Synthesis, structural features, computational study along with molecular docking examination of organosulfur mercaptoacetic acid based compound

We carried out a thiylating reaction of p-nitroacetophenone with thioglycolic acid. The reaction was carried out in a benzene solution, with a molar ratio of the initial components of 1:4. 1,1-bis-(carboxymethylthio)-1-p-nitrophenylethane (CTNE). Structural features are evaluated via Fourier transform infrared (FT-IR) spectroscopy, 1H NMR and single crystal X-ray diffraction (XRD) analysis. Structure is composed of an organosulfur molecule and a water molecule. Organosulfur molecule adopted non-planar conformation supported via dihedral angle of 71.3 (4)degrees among carboxylic acid groups. Supramolecular organization is primarily supported via O-H & ctdot;O bonding. Further stability of the supramolecular organization is due to pi & ctdot;pi interactions with inter-centroid separation range from 3.85 to 4.01 & Aring;. Strong and weaker interactions are evaluated via Hirshfeld surface analysis which showed that H & ctdot;O contact has highest contribution in stability of the supramolecular organization. DFT calculations at the B3PW91/6-311 + + g (2d,2p) level was employed to optimize the molecular geometry and assess the electronic properties of the synthesized compound. Highest Occupied Molecular Orbital (HOMO)- Lowest Unoccupied Molecular Orbital (LUMO) energy gap (triangle E = 4.06 eV) of the synthesized compound indicates enhanced chemical reactivity and biological potential compared to precursor molecules. Furthermore, molecular docking studies demonstrated a promising binding affinity (-7.05 kcal/mol) toward VEGFR2, stabilized through hydrogen bonding and hydrophobic interactions, suggesting potential anticancer activity through angiogenesis inhibition.