We have prepared a series of cocrystal salts from the crystallization of benzene polycarboxylic acids (terephthalic, isophthalic, phthalic, trimesic, and pyromellitic acids) with methylimidazole. All compounds have been characterized by single-crystal X-ray diffraction and FTIR spectroscopy. The resulting benzene carboxylic acids vary in their degree of ionization, with some forming hydrogen-bonded cocrystals (terephthalic acid) and others partially deprotonating to form imidazolium salts with hydrogen-bonded networks. For most compounds the salt formation can be related to differences in p<i>K</i><sub>a</sub> values for the acid/base pair.

Cocrystal versus salt formation in a series of benzene polycarboxylic acids crystallized with methylimidazole

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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