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Journal of Innovation in Science, Engineering and Technology

Document Type

Original Study

Abstract

Schiff bases are an important class of imine compounds known for their structural versatility and biological activities, particularly as potential antimicrobial agents characterized by the azomethine (–C=N–) functional group, are widely recognized for its diverse biological activities. This study focuses on the synthesis and characterization of (E)-N-(3-phenylprop-2-en-1-ylidene)aniline to evaluate its potential as an antibacterial agent. The compound was synthesized via acid-catalyzed condensation of aniline and cinnamaldehyde under reflux for 2 hours in absolute ethanol. After purification through recrystallisation, the structure was confirmed using UV–Visible, FT-IR, 1H-NMR, and 13C-NMR spectroscopy. Thermal stability was assessed with thermogravimetric analysis (TGA), while electronic properties were calculated using the Hartree–Fock method. Antibacterial activity against E. coli and S. aureus was measured using the disk diffusion method. The UV–Vis spectrum exhibited a strong absorption band at 290nm corresponding to π → π * and n→ π * transitions, while FT-IR confirmed the formation of the azomethine (C=N) group. The 1H-NMR and 13C-NMR spectra validated the expected chemical environment of protons and carbons in the imine structure. Thermogravimetric analysis (TGA) revealed that the compound was thermally stable up to approximately 100–120°C before undergoing multi-step decomposition at higher temperatures. Computational studies performed using the Hartree–Fock (HF) method with a 3-21G basis set supported the experimental findings, confirming structural stability (no imaginary frequencies) and revealing an electron-rich nitrogen center (Mulliken charge -0.7017e), moderate dipole moment (2.13–2.53D), and significant polarizability, all indicative of potential biological activity. The Schiff base exhibited concentration-dependent antibacterial activity, with inhibition zones of 1.1 ± 0.58 cm for E. coli and 1.0 cm ± 0.58 for S. aureus at 2000 ppm, whereas lower concentrations (500 &1000 ppm) showed no activity. The research successfully demonstrated the synthesis of a stable, thermally stable Schiff base with antibacterial potential and these results suggest the compound is a promising candidate for pharmaceutical and material science development.

First Pages

1

Last Page

12

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