Application of the pKa rule to synthesize salts of bezafibrate |
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Authors: | Jesus Daniel Loya Selena J. Li Daniel K. Unruh |
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Affiliation: | 1. Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX, USAhttps://orcid.org/0000-0002-9006-9671;2. Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX, USA;3. Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX, USAhttps://orcid.org/0000-0002-2594-5786 |
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Abstract: | ABSTRACTCo-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 (BEZA), a wastewater contaminant, and hydrogen-bond-acceptor molecules, we modified the pKa values of the acceptors. Here, we describe the first series of salts incorporating BEZA and achieve a variety of supramolecular architectures including discrete assemblies, 1D chains, tapes, and 2D sheets. We discuss exceptions to the pKa rule, and demonstrate that the presence of hydrogen-bond-donor atoms on the acceptor molecule supports salt formation. |
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Keywords: | Pharmaceutical salt co-crystal pKa rule hydrogen bonding |
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