Some Nitrogen Rich Energetic Material Synthesis by Nucleophilic Substitution Reaction from Polynitro Aromatic Compounds

Gürpınar K., Gürsoy Tuncer Y., Sopacı Ş. B., Akay M. A., Nazır H., Svoboda I., ...More

Acta Chimica Slovenica, vol.68, no.4, pp.930-944, 2021 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 68 Issue: 4
  • Publication Date: 2021
  • Doi Number: 10.17344/acsi.2021.6904
  • Journal Name: Acta Chimica Slovenica
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Central & Eastern European Academic Source (CEEAS), Chemical Abstracts Core, EMBASE, MEDLINE, Directory of Open Access Journals, DIALNET
  • Page Numbers: pp.930-944
  • Keywords: Energetic material, nitrogen-rich material, formation enthalpy, thermokinetic analysis, Kamlet-Jacobs equation, antimicrobial activity, THERMAL-DECOMPOSITION, HYDROGEN-BOND, KINETICS, PYROLYSIS, BIOMASS, DEGRADATION
  • Ankara University Affiliated: Yes


Three new nitrogen-rich energetic compounds, N-(5-chloro-2,4-dinitrophenyl)hydrazine (1), N-(5-chloro-2,4-dinitrophenyl)guanidine (2) and N-(5-chloro-2,4-dinitrophenyl)-4-aminopyrazole (3) prepared by the nucleophilic substitution reaction of 1,3-dichloro-4,6-dinitrobenzene with hydrazine, guanidinium carbonate and 4-aminopyrazole. The compounds were characterized by 1H NMR, 13C NMR, IR and mass spectroscopy. Only compound 2 could be prepared in a suitable crystal and molecular model was determined by X-ray analysis. Compounds were investigated by TG and DSC. Thermal degradation and thermokinetic behavior were investigated by Ozawa–Flynn–Wall and Kissinger–Akahira–Sunose techniques. Compounds were observed to be prone to exothermical thermal decomposition. HOMO and LUMO levels, theoretical formation enthalpy and electrostatic maps were calculated by Gaussian09. The detonation velocity and pressure were calculated by Kamlet–Jacobs equation. The compounds were assayed for antimicrobial properties.