Determination of olive oil–gas and hexadecane–gas partition coefficients, and calculation of the corresponding olive oil–water and hexadecane–water partition coefficients

We present an extended QSPR modeling of solubilities of about 500 substances in series of up to 69 diverse solvents. The models are obtained with our new software package, CODESSA PRO, which is furnished with an advanced variable selection procedure and a large pool of theoretically derived molecular descriptors. The squared correlation coefficients and squared standard deviations (variances) range from 0.837 and 0.1 for 2-pyrrolidone to 0.998 and 0.02 for dipropyl ether, respectively. The predictive power of the models was verified by using the "leave-one-out" cross-validation procedure. The QSPR models presented are suitable for the rapid evaluation of solvation free energies of organic compounds. BACKGROUND TO THE PRESENT SERIES OF PAPERSSolubility is of the utmost significance in numerous areas of human endeavor and interest. Solubility in water is fundamental to environmental issues such as pollution, erosion, and mass transfer. Solubility in organic solvents forms much of the basis of the chemical industry. Solubility determines shelf life and cross contamination. It is critically linked to bioavailability and thus to the effectiveness of pharmaceuticals, biodegradation, suitability of gaseous anesthetics, blood substitutes, oxygen carriers, etc. Toxicity is critically dependent on solubility.Very extensive studies have been carried out on the solubilities of various solute-solvent pairs resulting in diverse theories of solute-solvent interactions that form the basis of our knowledge for the understanding of solubility. 1 These theories are based on concepts ranging from quantitative analysis to statistical mechanics and quantum mechanics. Quantitative treatments of solute-solvent interactions in series of compounds have gained wide attraction and have led to various models for explaining solute-solvent behavior. 2 Most of this work has involved studying a series of solutes dissolved in a single solvent. There are some instances in which the solubilities of a solute in a series of solvents have been examined, as reviewed elsewhere. 3,4 Many of the previous studies provide valuable contributions to the understanding of the general phenomena of solute-solvent interactions. In depth comparisons of published data series have revealed that many gaps exist, which render impossible any general comparison of solvent-solute pairs utilizing only experimental data. Therefore we have proposed the combination of quantitatiVe structure-property/actiVity relationship analysis and subsequent principal component analysis for the general treatment of solubility. 5 A common procedure in quantitative structure-property/ activity relationships (QSPR/QSAR) analysis is the application of variable selection methods such as stepwise forward selection, 6,7 genetic algorithms, 8,9 and simulated annealing 10,11 for the reduction of descriptor space in order to keep the only most influential descriptors for the prediction of a property (in the present instance solubility). In this first version of our general treatment of solubility w...

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“…Publications of Abraham 37,57 are another important source of information, especially with solubilities in hexadecane and alcohols.…”

Section: Datamentioning

confidence: 99%

A General Treatment of Solubility. 1. The QSPR Correlation of Solvation Free Energies of Single Solutes in Series of Solvents

Katritzky

Oliferenko²,

Oliferenko³

et al. 2003

J. Chem. Inf. Comput. Sci.

152

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“…(8) and (9) for the 18 refrigerants listed in Table 23, so that it is possible to calculate log(1/NPT) and (1/EIT) values. The corresponding NPT and EIT values themselves are in Table 25 together with observed values for a selection of other solutes.…”

Section: Estimation Of Physicochemical and Biochemical Propertiesmentioning

confidence: 99%

“…It is again straightforward to insert the relevant values of the descriptors into Eqs. (8) and (9) to deduce the chemosensory properties.…”

Section: Estimation Of Physicochemical and Biochemical Propertiesmentioning

confidence: 99%

“…The dependent variable, log SP, is some property of a series of solutes in a fixed phase, and the independent variables, or descriptors, are solute properties as follows: R 2 is an excess molar refraction [4], π 2 H is the solute dipolarity/polarizability [5], ∑α H 2 and ∑β 2 H are, respectively, the solute overall hydrogen bond acidity and basicity [6]. Vx is the MacGowan characteristic volume in units of (dm 3 mol -1 /100) [7] and logL 16 is a descriptor, where L 16 is the solute gas-hexadecane partition coefficient at 298 K [8]. The first four descriptors can be regarded as measures of the tendency of a solute to undergo various solute-solvent interactions, all of which are energetically favorable, i.e.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Solvation properties of refrigerants, and the estimation of their water–solvent and gas–solvent partitions

Abraham

Gola

Cometto‐Muñiz

et al. 2001

Fluid Phase Equilibria

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We have previously used two general solvation equations to correlate and to interpret a wide variety of physicochemical and biochemical properties of compounds (solutes). Application of these equations requires a knowledge of the relevant solute descriptors, viz. R 2 , the excess molar refraction, π 2 H , the solute dipolarity/polarizability, ∑α H 2 , ∑β 2 H , the solute overall hydrogen bond acidity and basicity, and logL 16 , where L 16 is the solute gas-hexadecane partition coefficient at 298 K. We have also shown that these solute descriptors can be obtained from partition coefficients of solutes in various water-solvent and gas-solvent systems. Here, we use this approach to calculate solute descriptors for a series of 18 organofluorocarbons, classed as refrigerants, including chlorofluorocarbons, hydrochlorofluorocarbons, hydrofluorocarbons and perfluorocarbons, using Henry's law coefficients in water and five organic solvents that we have already measured. These data have been used to calculate Ostwald solubility coefficients, log L. Gas-water and gas-solvent partitions have been then combined to give log P for partition between water and solvent. A number of log P and L values have also been taken from the Medchem97 database. There are enough data to obtain the above descriptors for the 18 organofluorocarbons, and then to estimate log P and L values in a large number of other solvents. The chemosensory properties of the organofluorocarbons are also estimated.

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“…For this reason, it was decided to use the above-described experimental procedure that allows the separation of the adsorption contribution. To quantify intermolecular solute-IL interactions, we used the LSER equation developed by Abraham et al (Abraham et al, 1987, 1990, 1991, Abraham, 1993. This method allows one to correlate thermodynamic properties of phase transfer processes.…”

Section: Thermodynamics Datamentioning

confidence: 99%

Ionic Liquids from (Meth) Acrylic Compounds

Sindt¹,

Mieloszynski²,

Harmand³

2011

Ionic Liquids - Classes and Properties

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Determination of olive oil–gas and hexadecane–gas partition coefficients, and calculation of the corresponding olive oil–water and hexadecane–water partition coefficients

Cited by 214 publications

References 1 publication

A General Treatment of Solubility. 1. The QSPR Correlation of Solvation Free Energies of Single Solutes in Series of Solvents

A General Treatment of Solubility. 1. The QSPR Correlation of Solvation Free Energies of Single Solutes in Series of Solvents

Solvation properties of refrigerants, and the estimation of their water–solvent and gas–solvent partitions

Ionic Liquids from (Meth) Acrylic Compounds

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