A cocrystal is crystal made up of two or more components in a definite stoichiometric ratio. While structures of hundreds of binary cocrystals are known, few ternary cocrystals have been synthesized to date. The goal of this work was to determine the range of conditions under which three newly synthesized ternary cocrystals can form. Each of the three cocrystals contain acridine, 2-amino-4,6-dimethylpyrimidine and a carboxyphenol. Crystals were grown from sixteen different solvents and solvent mixtures using five different solution stoichiometries. The cocrystals formed in solution were analyzed using infrared spectroscopy to determine if a cocrystal was formed, and nuclear magnetic resonance to determine the stoichiometric ratio of components. After completing 120 experiments and analyzing 201 samples, it was clear that 6-hydroxy-2-naphthoic acid was able to form ternary cocrystals under a wide range of conditions, including from fourteen different solvents and from five different solution stoichiometries. <i>m</i>-Hydroxybenzoic acid and <i>trans</i>-ferulic acid, however, only formed ternary cocrystals under very specific sets of conditions.

Finding the sweet spot for ternary cocrystal formation

251st National Meeting (2016)

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