Green synthesis, X-ray crystallography, DFT and Hirshfeld analysis of C-2 symmetric 1,3-bis(4-ethylphenyl)triaz-1-ene

Saeed A., Tariq H. Z., Shabir G., Hökelek T., Bolte M., Ejaz S. A., ...More

Journal of Molecular Structure, vol.1274, 2023 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 1274
  • Publication Date: 2023
  • Doi Number: 10.1016/j.molstruc.2022.134523
  • Journal Name: Journal of Molecular Structure
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, INSPEC
  • Keywords: Crystal structure, Hirshfeld surface analysis, Thiourea, Natural Bond Analysis, Hydrogen bond
  • Hacettepe University Affiliated: Yes


© 2022 Elsevier B.V.A green synthesis of the novel symmetrical title molecule 1,3-bis(4-ethylphenyl)triazene (3) was achieved by self-coupling of 4-ethylaniline at room temperature via diazotization under 4.5–5.0 pH in water in excellent yield and purity. The structure of 3 was inferred by spectroscopic data, elemental analysis and corroborated by single crystal X-ray crystallography. It crystallizes in monoclinic I 2/a space group. In crystal structure, the intermolecular N–H···N hydrogen bonds link the molecules into infinite chains along the b-axis direction in which they are highly effective in the stabilization of the structure. The Hirshfeld surface analysis confirms the importance of H-atom contacts in establishing the packing. The large number of H···H and H···C/C···H interactions suggest that van der Waals interactions and hydrogen bonding play the major roles in the crystal packing. The evaluation of the electrostatic, dispersion and total energy frameworks indicates that the stabilization is dominated via the dispersion energy contribution. The HOMO and LUMO energies are −0.19401 and −0.5546 respectively.