Details

Autor(en) / Beteiligte

• Abu-Yamin, Abdel Aziz
• Jbarah, Abdel Aziz Qasem Mohammad
• Khalyfeh, Khaled Al
• Matar, Suzan
• Alqasaimeh, Muawia
• Rüffer, Tobias
• Lang, Heinrich

Titel

Crystal structure, spectroscopic studies, DFT calculations, and biological activity of 5-bromosalicylaldehyde–based Schiff bases

Ist Teil von

• Journal of molecular structure, 2022-08, Vol.1262, p.132976, Article 132976

Ort / Verlag

Elsevier B.V

Erscheinungsjahr

2022

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• •Crystal structure of 5-Bromosalicylaldehydes based Schiff base.•Comparative study between theoretical and experimental spectroscopic data of 5-Bromosalicylaldehydes based Schiff base.•Biological activity of 5-Bromosalicylaldehydes based Schiff base. A single-crystal X-ray diffraction investigation verified the chemical structure of (E)-ethyl-4-(5‑bromo-2-hydroxybenzylidene amino)benzoate (1). Schiff base 1 crystallizes in the triclinic space group P1¯ with unit cell dimensions of a = 5.961(2), b = 7.499(3), c = 17.112(6) Å and unit cell angles of α = 95.565(12), β = 94.192 (13), γ = 104.689(13)°. Density functional theory (DFT) calculations utilizing the B3LYP level of theory and the 6–31+G(d,p) basis set have validated the reported experimental geometries and spectroscopic data (UV–vis, FT-IR, 1H NMR) for 1 and 2-((E)-(4H-1,2,4-triazole-4-ylimino)methyl)-4-bromophenol (2), whereby Schiff base 2 corresponds to a literature known compound. The optimized geometry generated from DFT simulations was used to compute the molecules' vibrational frequencies. The experimentally observed frequencies are compared to the DFT calculated ones. TD-DFT simulations were also used to study the compounds' molecular electronic structures. The results of UV–vis spectroscopy, both experimental and computed, support the synthesis of the target compounds. The calculations of the molecular electrostatic potential surfaces of compounds 1 and 2 were performed. According to the calculated molecular electrostatic potential results, the reactive sites of 1 and 2 were determined. The compounds showed bactericidal activity against selective Gram-positive and Gram-negative bacteria except for 2 with no candidacidal activity compared to 1. In vitro cytotoxicity of 1 and 2 was screened for MCF-7 and fibroblasts cell lines by MTT assay. Results showed that 1 is more cytotoxic than 2 on MCF-7 but nontoxic on fibroblasts indicating that 1 has potential for further development in the search of safe and potent anticancer agent.