2024-03-28T19:52:51Z
https://www.eurjchem.com/index.php/eurjchem/oai
oai:ojs.www.eurjchem.com:article/2088
2021-09-30T06:33:34Z
eurjchem:ART
driver
Synthesis, crystal structure with free radical scavenging activity and theoretical studies of Schiff bases derived from 1-naphthylamine, 2,6-diisopropylaniline, and substituted benzaldehyde
Oladipo, Segun Daniel
Yusuf, Tunde Lewis
Zamisa, Sizwe Joshua
Tolufashe, Gideon Femi
Olofinsan, Kolawole Ayodapo
Tywabi-Ngeva, Zikhona
Mabuba, Nonhlangabezo
Synthesis
Schiff bases
Drug-likeness
Crystal structure
Antioxidant properties
Density functional theory
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.
Atlanta Publishing House LLC
2021-06-30
info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
application/pdf
text/plain
https://www.eurjchem.com/index.php/eurjchem/article/view/2088
10.5155/eurjchem.12.2.204-215.2088
European Journal of Chemistry; Vol. 12 No. 2 (2021): June 2021; 204-215
2153-2257
2153-2249
eng
https://www.eurjchem.com/index.php/eurjchem/article/view/2088/pdf_2088
https://www.eurjchem.com/index.php/eurjchem/article/view/2088/2658
Copyright (c) 2021 Authors