Synthesis, X-ray crystallographic, Hirshfeld, DFT study and interactions with TNFα receptors of chiral bisimines and diamines holding thiophene spacers

This paper outlines a facile synthesis of chiral bisimines R,R-(Thiophene-2,5-diyl)bis(N-(1-phenylethyl)methanimine) R,R-BI-1, S,S-(Thiophene-2,5-diyl)bis(N-(1-phenylethyl)methanimine) S,S-BI-2 and their reduced products R,R-(Thiophene-2,5-diyl)bis(N-(1-phenylethyl)methanamine) R,R-DA-1, S,S-(Thiophene-2,5-diyl)bis(N-(1-phenylethyl) methanamine) S,S-DA-2 holding thiophene spacers. The new derivatives were suitably characterized by microanalysis, standard spectroscopic techniques (H-1, C-13 NMR, FTIR, UV-visible absorption). Single crystal X-ray diffraction (SCXRD) method was used to study the supramolecular structures of R,R-BI-1 and S,S-BI-2, sustained primarily by CH & mldr;pi intermolecular contacts which are well supported by molecular electrostatic potential (MESP). Quantification of short contacts existing in the crystal packing of these molecules was accomplished by Hirshfeld surface and fingerprint plots calculations. The geometry of all the molecules has been optimized by using a density functional theory calculation and the theoretical data were compared well with the experimental outcomes. Further, the calculated HOMO-LUMO band gaps for R,R-BI-1, S,S-BI-2, R,R-DA-1 and S,S-DA-2 (4.05-5.30 eV) suggests their non-conducting nature. Moreover, virtual screening of these nitrogenous compounds has been performed by molecular docking study to propose their potentials as biologically relevant molecules.