Open AccessSome Nitrogen Rich Energetic Material Synthesis by Nucleophilic Substitution Reaction from Polynitro Aromatic Compounds
Author(s) -
Kübra Gürpınar,
Y. Tuncer,
Şaziye Betül Sopacı,
M. Abdülkadir Akay,
Hasan Nazır,
Ingrid Svoboda,
Orhan Atakol,
Emine Kübra İnal
Publication year - 2021
Publication title -
acta chimica slovenica
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.289
H-Index - 46
eISSN - 1580-3155
pISSN - 1318-0207
DOI - 10.17344/acsi.2021.6904
Subject(s) - chemistry , nucleophilic substitution , hydrazine (antidepressant) , thermal decomposition , nucleophile , standard enthalpy of formation , nucleophilic aromatic substitution , nitrogen , substitution reaction , homo/lumo , carbon 13 nmr , hydrate , enthalpy , medicinal chemistry , organic chemistry , molecule , catalysis , physics , chromatography , quantum mechanics
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.