Highly Functionalized N-1 Arylmethylidene]tetrahydro-4(1H) 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 Xray crystallographic studies. The Hirshfeld analysis reveals that the molecular packing of 5a is mainly controlled by N center dot center dot center dot H (4.9%), C center dot center dot center dot H (30.6%) and H center dot center dot center dot H (52.4%) contacts whereas the molecules are packed by strong F center dot center dot center dot H (16.8-16.9 %), N center dot center dot center dot H (5.4%) and O center dot center dot center dot H (5.2-5.4%) as well as weak C center dot center dot center dot O (3.9-4.5%), H center dot center dot center dot H (39.7-39.9%) and C center dot center dot center dot 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. (C) 2020 Elsevier B.V. All rights reserved.