Solubility Of Organic Compounds Research Articles

Introducing JCED Associate Editor Fleming Martinez and Topic Editor Christoph Held─Some Remarks on Reporting on the Solubility of Organic Compounds and of Electrolytes

ADVERTISEMENT RETURN TO ISSUEEditorialNEXTIntroducing JCED Associate Editor Fleming Martinez and Topic Editor Christoph Held─Some Remarks on Reporting on the Solubility of Organic Compounds and of ElectrolytesFleming MartinezFleming MartinezNational University of Colombia, Bogotá D. C., 571, ColombiaTU Dortmund University, Dortmund, 44227, GermanyUniversity of Minnesota, Minneapolis, Minnesota 55455, United StatesMore by Fleming Martinezhttps://orcid.org/0000-0002-4008-7273, Christoph HeldChristoph HeldNational University of Colombia, Bogotá D. C., 571, ColombiaTU Dortmund University, Dortmund, 44227, GermanyUniversity of Minnesota, Minneapolis, Minnesota 55455, United StatesMore by Christoph Heldhttps://orcid.org/0000-0003-1074-177X, and J. Ilja SiepmannJ. Ilja SiepmannNational University of Colombia, Bogotá D. C., 571, ColombiaTU Dortmund University, Dortmund, 44227, GermanyUniversity of Minnesota, Minneapolis, Minnesota 55455, United StatesMore by J. Ilja Siepmannhttps://orcid.org/0000-0003-2534-4507Cite this: J. Chem. Eng. Data 2023, 68, 6, 1265–1266Publication Date (Web):June 8, 2023Publication History Received15 May 2023Published online8 June 2023Published inissue 8 June 2023https://doi.org/10.1021/acs.jced.3c00278Copyright © Published 2023 by American Chemical SocietyRIGHTS & PERMISSIONSArticle Views-Altmetric-Citations-LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (2 MB) Get e-AlertscloseSUBJECTS:Electrolytes,Equilibrium,Organic compounds,Solubility,Solvents Get e-Alerts

Термофильное сбраживание бытовых пищевых отходов

In mesophilic conditions, anaerobic digestion is the most common in the world. However, thermophilic fermentation has several advantages due to the growth rate of microorganisms and the reactions they produce, as well as the degradation of deep organic matter due to an increase in the solubility of organic compounds. Increasing the temperature of the process makes it possible to neutralize the remnants of pathogenic organisms (viruses, bacteria, helminth eggs), which are necessary for the further use of fermented biomass as a biofertilizer. An effective inoculum is selected for the process of anaerobic co-fermentation of food waste and excess activated sludge. The optimal ratio of inoculate and substrate is determined to start the process of anaerobic digestion. Experiments with flasks and laboratory biogas reactors demonstrate that fermentation of OSV with food waste can significantly increase the rate and consumption of biogas. The optimal ratio of OSV and food waste in a mixture of coenzymes is 50/50, depending on the total content of organic substances in the mixture. The maximum rate of methanogenesis is observed in mixtures of I/C 70/30 and I/C 55/45 (after 18 days) and 156 ml of CH4 and 178 ml of CH4, respectively. This indicates the stability of the anaerobic process. It is shown that after pretreatment and activation of the landfill, the organic part of solid household waste, food waste and wastewater can be used to start the process of anaerobic digestion in anaerobic reactors.

Correlation analysis of the solubility of organic compounds: influence of the polarizability effect

Correlation analysis of the solubility of organic compounds: influence of the polarizability effect

Synthesis of 1-Phenylthiourea: An Undergraduate Organic Chemistry Experiment Illustrating Carbonyl Transformations

The practical two-step synthesis of 1-phenylthiourea is reported here as an undergraduate experiment for the organic synthesis laboratory. The reactions involved in 1-phenylthiourea preparation are very useful didactic examples to illustrate concepts relating to carbonyl substitution and addition, the effect of pH on solubility of organic compounds, and many laboratory techniques, such as isolation, purification, and product analysis. The products were purified through precipitation, which involves changing the pH value, followed by recrystallization. The products were identified by melting point and infrared and NMR spectroscopy.

