Synthesis, structural, spectroscopic investigation, Hirshfeld surface analysis and DFT calculation of a new spiro compound including 4-nitroaniline moiety

A new spiro compound, C 14 H 13 N 3 O 6 (NHD) was prepared through the reaction of 6,10-dioxaspiro[4.5]decane-7,9‑dione with diazotized solution of 4-nitroaniline in ethanol. The structural characteristics of NHD were investigated using spectroscopy (FT-IR, UV-is and 1 H and 13 C NMR) and computational analysis utilizing B3LYP/6–311G(d,p) level. Theoretical and experimental results for optimizing molecular geometry, infrared vibrational frequencies, and UV–Vis spectra were found to be consistent. Hirshfeld surface analysis had been used to explain intermolecular interaction and π···π stacking interactions. 2D fingerprint studies confirmed that O···H/H···O contributions make up the greatest contributors (43.6 %) in NHD. Additionally, (HOMO-LUMO) energies, global reactivity properties, MEP and NBO were investigated at the same level. Finally, NHD is thermally stable up to 195 ℃ according to TG/DTA analysis.