Structural and computational analysis, spectroscopic and electrochemical elucidation of a Schiff base

Schiff base 4-(((3-(trifluoromethyl)phenyl)imino)methyl)phenol (TPP) was successfully synthesized and characterized by FT-IR, NMR and SC-XRD. Crystal analysis pointed up the presence of two crystallographically independent molecules in an asymmetric unit that are linked with each other through O-H center dot center dot center dot N and comparatively weak C-H center dot center dot center dot O bonding to form an infinite one-dimensional chain of horizontal ellipsis ABAB horizontal ellipsis sequence. In addition to H-bonding, crystal packing is further stabilized by weak C-F center dot center dot center dot Cg and pi-pi stacking interactions. Hirshfeld surface analysis revealed that the most significant contribution to packing is from H-F/F-H interatomic contact with percentage contributions of 27.8% and 27.4% for molecules A and B, respectively. Quantum mechanical approach was used for comparison analysis between experimental and calculated parameters. Photometric behavior of TPP was studied in a wide pH range. Furthermore, redox mechanism was also suggested for TPP based on detailed electrochemical characterization. This effort just provides preliminary data to explore some structural and computational aspects of TPP.