Synthesis, crystal structure and computational studies of a new Schiff base compound: (E)-4-bromo-2-ethoxy-6-{[(2-methoxyphenyl)imino]methyl}phenol

Abstract

The title compound, C16H16BrNO3, which shows enol–imine tautomerism, crystallizes in the monoclinic P21/c space group. All non-H atoms of the molecule are nearly coplanar, with a maximum deviation of 0.274 (3) Å. In the crystal, molecules are held together by weak C—H...O, π–π and C—H...π interactions. The E/Z isomerism and enol/keto tautomerism energy barriers of the compound have been calculated by relaxed potential energy surface scan calculations with DFT methods. To observe the changes in the aromatic ring, HOMA aromaticity indexes were calculated during the scan process. Total energy and HOMA change curves were obtained to visualize results of the scan calculations.

Keywords

• Schiff bas
• crystal structure
• DFT
• 5-bromo-3-ethoxy-2-hydroxybenzaldehyde
• 2-methoxyaniline