Synthesis and Structural Characterization of Pyridine-2,6-dicarboxamide and Furan-2,5-dicarboxamide Derivatives

Molecules. 2022 Mar 10;27(6):1819. doi: 10.3390/molecules27061819.

Abstract

Derivatives based on pyridine-2-6- and furan-2,5-dicarboxamide scaffolds reveal numerous chemical properties and biological activities. This fact makes them an exciting research topic in supramolecular and coordination chemistry and in discovering new pharmacologically-active compounds. This work aimed to obtain a series of symmetrical pyridine-2-6- and furan-2,5-dicarboxamides through a condensation reaction of the appropriate acyl chlorides and aromatic amides. Successful syntheses were confirmed with NMR spectroscopy. We solved their crystal structures for seven compounds; two pyridine and five furan derivatives. Based on our crystallographic studies, we were able to indicate supramolecular features of the crystals under investigation. Additionally, Hirshfeld surface analysis allowed us to calculate a distribution of intermolecular contacts in the dicarboxamide crystals.

Keywords: Hirshfeld surface; crystal packing; crystallography; dicarboxamide; heterocyclic compounds; molecular structure.

MeSH terms

  • Amides / chemistry
  • Furans*
  • Magnetic Resonance Spectroscopy
  • Pyridines* / chemistry

Substances

  • Amides
  • Furans
  • Pyridines
  • pyridine-2,6-dicarboxamide