Akademik Veri Yönetim Sistemi
ChemistrySelect, cilt.10, sa.35, 2025 (SCI-Expanded)
The present study investigates the synthesis, characterization, x-ray structure, DFT, and antimicrobial properties of two bromo-based ortho-vanillin compounds (1 and 2). 1 and 2 crystallized in the space group P21/c and P21/n and have unique supramolecular architectures, including O····Br and CHO(π)····CHO(π). Comprehensive DFT calculations revealed that both compounds have electronic properties. Hirshfeld surface (HS) revealed major H…O (26.8% in 1 and 27.8% in 2) and minor H…Br contacts in the crystal structure. MEP and AIM provide information about the electronic charge distribution and the hydrogen bond interactions. TD-DFT calculations confirm the origin of the absorption spectroscopic transitions. FMO confirms that 2 has higher reactivity than 1. Nonlinear optical properties show that 1 has a higher response than 2, based on dipole moment (µ), polarizability (α), and hyperpolarizability (β) values. The ADME/T parameters explore the compound's pharmacological properties. The agar well diffusion method was employed to evaluate the antimicrobial efficacy against both Gram-positive (B. subtilis and S. aureus) and Gram-negative (E. coli, P. aeruginosa, K. pneumoniae, and C. albicans) microbial strains. The compounds were found to be potent against Gram-positive bacterial strains. Molecular docking simulation confirms that 1 and 2 exhibit bactericidal affinity due to strong binding interactions between bioproteins and receptors (1 and 2), which is further rationalized by a structure–activity relationship (SAR).