Development of Abraham model expressions for predicting the enthalpies of solvation of solutes dissolved in acetic acid

ABSTRACT Experimental data have been compiled from the published chemical and engineering literature on the enthalpies of solvation for 92 different inorganic gases and organic vapours in acetic acid. The compiled data are used to derive mathematical correlations based on the Abraham solvation parameter model. The derived expressions describe the experimental solvation enthalpies in acetic acid to within a standard deviation (SD) of 2.2 kJ mol−1. Principal Component Analysis (PCA) on the five equation coefficients from a derived Abraham model correlation shows that acetic acid does not resemble hydroxylic solvents in terms of enthalpic interactions, but is more akin to moderately polar solvents such as ethyl acetate or acetone.

[1]  M. Abraham,et al.  Abraham model enthalpy of solvation correlations for solutes dissolved in dimethyl carbonate and diethyl carbonate , 2015 .

[2]  M. Abraham,et al.  Abraham model enthalpy of solvation correlations for solutes dissolved in 1-alkanol solvents (C4–C6) , 2015 .

[3]  M. Abraham,et al.  Abraham model correlations for describing solute transfer into diisopropyl ether , 2015 .

[4]  M. Abraham,et al.  Abraham model correlations for solute transfer into tributyl phosphate from both water and the gas phase , 2015 .

[5]  A. Toikka,et al.  Excess molar enthalpies for binary mixtures of n -propanol, acetic acid, and n -propyl acetate at 313.15K and atmospheric pressure , 2014 .

[6]  M. Abraham,et al.  Examination of hydrogen-bonding interactions between dissolved solutes and alkylbenzene solvents based on Abraham model correlations derived from measured enthalpies of solvation , 2014 .

[7]  H. Hao,et al.  An odd–even effect on solubility of dicarboxylic acids in organic solvents , 2014 .

[8]  C. Poole,et al.  Determination of descriptors for polycyclic aromatic hydrocarbons and related compounds by chromatographic methods and liquid-liquid partition in totally organic biphasic systems. , 2014, Journal of chromatography. A.

[9]  M. Abraham,et al.  Descriptors for the Prediction of Partition Coefficients of 8-Hydroxyquinoline and its Derivatives , 2014 .

[10]  Yonghong Hu,et al.  Measurement and correlation of the solubility of 4-methylbenzoic acid in (methanol + acetic acid) binary solvent mixtures , 2014 .

[11]  M. Abraham,et al.  Enthalpy of solvation correlations for organic solutes and gases dissolved in dichloromethane and 1,4-dioxane , 2013, Structural Chemistry.

[12]  M. Abraham,et al.  Descriptors for the Prediction of Partition Coefficients and Solubilities of Organophosphorus Compounds , 2013, Separation science and technology.

[13]  C. Poole,et al.  Totally organic biphasic solvent systems for extraction and descriptor determinations. , 2013, Journal of Separation Science.

[14]  L. Lepori,et al.  Excess enthalpies of mixtures of mono-carboxylic acid with dibutylether , 2012, Journal of Thermal Analysis and Calorimetry.

[15]  M. Abraham,et al.  Enthalpy of solvation correlations for organic solutes and gases dissolved in 2-propanol, 2-butanol, 2-methyl-1-propanol and ethanol , 2011 .

[16]  M. Abraham,et al.  Enthalpy of Solvation Correlations for Organic Solutes and Gases Dissolved in 1-Propanol and Tetrahydrofuran , 2011 .

[17]  S. Imberti,et al.  Formic and acetic acid aggregation in the liquid state , 2010, Journal of physics. Condensed matter : an Institute of Physics journal.

[18]  James S. Chickos,et al.  Phase Transition Enthalpy Measurements of Organic and Organometallic Compounds. Sublimation, Vaporization and Fusion Enthalpies From 1880 to 2010 , 2010 .

[19]  Michael H Abraham,et al.  Prediction of solubility of drugs and other compounds in organic solvents. , 2010, Journal of pharmaceutical sciences.

[20]  M. Abraham,et al.  Development of Abraham model correlations for solvation characteristics of secondary and branched alcohols , 2010 .

[21]  M. Abraham,et al.  Development of Abraham model correlations for solvation characteristics of linear alcohols , 2009 .

[22]  M. Abraham,et al.  Partition of compounds from water and from air into amides. , 2009, New journal of chemistry = Nouveau journal de chimie.

[23]  A. Leo,et al.  Correlation and prediction of solute transfer to chloroalkanes from both water and the gas phase , 2009 .

[24]  M. Abraham,et al.  Enthalpy of solvation correlations for organic solutes and gases dissolved in acetonitrile and acetone , 2009 .

[25]  M. Abraham,et al.  Enthalpy of solvation correlations for organic solutes and gases dissolved in N,N-dimethylformamide and tert-butanol , 2009 .

[26]  M. Abraham,et al.  Correlation and Prediction of Partition Coefficients From the Gas Phase and from Water to Alkan-1-ols , 2008 .

[27]  M. Abraham,et al.  Enthalpy of solvation correlations for gaseous solutes dissolved in dibutyl ether and ethyl acetate , 2008 .

[28]  M. Abraham,et al.  Enthalpy of Solvation Correlations For Gaseous Solutes Dissolved in Linear Alkanes (C5C16) Based on the Abraham Model , 2008 .

[29]  Michael Clark,et al.  Enthalpy of Solvation Correlations for Gaseous Solutes Dissolved in Water and in 1-Octanol Based on the Abraham Model , 2007, J. Chem. Inf. Model..

[30]  J. Gmehling,et al.  Measurement of the thermodynamic properties for the reactive system ethylene glycol–acetic acid , 2007 .

