Synthesis, characterization, crystal structure and theoretical studies of N-(2,4-dichlorobenzylidene)-3-methylbenzenamine

Abstract

N-(2,4-dichlorobenzylidene)-3-methylbenzenamine ( L6 ) was synthesized as single crystal and characterized by FT-IR, Raman, 1 H NMR, 13 C NMR and UV-VIS spectroscopy. The thermal stability of the title compound was also studied by thermogravimetric analysis (TGA) and differential thermal analysis (DTA) analyses. The optimized geometric parameters, conformational analysis, normal mode frequencies and corresponding vibrational assignments of L6 was theoretically examined by means of density functional theory (DFT) method using the Becke-3-Lee-Yang-Parr (B3LYP) exchange-correlation functional and the 6-311G++(d, p) basis sets. The DFT based nuclear magnetic resonance (NMR) calculations was also performed to use for assigning the 1 H and 13 C NMR chemical shifts of L6 . Reliable vibrational assignments were investigated by the potential energy distribution analysis and the highest occupied and the lowest unoccupied molecular orbitals (HOMO and LUMO) of L6 was predicted. A good consistency was obtained between the theoretically predicted structural parameters, vibrational frequencies and those obtained experimentally.