Influence of mono- and di-bromo substitution on the structure conformation and supramolecular assembly of schiff base derivatives

Udaya Kumar, A. H. and Dibdalli, Yuvaraja and Morales-Verdejo, Cesar and Khadri M․ J․, Nagesh and Mahesha and Lokanath, N. K. (2026) Influence of mono- and di-bromo substitution on the structure conformation and supramolecular assembly of schiff base derivatives. Journal of Molecular Structure, 1353. p. 144582. ISSN 1872-8014

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Abstract

The positioning of substituents plays a critical role in dictating molecular conformation and supramolecular assembly, essential for the rational design of functional crystalline materials. In this work, two Schiff base compounds were synthesized via the condensation of ethyl 2-aminoisonicotinate with 3‑bromo-5-hydroxybenzaldehyde and 3,5-dibromo-5-hydroxybenzaldehyde. Single crystals suitable for X-ray diffraction were obtained by slow evaporation, and both compounds crystallized in the triclinic space group P̅1. Structural analysis revealed nearly planar geometries with dihedral angles between the hydroxyphenyl and ethoxypyridyl moieties, connected through an azomethine bridge. The planarity facilitated robust π–π stacking interactions and hydrogen bonding, both contributing to crystal packing stabilization. Comparative assessment showed that the second bromine atom significantly modifies intermolecular interactions and supramolecular organization. Hirshfeld surface, fingerprint plots, enrichment ratios, and QTAIM analyses quantitatively characterized these contacts, while DFT calculations indicated enhanced π-electron delocalization and reduced HOMO–LUMO gaps. Molecular docking against Staphylococcus aureus TyrRS revealed π-stacking-mediated ligand–receptor interactions with good binding energies, highlighting biological relevance. This study provides quantitative insight into how positional substitution governs molecular packing, noncovalent interactions, and protein-ligand interaction leading to the potential functional applications.

Item Type:	Article
Uncontrolled Keywords:	Schiff base, π‧‧‧π stacking interactions, QTAIM, Antibacterial studies, Molecular docking
Subjects:	D Physical Science > Physics
Divisions:	Department of > Physics
Depositing User:	C Swapna Library Assistant
Date Deposited:	17 Dec 2025 05:23
Last Modified:	17 Dec 2025 05:23
URI:	http://eprints.uni-mysore.ac.in/id/eprint/18215

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