[31]  M. Abraham,et al.  Enthalpy of Solvation Correlations for Gaseous Solutes Dissolved in Chloroform and 1,2-dichloroethane Based on the Abraham Model , 2007 .

[32]  H. Noguchi,et al.  Liquid structure of acetic acid-water and trifluoroacetic acid-water mixtures studied by large-angle X-ray scattering and NMR. , 2007, The journal of physical chemistry. B.

[33]  M. Abraham,et al.  Enthalpy of Solvation Correlations for Gaseous Solutes Dissolved in Dimethyl Sulfoxide and Propylene Carbonate Based on the Abraham Model , 2007 .

[34]  Christina Mintz,et al.  Enthalpy of Solvation Correlations for Gaseous Solutes Dissolved in Toluene and Carbon Tetrachloride Based on the Abraham Model , 2007 .

[35]  M. Abraham,et al.  Enthalpy of Solvation Correlations for Gaseous Solutes Dissolved in Benzene and in Alkane Solvents Based on the Abraham Model , 2007 .

[36]  Å. Rasmuson,et al.  Solubility and Melting Properties of Salicylic Acid , 2006 .

[37]  D. Rogers Heats of Hydrogenation , 2006 .

[38]  Adam Ibrahim,et al.  Determination of sets of solute descriptors from chromatographic measurements. , 2004, Journal of chromatography. A.

[39]  T. Letcher,et al.  Thermodynamic excess properties for binary mixtures of (benzonitrile + a carboxylic acid) at T = 298.15 K , 2002 .

[40]  T. Letcher,et al.  Thermodynamic excess properties for binary mixtures of (butanenitrile + a carboxylic acid) atT = 298.15 K , 2001 .

[41]  Ma Peisheng Determination and Correlation for Solubility of Aromatic Acids in Solvents , 2001 .

[42]  William E. Acree,et al.  Partition of solutes from the gas phase and from water to wet and dry di-n-butyl ether: a linear free energy relationship analysis , 2001 .

[43]  马沛生,et al.  Determination and Correlation for Solubility of Aromatic Acids in Solvents , 2001 .

[44]  T. Nakabayashi,et al.  Liquid Structure of Acetic Acid Studied by Raman Spectroscopy and Ab Initio Molecular Orbital Calculations , 1999 .

[45]  J. Grolier,et al.  Excess molar enthalpies of (an alkanoic acid + n-heptane, or cyclohexane, or benzene) atT = 298.15 K☆ , 1999 .

[46]  R. Francesconi,et al.  Excess molar enthalpies of binary mixtures containing acetic or propionic acid+eight ethyl alkanoates at 298.15 K , 1998 .

[47]  S. Ottani,et al.  Excess molar enthalpies and excess molar volumes of dialkyl carbonates + acetic or propionic acid at 298.15 K , 1997 .

[48]  V. Mochalin,et al.  Solubility of Hydrocarbons in Acetic Acid , 1997 .

[49]  Michael H. Abraham,et al.  Scales of solute hydrogen-bonding: their construction and application to physicochemical and biochemical processes , 2010 .

[50]  A. Krishnaiah,et al.  Thermodynamics of binary mixtures containing cyclic ethers , 1992 .

[51]  R. Lichtenthaler,et al.  Excess enthalpy of the system butyl acetate + butan-1-ol + acetic acid + water at 313 K and ambient pressure , 1991 .

[52]  R. C. Katyal,et al.  Enthalpies of mixing and viscosities of binary systems acetic acid with o-, m-, p-xylene at 298-15 K , 1991 .

[53]  J. Catalán,et al.  Toward a solvent basicity scale: the calorimetry of the pyrrole probe , 1990 .

[54]  Jun-Ning Zhao,et al.  Excess molar enthalpies of (an alkanol + a carboxylic acid) at 298.15 K measured with a Picker calorimeter , 1989 .

[55]  R. Francesconi,et al.  Liquid-phase enthalpy of mixing for binary mixtures with associated components. The mixture of 1,3-dioxolane-acetic acid , 1989 .

[56]  Peter W. Carr,et al.  Solubility of xenon in 45 organic solvents including cycloalkanes, acids, and alkanals: Experiment and theory , 1989 .

[57]  R. L. Rowley,et al.  Handbook of Heats of Mixing, Supplementary Volume , 1988 .

[58]  Michael H. Abraham,et al.  Substitution at saturated carbon. Part 26. A complete analysis of solvent effects on initial states and transition states for the solvolysis of the t-butyl halides in terms of G, H, and S using the unified method , 1988 .

[59]  Abul Hussam,et al.  Experimental reexamination of selected partition coefficients from Rohrschneider's data set , 1987 .

[60]  D. Rogers,et al.  Microcalorimetric determination of enthalpies of solution of methyl alkanes in glacial acetic acid , 1986 .

[61]  Raghunath V. Chaudhari,et al.  Solubility of carbon monoxide in aqueous mixtures of methanol, acetic acid, ethanol and propionic acid , 1985 .

[62]  D. Rogers,et al.  A microcomputer-controlled microcalorimeter calibration circuit , 1985 .

[63]  A. Beerbower,et al.  Expanded solubility parameter approach. I: Naphthalene and benzoic acid in individual solvents. , 1984, Journal of pharmaceutical sciences.

[64]  J. Grolier,et al.  Thermodynamics of binary mixtures containing cyclic ethers 5. Excess enthalpies of 1,3-dioxolane +, and 1,4-dioxane + alkanoic acid (HCO2H to C7H15CO2H) , 1982 .

[65]  L. A. Peacock,et al.  Gaseous heats of hydrogenation of some cyclic and open chain alkenes , 1979 .

[66]  H. A. Skinner,et al.  Heats of hydrogenation. Part 3 , 1959 .