Structurally Diverse Quantitative Structure−Property Relationship Correlations of Technologically Relevant Physical Properties

Katritzky, Alan R.; Maran, Uko; Lobanov, and Victor S.; Karelson, Mati

doi:10.1021/ci9903206

Cited by 241 publications

(201 citation statements)

References 209 publications

(372 reference statements)

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“…The flexibility index depends on (a) number of atoms, (b) the presence of rings, (c) branching, and (d) the presence of atoms with covalent radii smaller than those of C sp 3 .…”

Section: Discussionmentioning

confidence: 99%

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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.

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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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“…The flexibility index depends on (a) number of atoms, (b) the presence of rings, (c) branching, and (d) the presence of atoms with covalent radii smaller than those of C sp 3 .…”

Section: Discussionmentioning

confidence: 99%

“…The electrostatic contribution to the solvation processes in ethers is described by such polar surface areas as WNSA (1) , FPSA (2) , and FNSA (3) .…”

Section: Discussionmentioning

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.

Self Cite

100

152

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“…The molecular structure of a chemical determines its properties (Katritzky et al, 2000). Thus it is possible that the technology of quantitative structure-property relationships (QSPRs), which correlate and predict transport and transformation process data for organic pollutants from their structural descriptors, can be used to model and predict K OA values of PCBs.…”

Section: Introductionmentioning

confidence: 99%

Quantitative structure–property relationships for octanol–air partition coefficients of polychlorinated biphenyls

et al. 2002

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“…Physicochemical parameters are calculated using the computer software ChemSketch/ ACDlab program version 12.01 (Table 1). Octanol/water partition coefficient (logP) is the most frequently used measure of hydrophobicity (or lipophilicity) of chemicals, which, in turn, is a very important property in medicinal chemistry, toxicology, and pharmaceutical and environmental sciences [9] . Molar Volume refractive index, FW is the formula weight, δ is the density of the substance [10], [11] .Surface Tension …”

Section: Methodsmentioning

confidence: 99%

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2016

RJLBPCS

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QSAR study on 11 of 2,3-Diyne-1,4-naphthoquinone derivatives with anti-cancer activities IC50 has been made using seven physicochemical parameters to evaluate the chemicalbiological interactions. Multiple linear regression techniques were used to select the descriptors and to generate the several QSAR models and even in multi-parametric regression these physicochemical parameters don't give significant results but the mono-parametric regression shown that the cytotoxic activities of 2,3-Diyne-1,4-naphthoquinone derivatives depend on their hypophilictiy.

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Structurally Diverse Quantitative Structure−Property Relationship Correlations of Technologically Relevant Physical Properties

Cited by 241 publications

References 209 publications

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

Quantitative structure–property relationships for octanol–air partition coefficients of polychlorinated biphenyls

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