Microwave assisted synthesis, X-ray crystallography and DFT calculations of selected aromatic thiosemicarbazones

Series of four benzaldehyde thiosemicarbazones has been synthesized under microwave irradiation and characterized structurally by means of infrared and NMR spectroscopies and mass spectrometry. Their crystal structures were determined by single crystal X-ray analysis followed by DFT calculations. Partial charges on the molecular surface and dipole moments of the structures were calculated. Crystal structures are stabilized by intramolecular hydrogen bonding and stacking interactions. Studied compounds are interesting as antiproliferative and antifungal agents acting through interactions with iron. Thus presented results may be useful in design new more active or specific structures.

► We have synthesized 4 thiosemicarbazones as possible anticancer agents.
► Their structures were studied by X-ray, DFT calculations, NMR, MS and IR.
► H-bonding, planarity distortion and electronic properties are discussed.
► These features may influence their biological activity.