Experimental solubilities were determined for 31 solid nonelectrolyte organic compounds dissolved in tert-butyl acetate at 298.15 K. Results of the experimental measurements were combined with published mole fraction solubility data for two lipid-lowering medicinal compounds (lovastatin and simvastatin) in order to derive Abraham model expressions for solute transfer into the tert-butyl acetate mono-solvent. The derived correlations provided an accurate mathematical description of the observed experimental data. As part of the current study, previously published Abraham model solvent correlations for both ethyl acetate and butyl acetate were updated using much larger datasets that contained an additional 64 and 35 experimental data points, respectively. The mathematical correlations presented in the current study describe the observed solubility ratios of solutes dissolved in tert-butyl acetate, ethyl acetate, and butyl acetate to within an overall standard deviation of 0.15 log units or less.

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Development of Abraham Model Correlations for Solute Transfer into the tert-Butyl Acetate Mono-Solvent and Updated Equations for Both Ethyl Acetate and Butyl Acetate

Development of Abraham Model Correlations for Describing Solute Transfer into Transcutol Based on Molar Solubility Ratios for Pharmaceutical and Other Organic Compounds

Determination of Abraham Model Solute Descriptors for N-Hydroxyphthalimide: An Organic Compound Having a N-Hydroxy (N–OH) Functional Group

Abraham model solute descriptors are reported for the first time for 62 additional C10 through C13 methyl- and ethyl-branched alkanes. The numerical values were determined using published gas chromatographic retention Kováts retention indices for 157 alkane solutes eluted from a squalane stationary phase column. The 95 alkane solutes that have known descriptor values were used to construct the Abraham model KRI versus L-solute descriptor correlation needed in our calculations. The calculated solute descriptors can be used in conjunction with previously published Abraham model correlations to predict a wide range of important physico-chemical and biological properties. The predictive computations are illustrated by estimating the air-to-polydimethylsiloxane partition coefficient for each of the 157 alkane solutes.

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Determination of Abraham Model Solute Descriptors for 62 Additional C10 through C13 Methyl- and Ethyl-Branched Alkanes

ABSTRACT Mole fraction solubilities are reported for 2-naphthoxyacetic acid dissolved in three alkanol (3-methyl-1-butanol, 2-pentanol, 1-octanol), two alkyl alkanoate (tert-butyl acetate, methyl butyrate), three alkanone (butanone, 2-pentanone, cyclopentanone) and six alkoxyalcohol (2-methoxyethanol, 2-ethoxyethanol, 2-propoxyethanol, 2-isopropoxyethanol, 2-butoxyethanol, 3-methoxy-1-butanol) mono-solvents at 298.15 K. Results from our experimental measurements, combined with the published solubility data, are used to calculate the solute descriptors of the carboxylic acid solute. The calculated descriptor values reported in the current study back-calculate the observed solubility data to within an approximate standard error of 0.05 log units.

Calculation of Abraham model solute descriptors for 2-naphthoxyacetic acid

Published solubility data for 4,5-dihydroxyanthraquinone-2-carboxylic acid dissolved in several organic solvents of varying polarity and hydrogen-bonding character are used to calculate the Abraham model solute descriptors. Calculated descriptor values suggest that 4,5-dihydroxyanthraquinone-2-carboxylic acid engages in intramolecular hydrogen formation between the two phenolic hydrogens and the proton acceptor sites (the lone electron pairs) on the neighboring quinone oxygen atom. Our study further shows that existing group contribution and machine learning methods provide rather poor estimates of the experimental-based solute descriptors of 4,5-dihydroxyanthraquinone-2-carboxylic acid, in part because the estimation methods to not account for the likely intramolecular hydrogen-bonds. The predictive aspect of the Abraham model is illustrated by predicting the solubility of 4,5-dihydroxyanthraquinone-2-carboxylic acid in 28 additional organic mono-solvents for which experimental data does not exist. 

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Rayssa Maluf de Souza

Papers

Abraham Solvation Parameter Model: Examination of Possible Intramolecular Hydrogen-Bonding Using Calculated Solute Descriptors

Comments on “Effect of alkyl chain length of 1-alkanols on solution behavior of bactericidal antibiotic in terms of thermo-acoustic parameters”

Comments on “Effect of alkyl chain length of 1-alkanols on solution behavior of bactericidal antibiotic in terms of thermo-acoustic parameters”