Quantum-chemical, spectroscopic and X-ray diffraction studies of (E)-2-[(2-Bromophenyl)iminomethyl]-4-trifluoromethoxyphenol

The Schiff base compound (E)-2-[(2-Bromophenyl)iminomethyl]-4-trifluoromethoxyphenol has been synthesised and characterised by IR, UV–vis, and X-ray single-crystal determination. The molecular geometry from X-ray determination of the title compound in the ground state has been compared using the Hartree–Fock (HF) and density functional theory (DFT) with the 6–311++G(d,p) basis set. The calculated results show that the DFT and HF can well reproduce the structure of the title compound. Using the TD-DFT and TD-HF methods, electronic absorption spectra of the title compound have been predicted and good agreement with the TD-DFT method and the experimental determination was found. The predicted nonlinear optical properties of the title compound are much greater than those of urea. In addition, DFT calculations of the title compound, molecular electrostatic potential (MEP), natural bond orbital (NBO), and thermodynamic properties were performed at B3LYP/6–311++G(d,p) level of theory.

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► The X-ray, IR and UV–vis spectral data for the title compound show that the compound exists in the enol-imine tautomeric form.
► The TD-DFT calculations lead to a very closer agreement with the experimental absorption spectra both in gas phase and solvent media.
► The predicted nonlinear optical (NLO) properties of the title compound are much greater than ones of urea.
► The NBO analysis revealed that the n(N1) → σ(O1–H1) interaction gives the strongest stabilization to the system.
► The title compound is a good candidate of nonlinear optical material.