Synthesis, crystallographic structure, Hirshfeld surface analysis and DFT calculations of Schiff base (Z)-4-methyl-2-(((3-nitrophenyl)imino)methyl) phenol

Hamidov E., Agar A., El-Kelany K. E., Dege N., Yousef T. A., Ferjani H., ...More

JOURNAL OF MOLECULAR STRUCTURE, vol.1310, 2024 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 1310
  • Publication Date: 2024
  • Doi Number: 10.1016/j.molstruc.2024.138319
  • Journal Name: JOURNAL OF MOLECULAR STRUCTURE
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, Chimica, Compendex, INSPEC
  • Ondokuz Mayıs University Affiliated: Yes

Abstract

The (Z)-4-methyl-2-(((3-nitrophenyl)imino)methyl)phenol (C15H14N2O3) (MNIMP) was prepared by condensation of 2-hydroxy-5-methyl-benzaldehyde and 2-methyl-4-nitro-phenylamine in ethanol and characterized by NMR (1H and 13C), IR and UV-Visible spectroscopy. The molecular crystal packing has been quantitatively explored via Hirshfeld surface analysis, where the intramolecular C - H & ctdot;O bonding represents the principle contribution that stabilizes the crystal packing, with an overall 27.5 % for O & ctdot;H interactions. The outcomes of a theoretical investigation conducted at the B3LYP/6-311++G(d,p) level using the DFT approach are in strong agreement with the results of the experiment. The experimental outcome is compatible with the optimized structure. Z)-4-methyl-2-(((3-nitrophenyl)imino)methyl)phenol vibrational spectrum is calculated at the same theoretical level (DFT/ B3LYP/6-311++G(d,p)), and it is discovered that the theoretically estimated vibrational frequencies and assignments accord well with experimental FT-IR values.