title: Crystal structure, DFT and HF calculations and radical scavenging activities of (E)-4,6-dibromo-3-methoxy-2-[(3-methoxyphenylimino)methyl]phenol.
abstract: 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).
authors.affiliation: Giresun University, Faculty of Art and Science, Department of Physics, 28100 Giresun, Turkey. Electronic address: canalasalvar@hotmail.com.
authors.forename: Can
authors.initials: C
authors.lastname: Alaşalvar
authors.affiliation: Giresun University, Faculty of Art and Science, Department of Physics, 28100 Giresun, Turkey.
authors.forename: Mustafa Serkan
authors.initials: MS
authors.lastname: Soylu
authors.affiliation: Giresun University, Vocational High School of Health Services, Department of Medical Services and Techniques, 28100 Giresun, Turkey.
authors.forename: Aytaç
authors.initials: A
authors.lastname: Güder
authors.affiliation: Sinop University, Faculty of Arts and Sciences, Department of Chemistry, 57000 Sinop, Turkey.
authors.forename: Çiğdem
authors.initials: Ç
authors.lastname: Albayrak
authors.affiliation: Karadeniz Technical University, Faculty of Arts and Sciences, Department of Physics, 61080 Trabzon, Turkey.
authors.forename: Gökhan
authors.initials: G
authors.lastname: Apaydın
authors.affiliation: Aksaray University, Faculty of Arts and Sciences Department of Physics, 68100 Aksaray, Turkey.
authors.forename: Nefise
authors.initials: N
authors.lastname: Dilek
mesh_terms: D052160:Benzothiazoles / Q000737:chemistry; D001713:Biphenyl Compounds / Q000737:chemistry; D018360:Crystallography, X-Ray; D016166:Free Radical Scavengers / Q000737:chemistry*; D006860:Hydrogen Bonding; D007097:Imines / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D010636:Phenols / Q000737:chemistry*; D010851:Picrates / Q000737:chemistry; D010881:Piperidones / Q000737:chemistry; D011789:Quantum Theory; D017550:Spectroscopy, Fourier Transform Infrared; D055672:Static Electricity; D013451:Sulfonic Acids / Q000737:chemistry; D013816:Thermodynamics; D014732:Vibration
chemical_list: C000593265:(E)-4,6-dibromo-3-methoxy-2-((3-methoxyphenylimino)methyl)phenol; D052160:Benzothiazoles; D001713:Biphenyl Compounds; D016166:Free Radical Scavengers; D007097:Imines; D010636:Phenols; D010851:Picrates; D010881:Piperidones; D013451:Sulfonic Acids; C491664:dimethylpiperidone; C002502:2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid; C004931:1,1-diphenyl-2-picrylhydrazyl
keywords: Crystal structure; DFT and HF methods; Optimized geometry; Radical scavenging activities; Schiff base