Thermodynamics Research Center / ThermoML | Journal of Chemical and Engineering Data

ABSTRACT

The objective is to study the effect of solvent properties on solubility. In this work, the solubility of 2-chloronicotinic acid in methanol, ethanol, n-propanol, isopropanol, N,N-dimethylformamide (DMF), 1,4-dioxane, N-methyl pyrrolidone (NMP), ethyl acetate, acetone, water, acetonitrile and cyclohexane at temperatures ranging from 273.15 to 313.15 K was determined by isothermal saturation method under P =101.3 kPa. The maximum solubility value was obtained in pure NMP, and followed by in the DMF greater than ethyl acetate greater than acetone greater than 1,4-dioxane greater than n-propanol greater than isopropanol greater than ethanol greater than methanol greater than acetonitrile greater than cyclohexane greater than water. The obtained solubility data of 2-chloronicotinic acid in twelve pure solvents was correlated with the modified Apelblat equation and h equation. The maximum value of relative average deviations (RAD) and root-mean-square deviation (RMSD) are all no larger than 2.7210-2 and 35.5610-4, respectively, which indicates the experimental data is consistent well with calculated one. Furthermore, the properties of solvent including hydrogen bond acidity ( N w z hydrogen bond basicity ( O), dipolarity/polarizability ( a*) and Hildebrand solubility parameter ( ) were discussed. Compared with the polarity 2H O of the solvent, the hydrogen bond formed between the solvent and solute molecule is the main influencing factor. Understanding some physical properties of 2-chloronicotinic acid in commonly used organic solvents is important to drug crystallization.