Crystal structure, spectroscopic and theoretical studies on two Schiff base compounds of 2,6-dichlorobenzylidene-2,4-dichloroaniline and 2,4-dichlorobenzylidene-2,4-dichloroaniline

• 2,6-dichlorobenzylidene-2,4-dichloroaniline and 2,4-dichlorobenzylidene-2,4-dichloroaniline are investigated.
• The synthesized compounds were theoretically and experimentally characterized using X-ray, IR, and 1H NMR.
• The theoretical calculations were carried out using B3LYP method at 6-31G∗ and STO-3G basis sets.
• The calculated the electronic properties and atomic charges were presented.

The crystal structures of two Schiff base compounds, 2,6-dichlorobenzylidene-2,4-dichloroaniline (1) and 2,4-dichlorobenzylidene-2,4-dichloroaniline (2) have been determined from single-crystal X-ray diffraction and characterized by FT-IR and 1H NMR spectroscopy. The electronic structures of compounds 1 and 2 in the gas phase were computed by the density functional theory (DFT) method. The obtained theoretical results were supported by the crystallographic data. In addition, theoretical configurations of the title compounds were relaxed and studied in terms of the combined analysis of HOMO–LUMO energy gap, total density of states (DOS), molecular electrostatic potential (MEP), NMR spectra and harmonic vibrational frequencies.

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