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

Alasalvar C., Soylu M. S., Guder A., Albayrak C., APAYDIN G., Dilek N.

SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, vol.125, pp.319-327, 2014 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 125
  • Publication Date: 2014
  • Doi Number: 10.1016/j.saa.2014.01.104
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.319-327
  • Keywords: Schiff base, Crystal structure, DFT and HF methods, Optimized geometry, Radical scavenging activities, DENSITY-FUNCTIONAL THEORY, ANTIOXIDANT ACTIVITY, SCHIFF-BASES, ABSOLUTE ELECTRONEGATIVITY, FT-IR, DERIVATIVES, HARDNESS, RAMAN, UV
  • Karadeniz Technical University Affiliated: Yes


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 center dot, DMPD center dot +/-, and ABTS(center dot +/-) assays. The obtained results show that the title compound has effective DPPH center dot (SC50 2.61 +/- 0.09 mu g/mL), DMPD center dot +/- (SC50 2.82 +/- 0.14 mu g/mL), and ABTS(center dot +/-) (SC50 4.91 +/- 0.18 mu g/mL) radical scavenging activities when compared with standard antioxidants (BHA, rutin, and trolox). (C) 2014 Elsevier B.V. All rights reserved.