CALCULATION OF ENVIRONMENTAL PROPERTIES FOR ORGANIC COMPOUNDS USING QUANTITATIVE STRUCTURE-SOLUBILITY RELATIONSHIPS

The solubility of organic compounds in water was related to the environmental behaviors. In this work, the solubility values of 27 organic compounds were calculated by using the different molecular descriptors. The quantitative structure-solubility relationships (QSSRs) were constructed by incorporating the multivariable technique and the genetic algorithm. The important molecular descriptors such as logP, SsCH3_acnt, ABSQ, nelem, nrings, SHBa, Gmax, Gmin, Xvp6, and Xvpc4 were selected to construct the linear models QSSRs with the genetic algorithm. The best four-variable linear model QSSR was obtained from those descriptors. The quality of QSSR linear model indicated in statistical values R2training of 96.60, standard error of estimation, SE of 0.2961, F-statistic of 156.0, P-value of 0.0, R2test of 95.02, and RSS value of 2.823. The architecture of neural network I(4)-HL(4)-O(1) with R2training of 99.03 was constructed by the molecular descriptors in the four-variable linear model. The predicted solubility values of organic substances in test group resulting from these models are in good agreement with those from literature.

Solubility of organic compounds in octanol: Improved predictions based on the geometrical fragment approach

Two new models are introduced to predict the solubility of chemicals in octanol (Soct), taking advantage of the extensive character of log(Soct) through a decomposition of molecules into so-called geometrical fragments (GF). They are extensively validated and their compliance with regulatory requirements is demonstrated. The first model requires just a molecular formula as input. Despite an extreme simplicity, it performs as well as an advanced random forest model involving 86 descriptors, with a root mean square error (RMSE) of 0.64 log units for an external test set of 100 molecules. For the second one, which requires the melting point Tm as input, introducing GF descriptors reduces the RMSE from about 0.7 to <0.5 log units, a performance that could previously be obtained only through the use of Abraham descriptors. A script is provided for easy application of the models, taking into account the limits of their applicability domains.

Solubility of 3-{3,5-Bis(trifluoromethyl)phenyl}quinoline Using Micellar Solutions of Surfactants

Amphiphilic substances, surfactants, are in common use to enhance the aqueous solubility of organic compounds. Solubilization of 3-{3,5-bis (trifluoromethyl)phenyl}quinoline was investigated by employing spectrophotometry, light scattering and tensiometry in micellar solutions of nonionic surfactants {dimethyldodecylamine-N-oxide, DDAO; polyoxyethylene(23)lauryl ether, Brij35; and polyoxyethylene(04)lauryl ether, Brij30}, a cationic surfactant (dodecyltrimethyl-ammonium bromide, DTAB), anionic surfactants (sodium dodecylbenzenesulfonate, SDBS; sodium dodecyl sulfate, SDS), and a zwitterionic surfactant (N-dodecyl-N,N-dimethyl-3-ammonio-1-propanesulfonate, DDAPS). It is noted that the solubility of the title compound 3-{3,5-bis (trifluoromethyl)phenyl}quinoline increased linearly with the increase in surfactant concentration irrespective of the type of surfactant. This is due to association of the title compound with surfactants. The molar solubilization ratio (MSR), micelle–water partition coefficient (KM), and the Gibbs energy of solubilization (\( \Delta G_{\text{S}}^{\text{o}} \)) of the title compound in the micelles were determined and correlated with each other. The nonionic surfactant DDAO showed the highest solubilization capacity. The order of degree of solubility among nonionic, cationic, and anionic surfactants for 3-{3,5-bis (trifluoromethyl)phenyl}quinoline is DDAO > DDAPS > SDBS > DTAB > SDS > Brij35 > Brij30. This comparative study can be used to select an appropriate medium for the title compound’s solubilization, where the nonionic surfactants DDAO, Brij35 and Brij30 would be more beneficial due to their minimal protein binding and retention of their micellar form even after large dilution in blood owing to their very low critical micellar concentration values. The light scattering study indicated that the hydrodynamic radius of the blank and drug-loaded surfactants remained the same within experimental error.

