Highly functionalized N-1-(2-pyridinylmethyl)-3,5-bis[(E)-arylmethylidene]tetrahydro-4(1H)-pyridinones: Synthesis, characterization, crystal structure and DFT studies

Abstract Highly functionalized N-1-(2-pyridinylmethyl)-3,5-bis[(E)-methoxy/fluorophenylmethylidene]-tetrahydro-4(1H)-pyridinones (5a and 5b) have been synthesized in good yields. The molecular structure of the synthesized compounds was elucidated by NMR spectroscopy and further confirmed by single crystal X-ray crystallographic studies. The Hirshfeld analysis reveals that the molecular packing of 5a is mainly controlled by N...H (4.9%), C...H (30.6%) and H...H (52.4%) contacts whereas the molecules are packed by strong F...H (16.8-16.9 %), N...H (5.4%) and O...H (5.2-5.4%) as well as weak C...C (3.9-4.5%), H...H (39.7-39.9%) and C...H (24.8-25.8%) contacts in 5b. DFT calculations are used in order to predict the electronic properties of studied compounds. The NMR data obtained experimentally correlated well with the calculated findings.