Synthesis, structural elucidation, Hirshfeld surface, DFT, pharmacophore, and in silico studies of a piperonal derivative: A study based on experimental and theoretical methods

Darshan, D. and Santhosh, C. and Singh, Ravi K. and Chethan, B. S. and Lohith, T. N. and Sadashiva, M. P. and Sunil, K. and Hemalatha, P. (2026) Synthesis, structural elucidation, Hirshfeld surface, DFT, pharmacophore, and in silico studies of a piperonal derivative: A study based on experimental and theoretical methods. Journal of Molecular Structure, 1352. p. 144555. ISSN 1872-8014

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Abstract

A novel piperonal derivative, 2-((benzod1,3dioxol-5-ylmethyl)amino)-2-thioxo-N-(p-tolyl)acetamide (3a) was synthesized and extensively characterized using advanced spectroscopic techniques (FT-IR, NMR), single-crystal X-ray diffraction, Hirshfeld surface analysis, Density Functional Theory (DFT) calculations, and molecular docking studies. Structural analyses confirmed the presence of the characteristic amide linkage and elucidated distinct supramolecular architectures stabilized predominantly by hydrogen bond (NH…O) and CH…π stacking interactions. Hirshfeld surface mappings quantified intermolecular interactions, revealing significant contributions from aromatic stacking contacts. The DFT calculations were performed using B3LYP functional and 6–311++G (d,p) basis set. Quantum chemical analyses highlighted extensive electron de-localization across the molecule, with subtle differences in electronic descriptors suggesting slightly higher reactivity. The energy gap of the compound is found to be 4.000 eV. The docking analysis of 3a with the protein 5F19, which is implicated in dual-action therapeutic targeting inflammation and tumorigenesis through soluble epoxide hydrolase inhibition.

Item Type:	Article
Uncontrolled Keywords:	Piperonal derivative, X-ray crystallography, Hirshfeld surface, Density functional theory, Molecular docking, Non-covalent interactions
Subjects:	C Chemical Science > Chemistry
Divisions:	Department of > Chemistry
Depositing User:	C Swapna Library Assistant
Date Deposited:	17 Dec 2025 05:30
Last Modified:	17 Dec 2025 05:30
URI:	http://eprints.uni-mysore.ac.in/id/eprint/18216

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