Prediction of cosolvent effect on solvation free energies and solubilities of organic compounds in supercritical carbon dioxide based on fully atomistic molecular simulations.

The solubility of organic compounds in supercritical fluids can be dramatically affected by addition of a suitable cosolvent (entrainer) at small concentrations. This makes the screening of the best-suited cosolvent an important task for the supercritical technology. The present study aims to improve our fundamental understanding of solvation in supercritical CO2 with cosolvents. We address the following questions: (1) How does the solvation free energy depend on the chemical class of an organic solute and the chemical nature of co-solvents? (2) Which intermolecular interactions determine the effect of a cosolvent on the solubility of organic compounds? We performed extensive calculations of solvation free energies of monofunctional organic molecules at infinite dilution in supercritical media by the Bennett's acceptance ratio method based on fully atomistic molecular dynamics sampling. Sixteen monofunctional organic molecules were solvated in pure sc-CO2 and sc-CO2 with addition of 6 molar % of cosolvents of different chemical nature: ethanol, acetone, and n-hexane. Cosolvent-induced solubility enhancement (CISE) factors were also calculated. It was found that formation of significant number of hydrogen bonds between a solute and cosolvent molecules leads to a profound solubility enhancement. The cosolvent effect is proportional to the number of hydrogen bonds. When polar cosolvents do not form hydrogen bonds with solutes, the CISE correlates with the dipole moment of solute molecules. However, the electrostatic interactions have a small impact on the solubility enhancement compared to hydrogen bonding. Addition of a nonpolar cosolvent, n-hexane, has a very little effect on the solvation Gibbs free energy of studied small organic molecules. The observed trends were discussed in line with available experimental data.

(Solid + liquid) solubility of organic compounds in organic solvents – Correlation and extrapolation

A semi-empirical model is developed for the regression of (solid+liquid) solubility data with temperature. The model fulfils the required boundary conditions, allowing for robust extrapolation to higher and lower temperatures. The model combines a representation of the solid-state activity which accommodates a temperature-dependent heat capacity difference contribution with a scaled three-parameter Weibull function representing the temperature dependence of the solution activity coefficient at equilibrium. Evaluation of the model is based on previously published experimental calorimetric and solubility data of four organic compounds, fenoxycarb, fenofibrate, risperidone and butyl paraben, in five common organic solvents, methanol, ethyl acetate, acetone, acetonitrile, and toluene. The temperature dependence of the van’t Hoff enthalpy of solution and its components is analysed and discussed. Among the four compounds the influence of temperature on the enthalpy of fusion varies from moderate to substantial. Based on the semi-empirical model, a new equation containing three adjustable parameters is proposed for regression and extrapolation of solubility data for cases when only melting data and solubility data is available. The equation is shown to provide good accuracy and robustness when evaluated against the full semi-empirical model as well as against commonly used, more simple empirical equations. It is shown how such a model can be used to obtain an estimate of the heat capacity difference for cases where accurate solubility data is available in multiple solvents.

Contextualizando reações ácido-base de acordo com a teoria protônica de Brönsted-Lowry usando comprimidos de propranolol e nimesulida

This paper reports the use of alternative materials for teaching experimental chemistry. In this context, nimesulide and propranolol tablets were used to teach chemical concepts about acid-base reactions according to Bronsted-Lowry protonic Theory. Important topics of Organic, Analytical and Pharmaceutical Chemistry were discussed, such as purification by acid-base extraction, solubility of organic compounds in aqueous solutions, buffers, the dissociation constant (pKa), potentiometric titration and ionization of drugs in biological fluids. The purification of propranolol and nimesulide from tablets produced yields of 75% and 90%, respectively. The experimental values of pKa for both drugs were in agreement with those from the literature.

