with predictions, yielding a correlation coefficient R 2 of 0.6066.

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“…In addition, the size of crystals obtained at the ratio of 1:2 is more homogeneous than that obtained under 1:3, which also has a narrower crystal size distribution. However, as the yield of reverse antisolvent crystallization process mainly depends on the volume ratio of solution to antisolvent, which can be interpreted in terms of solubility data of carnosine . The yield decreases apparently with the increasing of the mole fraction of ethanol.…”

Section: Resultsmentioning

confidence: 99%

“…In this study, a reverse antisolvent crystallization method was used to produce spherulite formation of carnosine, and the spherical crystals of carnosine were first obtained. In the reverse antisolvent crystallization process, a carnosine solution was added to the antisolvent to reach high supersaturation at the beginning of the experiment, which can drive the formation of carnosine spherical crystals. , Besides, the solubility of carnosine, which provides essential information for the crystallization process, , was measured at a temperature ranging from 288.05 to 323.15 K by using a gravimetric method under atmospheric pressure to design and optimize the spherical crystallization technology of carnosine. To extend the applicability of the solubility data, the modified Apelblat equation and the Jouyban-Acree model were used to correlate and analyze the experimental solubility data of carnosine.…”

Section: Introductionmentioning

confidence: 99%

Self-Assembly of Monodispersed Carnosine Spherical Crystals in a Reverse Antisolvent Crystallization Process

Zhou

Wang

et al. 2019

Crystal Growth & Design

Self Cite

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Spherical crystallization is an effective way to increase particle size, raise bulk density, and improve flowability and compressibility of crystals with small sizes, especially needle-like and flake-like microcrystals. In this work, a reverse antisolvent crystallization method was used to obtain the spherical crystals of carnosine instead of commercially available needle-like carnosine material. Besides, the solubility of carnosine in a binary solvent mixture of water + ethanol was measured at temperatures ranging from 288.05 to 323.15 K by using a gravimetric method under atmospheric pressure to optimize this crystallization process and increase the yield of carnosine. On the basis of these thermodynamic data, single factor analysis in a reverse antisolvent crystallization process was performed, including carnosine aqueous solution concentration, feeding rate, volume ratio of solution to antisolvent, temperature, and stirring speed. Polarizing microscopy, particle size distributions, and in situ particle vision measurements were used to characterize and monitor the carnosine spherical crystals during the reverse antisolvent crystallization process. Finally, monodispersed, several hundred micrometer-sized carnosine spherical crystals with a higher bulk density (0.224 g/mL) and smaller repose angle (39°), which indicated better flowability, were successfully crystallized, and a feasible formation mechanism was proposed.

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Solubility and dissolution thermodynamic properties of 2-Cyano-4′-methylbiphenyl in binary solvent mixtures

Cited by 12 publications

References 22 publications

Calculation of Five Thermodynamic Molecular Descriptors by Means of a General Computer Algorithm Based on the Group-Additivity Method: Standard Enthalpies of Vaporization, Sublimation and Solvation, and Entropy of Fusion of Ordinary Organic Molecules and Total Phase-Change Entropy of Liquid Crystals

Calculation of Five Thermodynamic Molecular Descriptors by Means of a General Computer Algorithm Based on the Group-Additivity Method: Standard Enthalpies of Vaporization, Sublimation and Solvation, and Entropy of Fusion of Ordinary Organic Molecules and Total Phase-Change Entropy of Liquid Crystals

Calculation of Five Thermodynamic Molecular Descriptors by Means of a General Computer Algorithm Based on the Group-Additivity Method: Standard Enthalpies of Vaporization, Sublimation and Solvation, and Entropy of Fusion of ordinary Organic Molecules and Total Phase-Change Entropy of Liquid Crystals

Self-Assembly of Monodispersed Carnosine Spherical Crystals in a Reverse Antisolvent Crystallization Process

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