Uncovering the solubility behavior of vitamin B6 hydrochloride in three aqueous binary solvents by thermodynamic analysis and molecular dynamic simulation

Shi, Peng; Ma, Yiming; Han, Dandan; Du, Shichao; Zhang, Teng; Li, Zhonghua

doi:10.1016/j.molliq.2019.03.082

Cited by 46 publications

(11 citation statements)

References 41 publications

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“…Other necessary data relating to equilibrium solubility were obtained from previous work (Tang et al, 2015;Zhang et al, 2014) by the same measurement method. Details of the experimental apparatus and process of gravimetric analysis (Shi et al, 2019) are given in the supporting information and the solubility data are given in Table S1.…”

Section: Solubility Measurementmentioning

confidence: 99%

Probing the structural pathway of conformational polymorph nucleation by comparing a series of α,ω-alkanedicarboxylic acids

Shi

et al. 2020

IUCrJ

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Herein the nucleation pathway of conformational polymorphs was revealed by studying the relationships and distinctions among a series of α,ω-alkanedicarboxylic acids [HOOC–(CH2) n−2–COOH, named DAn, where n = 5, 7, 9, 11, 13, 15] in the solid state and in solution. Their polymorphic outcomes, with the exception of DA5, show solvent dependence: form I with conformation I crystallizes from solvents with hydrogen-bond donating (HBD) ability, whereas form II with conformation II crystallizes preferentially from solvents with no HBD ability. In contrast, form II of DA5 does not crystallize in any of the solvents used. Quantum mechanical computation showed that there is no direct conformational link between the solvents and the resultant polymorphic outcomes. Surprisingly, solute aggregates were found in no-HBD solvents by Fourier transform infrared spectroscopy, and only monomers could be detected in HBD solvents, suggesting stronger solvation. Furthermore, it was found that all six compounds including DA5 followed the same pattern in solution. Moreover, crystal-packing efficiency calculations and stability tests stated that dimorphs of DA5 bear a greater stability difference than others. These suggest that the rearrangement from conformation II to I could not be limited by hard desolvation in HBD solvents, where form I was also obtained. In other systems, metastable II was produced in the same solvents, probably as a result of the rearrangement being limited by hard desolvation. In this work, a comparative study uncovers the proposed nucleation pathway: difficulty in desolvation has a remarkable effect on the result of rearrangement and nucleation outcome.

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Section: Solubility Measurementmentioning

confidence: 99%

Probing the structural pathway of conformational polymorph nucleation by comparing a series of α,ω-alkanedicarboxylic acids

Shi

et al. 2020

IUCrJ

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“…In addition to the MOE molecular descriptors, the three kinds of solute–solvent interactions, API–water, API–ethanol, and API–water/ethanol, were taken into account by calculating the solvation free energy. Structure and energy optimization were performed by Materials Studio package, , and the further calculation of solvation free energy was carried out by COSMOthermX19 . For all of the following models, initial studies were conducted to evaluate model performance against the number of descriptors used.…”

Section: Methodsmentioning

confidence: 99%

Design of Spherical Crystallization of Active Pharmaceutical Ingredients via a Highly Efficient Strategy: From Screening to Preparation

Sun

Liu

et al. 2021

ACS Sustainable Chem. Eng.

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This work aims to develop a highly efficient spherical crystallization from screening to preparation stage based on liquid−liquid phase separation (LLPS). Mixtures than can undergo an LLPS split into two liquid phases with different physical properties, and the oil droplets formed during that process make LLPS a promising approach to prepare spherical particles of an active pharmaceutical ingredient (API). In the screening stage, three machine learning (ML) models (artificial neural network, support vector machine, and logistic regression) were established for predicting LLPS for an API. Two linear models, a simple linear model and a machine learning-based linear model, were also constructed to produce further optimization. The ML-based prediction of LLPS was first established in this work and showed high accuracy and reliability. Also, when compared to a method where the screening depended on the results of experiments, the prediction model highly reduced the use of chemical substances and saved labor and time. In the preparation stage, water and ethanol, which have low toxicity to mammals and have environmental advantages over other organic solvents, were applied as the solvents of LLPS-based spherical crystallization. The LLPS-based preparation process of spherical particles possesses advantages in terms of reduction of the number of unit operations as well as energy consumption and processing cost.

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“…The modified Apelblat equation is a semiempirical model, which is widely used to correlate the mole fraction solubility with temperature. It can be described as follows 15,16…”

Section: Methodsmentioning

confidence: 99%

“…The modified Apelblat equation is a semiempirical model, which is widely used to correlate the mole fraction solubility with temperature. It can be described as follows , where the values A , B , and C refer to the empirical constant. A and B values reflect the variation of activity coefficient and describe the nonideality of the real solution; the value C indicates the effect of temperature on fusion enthalpy.…”

Section: Thermodynamic and Correlating Modelsmentioning

confidence: 99%

Determination and Correlation of Solubility of Forms I and II of Imidacloprid in Seven Pure Solvents from 293.15 to 333.15 K

Wang

Shi

et al. 2020

J. Chem. Eng. Data

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The solubility of two forms of imidacloprid, forms I and II, in seven pure organic solvents was measured using the analytical gravimetric method. It was shown that the solubility of the two forms of imidacloprid increases as the temperature increases. Meanwhile, the solubility at a low temperature follows the order methyl acetate > ethyl acetate > n-butyl acetate > methanol > ethanol > n-propanol > n-butanol and the order at relatively high temperatures is methyl acetate > ethyl acetate > methanol > n-butyl acetate > ethanol > n-propanol > n-butanol. Differential scanning calorimetry and solubility data show that the two forms are monotropically related and form I is the stable phase. Besides, the experimental solubility of forms I and II in the seven pure solvents is well correlated by the modified Apelblat model and λh model, respectively.

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Uncovering the solubility behavior of vitamin B6 hydrochloride in three aqueous binary solvents by thermodynamic analysis and molecular dynamic simulation

Cited by 46 publications

References 41 publications

Probing the structural pathway of conformational polymorph nucleation by comparing a series of α,ω-alkanedicarboxylic acids

Probing the structural pathway of conformational polymorph nucleation by comparing a series of α,ω-alkanedicarboxylic acids

Design of Spherical Crystallization of Active Pharmaceutical Ingredients via a Highly Efficient Strategy: From Screening to Preparation

Determination and Correlation of Solubility of Forms I and II of Imidacloprid in Seven Pure Solvents from 293.15 to 333.15 K

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