Solubilidade das substâncias orgânicas

The solubility of organic compounds is a topic of great importance in chemistry and of interest in several areas, such as materials, drugs and the environment. In this paper, the solubility of these species is discussed in terms of their properties, such as the predominant type of chemical bond, molecular structure, polarity and types of intermolecular interactions. Examples of biological processes fundamental for sustainability of life and related with the solubility of chemical species are presented and discussed.

Combined effects of salinity and temperature on the solubility of organic compounds

This study deals with the solubility limits of organic liquids liable to be spilled at sea during ship-wrecking or other incidents at sea. The effects under consideration are induced by both salinity and temperature. The former is described through use of the Setchenov relationship, and the latter by using the Van’t Hoff equation. A coupling of both relationships led to an equation applicable to scarcely soluble liquids and expressed in a simplified form usable in decision-support systems as a result of the choice of the reference state when writing the thermodynamic relationships. The mathematical relation we found was tested on experimental data about four compounds, i.e. dimethyldisulfide (DMDS), methyl methacrylate (MMA), 1-butanol (1-But), and methyl ethyl ketone (MEK), chosen because of their wide use in the industry and frequent transport by sea. All of them were studied at four salinity values and five temperatures, and the mathematical relation under test proved to be quite satisfactory.

QSPRModel Analysis on the Solubility of Organic Compounds in Ionic Liquids

A quantitative structure-property relationship(QSPR) study on the solubility of 84 organic compounds in 4 different ionic liquids was done based on VolSurf parameters using the partial least square(PLS) statistical method and good results were obtained.The training set model predicts the solubilities of the test set well.An analysis of the VolSurf descriptors show that large volume hydrophilic regions are beneficial for solubility,and the interaction energy is about -0.84 kJ·mol-1 between the organic compounds and the ionic liquids.A certain degree of hydrophobicity is also favorable for solubility.When the ionic liquids have a small hydrophobic substituent,an asymmetric partial hydrophobic region in the organic compound is advantageous for solubility.If the ionic liquid has a large hydrophobic substituent,a large hydrophobic region in the organic compound benefits the solubility.Multiple linear regression(MLR) analysis shows that hydrophilic parameter W1 is the most important parameter,which indicates that hydrophilicity is a key factor that influences the solubility of organic compounds in ionic liquids.

Solubility of hydrophobic compounds in water–cosolvent mixtures: Relation of solubility with water–cosolvent interactions

The solubility of organic compounds in mixtures of water and an organic cosolvent can be reasonably estimated from the solubility values in the neat solvents and the composition of the solvent mixture, by means of the log-linear solubilization model. However, deviations from the model are frequently observed in different degree. Such deviations, which tend to become more pronounced with decreasing polarity of the cosolvent, are to a good extent the result the nonideal mixing of water and cosolvent, due to the interactions between the two solvent components. We present a model that incorporates the effect of water–cosolvent interactions into the log-linear model. The effect of nonideality of mixing takes the form of a pseudoquadratic expression on the cosolvent concentration, obtainable from vapor pressure data of the solute-free water–cosolvent mixture. © 2009 Wiley-Liss, Inc. and the American Pharmacists Association J Pharm Sci 99:293–302, 2010

Computational Approaches to Estimating Octanol-Water Partition Coefficient and Water Solubility of Organic Compounds

Octanol-water partition coefficient and water solubility are two important physicochemical properties of organic compounds in medicinal chemistry and environmental chemistry studies.They are used as critical parameters in quantitative structure-activity relationship (QSAR) studies to model the adsorption, distribution and metabolism of drugs in the living body and the distribution of organic compounds in naturenvironment.The most widely applied approaches to calculating octanol-water partition coefficients and water solubility can be roughly divided into two categories:fragment-addition models and descriptor-based models.This article provides a comprehensive review on these approaches, discusses their strengths and shortcomings, and provides an outlook for possible future developments in this area.

