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>