European Journal of Chemistry 2021, 12(2), 204-215 | doi: https://doi.org/10.5155/eurjchem.12.2.204-215.2088 | Get rights and content

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


Segun Daniel Oladipo (1) orcid , Tunde Lewis Yusuf (2,*) orcid , Sizwe Joshua Zamisa (3) orcid , Gideon Femi Tolufashe (4) orcid , Kolawole Ayodapo Olofinsan (5) orcid , Zikhona Tywabi-Ngeva (6) orcid , Nonhlangabezo Mabuba (7) orcid

(1) School of Chemistry and Physics, University of KwaZulu-Natal, Westville campus, Private Bag X54001, Durban, 4000, South Africa
(2) Department of Chemical Sciences, University of Johannesburg, Doornfontein, P.O. BOX 17011, 2028 Johannesburg, South Africa
(3) School of Chemistry and Physics, University of KwaZulu-Natal, Westville campus, Private Bag X54001, Durban, 4000, South Africa
(4) Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, 4169-007 Porto, Portugal
(5) Department of Biochemistry, Faculty of Natural and Applied Sciences, Nile University of Nigeria, Abuja, Nigeria
(6) Department of Chemistry, Faculty of Sciences, Nelson Mandela University, Port Elizabeth, 6000, South Africa
(7) Department of Chemical Sciences, University of Johannesburg, Doornfontein, P.O. BOX 17011, 2028 Johannesburg, South Africa
(*) Corresponding Author

Received: 27 Jan 2021 | Revised: 19 Mar 2021 | Accepted: 28 Mar 2021 | Published: 30 Jun 2021 | Issue Date: June 2021

Abstract


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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Keywords


Synthesis; Schiff bases; Drug-likeness; Crystal structure; Antioxidant properties; Density functional theory

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DOI: 10.5155/eurjchem.12.2.204-215.2088

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The College of Agriculture, Science, and Engineering, the University of Kwazulu-Natal and the Center for High-Performance Computing (CHPC), South Africa.

Citations

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Oladipo, S.; Yusuf, T.; Zamisa, S.; Tolufashe, G.; Olofinsan, K.; Tywabi-Ngeva, Z.; Mabuba, N. Eur. J. Chem. 2021, 12(2), 204-215. doi:10.5155/eurjchem.12.2.204-215.2088
Oladipo, S.; Yusuf, T.; Zamisa, S.; Tolufashe, G.; Olofinsan, K.; Tywabi-Ngeva, Z.; Mabuba, N. Synthesis, crystal structure with free radical scavenging activity and theoretical studies of Schiff bases derived from 1-naphthylamine, 2,6-diisopropylaniline, and substituted benzaldehyde. Eur. J. Chem. 2021, 12(2), 204-215. doi:10.5155/eurjchem.12.2.204-215.2088
Oladipo, S., Yusuf, T., Zamisa, S., Tolufashe, G., Olofinsan, K., Tywabi-Ngeva, Z., & Mabuba, N. (2021). Synthesis, crystal structure with free radical scavenging activity and theoretical studies of Schiff bases derived from 1-naphthylamine, 2,6-diisopropylaniline, and substituted benzaldehyde. European Journal of Chemistry, 12(2), 204-215. doi:10.5155/eurjchem.12.2.204-215.2088
Oladipo, Segun, Tunde Lewis Yusuf, Sizwe Joshua Zamisa, Gideon Femi Tolufashe, Kolawole Ayodapo Olofinsan, Zikhona Tywabi-Ngeva, & Nonhlangabezo Mabuba. "Synthesis, crystal structure with free radical scavenging activity and theoretical studies of Schiff bases derived from 1-naphthylamine, 2,6-diisopropylaniline, and substituted benzaldehyde." European Journal of Chemistry [Online], 12.2 (2021): 204-215. Web. 11 Dec. 2023
Oladipo, Segun, Yusuf, Tunde, Zamisa, Sizwe, Tolufashe, Gideon, Olofinsan, Kolawole, Tywabi-Ngeva, Zikhona, AND Mabuba, Nonhlangabezo. "Synthesis, crystal structure with free radical scavenging activity and theoretical studies of Schiff bases derived from 1-naphthylamine, 2,6-diisopropylaniline, and substituted benzaldehyde" European Journal of Chemistry [Online], Volume 12 Number 2 (30 June 2021)

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