Arginine Increases the Solubility of Coumarin: Comparison with Salting-in and Salting-out Additives

Poor aqueous solubility of low molecular weight drug substances hampers their development as pharmacological agents. Here, we have examined the effects of arginine on the solubility of organic compounds, coumarin, caffeine and benzyl alcohol, in aqueous solution. Arginine increased the solubility of aromatic coumarin, but not non-aromatic caffeine, concentration dependently, suggesting the favourable interaction of arginine with the aromatic structure. Consistent with this, arginine also increased the solubility of aromatic benzyl alcohol. Guanidine hydrochloride, urea and salting-in salts increased both coumarin and caffeine solubilities, while salting-out salts decreased them. These results suggest the specific interaction of arginine with aromatic groups, leading to increased solubility of coumarin. However, the effect of 1 M arginine on coumarin solubility was at most approximately 2-fold, which may limit its applications as a solubility enhancing agent.

Recurrent relations for the approximation of the physicochemical constants of homologues

In addition to the earlier revealed physicochemical constants of homologues whose changes in arbitrary series obey the simplest linear recurrent relations A (n + k) = aA(n) + b, such equations are shown to be applicable to the approximation of the solubility of organic compounds in water (k = 1), temperature dependences of the solubility of organic and inorganic compounds in water (k = ΔT), and nematic-isotropic phase transition temperatures for liquid crystals (k = 2). The a and b coefficients of linear recurrent relations are only determined by the nature of the homologous difference, and, if the homologous difference is the same, they are close for different series. This enables various properties of virtually arbitrary organic compounds to be described by unified recurrent equations, which is equivalent to the existence of a general method for their calculation. For continuous properties (for the example of the temperature dependence of solubility), a method for solving recurrent equations with nonintegral or nonequidistant argument values is suggested.

Solubility Screening on a Series of Structurally Related Compounds: Cosolvent-Induced Changes on the Activity Coefficient of Hydrophobic Solutes

A homologous series of solutes was chosen as a model for a group of structurally related compounds with different physicochemical properties, as is commonly the case during the screening of potential drug candidates. Thermal properties of the crystalline solutes and solubility determinations were used to quantify the two independent factors that determine the solubility of organic compounds: crystallinity and hydrophobicity. A solubility screening study was conducted on the series. By expressing the obtained solubility enhancement expressed as changes in the activity coefficient, it is possible to visually compare the effect of different cosolvents. The results show the importance of solute-solvent polarity match. Polarity match between water miscible cosolvents and hydrophobic compounds is not truly attainable, but comparison of the screening results points out the closest matches (optimal effect), facilitating the systematic evaluation of solubilization approaches.

The Solubility of Organic Compounds in Supercritical CO2

A simple liquid solution model is proposed to describe the effect of solvent-solute interactions on the solubility of nonpolar and slightly polar substances in supercritical solvents. Treating the system as an ideal solution, the effect of pressure on the solubility is zero or nearly zero, as it is governed by the difference in molar volume of the pure supercooled liquid solute and the pure solid solute, and this may be nearly zero. Deviations from ideal behavior are given by activity coefficients of the Margules type with the interaction parameter w interpreted as interchange energy as in the lattice theory. The hypothesis is put forward that the interchange energy is of the same form as a function proposed by Liptay and others to describe the effect of the solvent on the wavelength of the absorption maximum of the solute dissolved in the solvent. The function consists of a radius of interaction a and a function g(ε ) of the dielectric constant ε of the solvent, treated as a continuum. The function g depends on pressure through the pressure dependence of the dielectric constant ε (P). The attractive feature of this formalism, introduced by Baumann et al. and here justified thermodynamically, is that plots of the logarithm of solubility vs. g are linear, except for polar solutes near the solvent’s critical point. Changes in slope then admit interpretation as changes in the radius of interaction a with possible clues about the mechanism of solvation of these molecules.

Linear and Nonlinear Methods in Modeling the Aqueous Solubility of Organic Compounds.

Linear and Nonlinear Methods in Modeling the Aqueous Solubility of Organic Compounds.