The Co-Crystallization of 4-Halophenylboronic Acid with Aciclovir, Caffeine, Nitrofurazone, Theophylline, and Proline in Function of Weak Interactions

Co-crystallization experiments of 4-halophenylboronic acid with several pharmaceutical compounds (including aciclovir, caffeine, nitrofurazone, and proline) produced several new molecular complexes. The experiments involved varying the solvent and the molar ratio of boronic acid to a pharmaceutical compound (e.g., 1:1, 2:1, 1:2). The screening process for new crystal phases revealed that the formation of the different molecular complexes was strongly influenced by the molar ratio and the presence or absence of water in the solvent. The new molecular crystals were characterized through single crystal X-ray diffraction and differential scanning calorimetry (DSC) analyses. The single crystal analyses of the molecular complexes revealed an unexpected variety in the hydrogen bonding network interactions that can be produced by the –B(OH)2 motif.