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) exchangecorrelation functional and the 6-311G++(d, p) basis sets. The DFT based nuclear magnetic resonance (NMR) calculations were also performed to be used 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 were obtained between the theoretically predicted structural parameters, vibrational frequencies and those obtained experimentally.

Synthesis, Characterization and Theoretical Calculation of 4-(((1h-Imidazol-2-Yl)methylene)amino)phenol

“…1H-imidazole-2-carbaldehyde (1 mmol) was dissolved in absolute ethanol (50 mL) and the temperature was raised to 60°C and stirring was continued at this temperature until the aldehyde dissolved [5]. Then 4-aminophenol (1 mmol) was added to the mixture.…”

“…The first preparation of Schiff bases was reported in 1864 by H. Schiff [4]. Since then, various methods for the synthesis of Schiff bases have been described [5]. The simple imine derivatives are generally synthesized from the condensation of aldehyde and primary amines.…”