title: 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.
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 μg/mL), DMPD+ (SC50 1.22±0.21 μg/mL), and ABTS+ (SC50 3.32±0.17 μg/mL) scavenging activities compared with standards (BHA, rutin, and trolox).
authors.affiliation: Giresun University, Technical Science Vocational High School, Department of Electric and Energy, 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: D000814:Aniline Compounds / Q000737:chemistry*; D000975:Antioxidants / Q000737:chemistry*; D002083:Butylated Hydroxyanisole / Q000737:chemistry; D002626:Chemistry, Pharmaceutical; D002839:Chromans / Q000737:chemistry; D018360:Crystallography, X-Ray; D016166:Free Radical Scavengers / Q000737:chemistry*; D006860:Hydrogen Bonding; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D019800:Phenol / Q000737:chemistry*; D012431:Rutin / Q000737:chemistry; D012545:Schiff Bases / Q000737:chemistry*; D012984:Software; D017550:Spectroscopy, Fourier Transform Infrared; D055672:Static Electricity
chemical_list: C000594891:4,6-dibromo-2-((2,6-dimethylphenylimino)methyl)-3-methoxyphenol; C000594890:4,6-dibromo-2-((3,5-dimethylphenylimino)methyl)-3-methoxyphenol; D000814:Aniline Compounds; D000975:Antioxidants; D002839:Chromans; D016166:Free Radical Scavengers; D012545:Schiff Bases; D002083:Butylated Hydroxyanisole; D019800:Phenol; D012431:Rutin; C010643:6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid
keywords: Crystal structure; DFT method; Radical scavenging activities; Schiff base