Crystal structure, DFT and HF calculations and radical scavenging activities of (E)-4,6-dibromo-3-methoxy-2-[(3-methoxyphenylimino)methyl]phenol

• The compound was synthesized and characterized using experimental and theoretical methods.
• Antioxidant properties were determined by using different methods.
• Homo-Lumo energy gap, molecular electrostatic potential map were performed.

In this study, (E)-4,6-dibromo-3-methoxy-2-[(3-methoxyphenylimino)methyl]phenol has been synthesized and characterized by using X-ray technique and FT-IR experimentally and using B3LYP/6-31G(d,p) and HF/6-31G(d,p) methods theoretically. The intermolecular and intramolecular interactions of the title compound have been determined according to X-ray results. The molecular geometry, vibrational frequencies of the title compound in the ground state have been calculated using the density functional B3LYP and HF method with the 6-31G(d,p) basis set and calculated bond parameters and vibrational frequencies values show good agreement with experimental values. Theoretical and experimental results show that tautomeric form of the structure is phenol-imine form. Besides HOMO–LUMO energy gap, molecular electrostatic potential map were performed at B3LYP/6-31G(d,p) level. It is worthy note of that, the free radical scavenging activities of the title compound were assessed using DPPH, DMPD+, and ABTS+ assays. The obtained results show that the title compound has effective DPPH (SC50 2.61 ± 0.09 μg/mL), DMPD+ (SC50 2.82 ± 0.14 μg/mL), and ABTS+ (SC50 4.91 ± 0.18 μg/mL) radical scavenging activities when compared with standard antioxidants (BHA, rutin, and trolox).

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