Development of Abraham model correlations for solvation characteristics of secondary and branched alcohols

Abstract

Data have been compiled from the published literature on the partition coefficients of solutes and vapors into the anhydrous secondary and branched alcohols (2-propanol, 2-butanol, 2-methyl-1-propanol, 2-methyl-2-propanol and 3-methyl-1-butanol) from both water and from the gas phase. The logarithms of the water-to-alcohol partition coefficients (log P) and gas-toalcohol partition coefficients (log K) were correlated with the Abraham solvation parameter model. The derived correlations described the observed log P and log K values to within average standard deviations of 0.14 and 0.13 log units, respectively. The predictive abilities of the each correlation were assessed by dividing databases into a separate training set and test set.

IUPAC-NIST Solubility Data Series. 102. Solubility of Nonsteroidal Anti-inflammatory Drugs (NSAIDs) in Neat Organic Solvents and Organic Solvent Mixtures

“…(10) and (11) described the molar solubility of benzil in 24 organic solvents to within overall standard deviations of 0.124 and 0.109 log 10 units, respectively. 35 Standard deviations for aspirin dissolved in 13 alcohols, 4 ethers, and ethyl ethanoate were 0.123 and 0.138 log 10 units. 25 Benzil 48 and aspirin 25 exhibited solubilities exceeding 1 molar in several of the organic solvents studied.…”

“…(10) and (11) are obtained by multiple linear regression analysis of experimental partition coefficient data and solubility ratios for a specific biphasic system. To date, Abraham model correlations have been developed for predicting the solubility of crystalline nonelectrolytes in more than 70 different organic solvents, [28][29][30][31][32][33][34][35] for predicting the water-toorganic solvent and gas-to-organic solvent partition coefficient for more than 70 different biphasic systems, [28][29][30][31][32][33][34][35][36][37] and for predicting the partition coefficients of organic vapors and gaseous solutes into aqueous micellar solvent media, 38,39 into humic acid, 40 and into various body tissues and fluids. [41][42][43][44][45][46][47] Each of the aforementioned predictions requires a priori knowledge of the compound's solute descriptors as input parameters.…”

Enthalpy of solvation correlations for organic solutes and gases dissolved in 2-propanol, 2-butanol, 2-methyl-1-propanol and ethanol

“…Such transfer processes form the basis of chemical separations involving gas-liquid chromatography, absorption of gases onto solid-phase microextraction absorbents, atmospheric transport and redistribution of volatile organic pollutants in the environment, and chemical purifications involving gas stripping methods. To date, we have developed Abraham model correlations for describing the logarithm of the gas-to-organic solvent partition coefficients, log K, [1][2][3][4][5][6][7] log K = c + e·E + s·S + a·A + b·B + l·L (1) of organic vapors and gases into more than 70 different organic solvents of varying polarity and Δ Solv H o = c + e·E + s·S + a·A + b·B + v·V (3) of organic vapors and gases into water [8], and into four alkanes (hexane [9], heptane [10], hexadecane [10] and cyclohexane [10]), into two aromatic hydrocarbons (benzene [10] and toluene [11]), into five alcohols (methanol [12], ethanol [12], 1-butanol [12], 1-octanol [8] and tert-butanol [13]), into three chloroalkanes (chloroform [14], carbon tetrachloride [11] and 1,2-dichloroethane [14]), and into seven other organic solvents (dibutyl ether [15], ethyl acetate [15], acetone [16], dimethyl sulfoxide [17], acetonitrile [16], propylene carbonate [17] and N,Ndimethylformamide [13] …”

Development of correlations for describing solute transfer into acyclic alcohol solvents based on the Abraham model and fragment-specific equation coefficients

“…The proposed method is illustrated using 1879 experimental log P and 1880 experimental log K values for organic solutes and gases dissolved in anhydrous linear, secondary, tertiary and methyl-branched alcohols. For anhydrous alcohols, the log P values refer to a hypothetical partition process as discussed in detail elsewhere [24][25][26][27][28][29][30]. Even though hypothetical, the derived log P correlations are still quite useful in that predicted log P values can be used to estimate the solute's infinite dilution activity coefficient or the solute's molar solubility in the anhydrous (dry) alcohol solvent.…”