title: Structure-property relationships in halogenbenzoic acids: Thermodynamics of sublimation, fusion, vaporization and solubility.
abstract: Temperature dependences of vapor pressures for 2-, 3-, and 4-bromobenzoic acid, as well as for five isomeric bromo-methylbenzoic acids were studied by the transpiration method. Melting temperatures and enthalpies of fusion for all isomeric bromo-methylbenzoic acids and 4-bromobenzoic acid were measured with a DSC. The molar enthalpies of sublimation and vaporization were derived. These data together with results available in the literature were collected and checked for internal consistency using a group-additivity procedure and results from X-ray structural diffraction studies. Specific (hydrogen bonding) interactions in the liquid and in the crystal phase of halogenbenzoic acids were quantified based on experimental values of vaporization and sublimation enthalpies. Structure-property correlations of solubilities of halogenobenzoic acids with sublimation pressures and sublimation enthalpies were developed and solubilities of bromo-benzoic acids were estimated. These new results resolve much of the ambiguity in the available thermochemical and solubility data on bromobenzoic acids. The approach based on structure property correlations can be applied for the assessment of water solubility of sparingly soluble drugs.
authors.affiliation: Nikolaev Institute of Inorganic Chemistry of Siberian Branch of Russian Academy of Sciences, 630090 Novosibirsk, Russia.
authors.forename: Kseniya V
authors.initials: KV
authors.lastname: Zherikova
authors.affiliation: Chemical Department, Samara State Technical University, 443100 Samara, Russia.
authors.forename: Aleksey A
authors.initials: AA
authors.lastname: Svetlov
authors.affiliation: Nikolaev Institute of Inorganic Chemistry of Siberian Branch of Russian Academy of Sciences, 630090 Novosibirsk, Russia; Novosibirsk State University, 630090 Novosibirsk, Russia.
authors.forename: Natalia V
authors.initials: NV
authors.lastname: Kuratieva
authors.affiliation: Department of Physical Chemistry, University of Rostock, D-18059 Rostock, Germany; Department of Physical Chemistry, Kazan Federal University, Kremlevskaya str. 18, 420008 Kazan, Russia. Electronic address: sergey.verevkin@uni-rostock.de.
authors.forename: Sergey P
authors.initials: SP
authors.lastname: Verevkin
keywords: Enthalpy of sublimation; Group-additivity; Hydrogen bonding; Solubility; Vapor pressure; X-ray diffraction