Synthesis, crystal structure, DFT calculation and Hirshfeld surface analysis of N-(4-methyl phenyl)-2-(3-nitro-benzamido) benzamide

Abstract

A new bis amide N-(4-methylphenyl)-2-(3-nitrobenzamide) benzamide was synthesized from a ring-opening reaction of 2-(3-nitrophenyl)-4H-benzoxazin-4-one, with 4-methyl aniline in a shorten reaction time (1.0 min) and characterized using different spectroscopic techniques (FT-IR, ¹H-NMR, ¹³C-NMR) and single-crystal X-ray diffraction (XRD). In the crystal lattice, the molecules are linked by N–H···O and C–H···O hydrogen bonds. The Hirshfeld surface analysis mapped over shape index, curvedness indices, d_norm revealed strong H...H and H...O/O...H and intermolecular connections a key contributors to crystal packing structure. Density functional theory (DFT) calculations were applied with B3LYP/6-311G(d) level to provide theoretical data along with HOMO-LUMO electronic energy with the MEP map.

KEY WORDS: Benzamide, Crystal structure, DFT calculation, Hirshfeld surface

Bull. Chem. Soc. Ethiop. 2024, 38(1), 229-239. 
DOI: https://dx.doi.org/10.4314/bcse.v38i1.17