Synthesis, crystal structure with free radical scavenging activity and theoretical studies of Schiff bases derived from 1-naphthylamine, 2,6-diisopropylaniline, and substituted benzaldehyde

化学 DPPH 单斜晶系 特罗洛克 晶体结构 氢键 密度泛函理论 席夫碱 亚胺 分子间力 结晶学 单晶 药物化学 有机化学 抗氧化剂 分子 计算化学 催化作用
作者
Segun D. Oladipo,Tunde L. Yusuf,Sizwe J. Zamisa,Gideon F. Tolufashe,Kolawole Olofinsan,Zikhona Tywabi-Ngeva,Nonhlangabezo Mabuba
出处
期刊:European Journal of Chemistry [European Journal of Chemistry]
卷期号:12 (2): 204-215 被引量:12
标识
DOI:10.5155/eurjchem.12.2.204-215.2088
摘要

Three Schiff bases 1-(4-chlorophenyl)-N-(naphthalen-1-yl)methanimine (1), 1-(4-methoxy phenyl)-N-(naphthalen-1-yl)methanimine (2), and 1-(4-chlorophenyl)-N-(2,6-diisopropyl phenyl)methanimine (3) were synthesized and characterized by elemental analysis, 1H and 13C NMR, FT-IR and UV-Visible spectroscopic techniques. The crystal structure of compound 3 was obtained and it revealed that the compound crystallized in a monoclinic space group P21/n and there exists an intermolecular hydrogen bond in a phenyl-imine form with C-H⋯N. Crystal data for C19H22ClN: a = 7.28280(10) Å, b = 9.94270(10) Å, c = 24.0413(2) Å, β = 97.0120(10)°, V = 1727.83(3) Å3, Z = 4, μ(Mo Kα) = 0.215 mm-1, Dcalc = 1.1526 g/cm3, 14038 reflections measured (12.42° ≤ 2Θ ≤ 52.74°), 3448 unique (Rint = 0.0223, Rsigma = 0.0182) which were used in all calculations. The final R1 was 0.0337 (I≥2u(I)) and wR2 was 0.0927 (all data). The free radical scavenging activities of all three compounds were assayed using DPPH, FRAP, and OH assays. According to results obtained, compound 2 shows effective DPPH- (IC50 = 22.69±0.14 μg/mL), FRAP+ (IC50 = 28.44±0.12 μg/mL), and OH- (IC50 = 27.97±0.16 μg/mL) scavenging activities compared with compounds 1 and 3 but less than standard antioxidant compound Trolox (TRO). Additionally, theoretical calculations for the three complexes were performed by using density functional theory (DFT) calculations at the B3LYP/6-31++G(2d,2p) level in the ground state to obtain an optimized geometrical structure and to perform an electronic, molecular electronic potential surface and natural bond orbital (NBO) analysis. The geometrical calculation obtained was found to be consistent with the experimental geometry. Further analysis was conducted using the in silico technique to predict the drug likeness, molecular and ADME properties of these molecules.
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