10.6084/m9.figshare.8396942.v2 Jesus Daniel Loya Jesus Daniel Loya Selena J. Li Selena J. Li Daniel K. Unruh Daniel K. Unruh Kristin M. Hutchins Kristin M. Hutchins Application of the pK<sub>a</sub> rule to synthesize salts of bezafibrate Taylor & Francis Group 2019 Pharmaceutical salt co-crystal pKa rule hydrogen bonding 2019-09-03 07:34:29 Journal contribution https://tandf.figshare.com/articles/journal_contribution/Application_of_the_pK_sub_a_sub_rule_to_synthesize_salts_of_bezafibrate/8396942 <p>Co-crystallization frequently employs forces such as hydrogen bonds, halogen bonds, and π-π stacking to assemble molecules in a multi-component crystal. In an effort to increase the strength of the intermolecular interaction between the anti-cholesterol drug bezafibrate (<b>BEZA</b>), a wastewater contaminant, and hydrogen-bond-acceptor molecules, we modified the pK<sub>a</sub> values of the acceptors. Here, we describe the first series of salts incorporating <b>BEZA</b> and achieve a variety of supramolecular architectures including discrete assemblies, 1D chains, tapes, and 2D sheets. We discuss exceptions to the pK<sub>a</sub> rule, and demonstrate that the presence of hydrogen-bond-donor atoms on the acceptor molecule supports salt formation.</p>