Application of the pKa rule to synthesize salts of bezafibrate

Jesus Daniel Loya, Selena J. Li, Daniel K. Unruh, Kristin M. Hutchins

Research output: Contribution to journalArticle

Abstract

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 (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.

Original languageEnglish
Pages (from-to)558-564
Number of pages7
JournalSupramolecular Chemistry
Volume31
Issue number8
DOIs
StatePublished - Aug 3 2019

Keywords

  • Pharmaceutical
  • co-crystal
  • hydrogen bonding
  • pK rule
  • salt

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