Abstract
The solubilities of phenylboronic acid, its pinacol ester and azaester in organic solvents (chloroform, 3-pentanone, acetone, dipropyl ether and methylcyclohexane) have been determined experimentally by a dynamic method, in which the disappearance of turbidity was determined by measuring of light intensity using a luminance probe. Phenylboronic acid has high solubility in ether and ketones, moderate in chloroform and very low in hydrocarbon. Pinacol ester and azaester show better solubility than the parent acid in all tested solvents. For pinacol ester differences between particular solvents are small, while for azaester the differences are significant. For both esters the highest solubility is observed in chloroform and the lowest in the hydrocarbon. The results have been correlated by the Wilson, NRTL and Redlich–Kister equations. For the phenylboronic acid better correlation of the data is obtained by polynomials in comparison with the above equations. It is connected with additional acid-anhydride equilibrium in the system. The influence of polarity of the solvents on the solubility is discussed.
Highlights
Arylboronic acids and their derivatives are an important group of compounds due to their broad applications in organic synthesis, catalysis, supramolecular chemistry, and materials engineering [1,2,3,4]
The best solubility of phenylboronic acid is observed in dipropyl ether
The solubility in chloroform is relatively good, and the slope of this curve suggests the possibility of using this solvent for the crystallization of boronic acids
Summary
Arylboronic acids and their derivatives are an important group of compounds due to their broad applications in organic synthesis, catalysis, supramolecular chemistry, and materials engineering [1,2,3,4]. Journal of Solution Chemistry (2020) 49:814–824 as biologically active compounds [8]. Such wide applications require recognition of the physicochemical properties of these compounds. An important issue is the description of phase equilibria, including solubility in water and organic solvents. Knowledge of these data allows correct selection of the solvent for a particular reaction or for purification of the products by crystallization. They are important for biological tests and formulation of biologically active compounds
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