Molecular structure, quantum mechanical calculation and radical scavenging activities of (E)-4,6-dibromo-2-[(3,5-dimethylphenylimino)methyl]-3-methoxyphenol and (E)-4,6-dibromo-2-[(2,6-dimethylphenylimino)methyl]-3-methoxyphenol compounds

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

SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, vol.130, pp.357-366, 2014 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 130
  • Publication Date: 2014
  • Doi Number: 10.1016/j.saa.2014.03.069
  • Journal Name: SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.357-366
  • Keywords: Schiff base, Crystal structure, DFT method, Radical scavenging activities, DENSITY-FUNCTIONAL THEORY, ANTIOXIDANT PROPERTIES, MICRO-RAMAN, SOLID-STATE, HARDNESS, ENERGY, IR
  • Karadeniz Technical University Affiliated: Yes

Abstract

In this study, (E)-4,6-dibromo-2-[(3,5-dimethylphenylimino)methyl]-3-methoxyphenol and (E)-4,6-dibromo-2-[(2,6-dimethylphenylimino)methyl]-3-methoxyphenol compounds have been.synthesized and characterized by using X-ray crystallographic method, FT-IR and Density functional method. The molecular geometry, vibrational frequencies of, the title compounds in the ground state have been calculated by using B3LYP with the 6-31G(d,p) basis set. The tautomeric form of the compounds has been demonstrated by using single crystal X-ray method, FT-IR spectrometer and DFT method. In addition, HOMO-LUMO energy gap, molecular electrostatic potential map and NBO analysis of the compounds are performed at B3LYP/6-31G(d,p) level. It may be remarked that the free radical scavenging activities of the title compounds were assessed using DPPH., DMPD.+, and ABTS(.+) assays. The obtained results show that especially compound 2 has effective DPPH. (SC50 1.52 +/- 0.14 mu g/mL), DMPD.+ (SC50 1.22 +/- 0.21 mu g/mL), and ABTS' (SC50 3.32 +/- 0.17 mu g/mL) scavenging activities compared with standards (BHA, rutin, and trolox). (C) 2014 Elsevier B.V. All rights reserved.