- Some Nitrogen Rich Energetic Material Synthesis by Nucleophilic Substitution Reaction from Polynitro Aromatic Compounds
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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.
- ?nal, Emine Kübra,Akay, M. Abdulkadir,Atakol, Orhan,Gürp?nar, Kübra,Naz?r, Hasan,Sopac?, ?. Betül,Svoboda, Ingrid,Tuncer, Yaprak Gürsoy
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p. 930 - 944
(2021/12/31)
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- peri-Substituted Imidazopyridines. A New Reductive Elimination Reaction
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A new reductive elimination reaction of 3,5-disubstituted imidazopyridines (3) with hydrazine is reported.Thus on treatment of the 3,5-dibromo (7a), 5-bromo-3-nitro (7b), and 3,5-dinitro (4) derivatives with hydrazine hydrate in hot ethanol, the bromine and nitro groups are replaced by hydrogen.A mechanism based on the conjugated relationship of these peri-substituents is proposed and used to explain the reported conversion of 1,3,5-trichloro-2,4,6-trinitrobenzene (9) into 1,3-dichloro-4,6-dinitrobenzene (10).A variety of other 3-nitro-5-substituted imidazopyridines (15)-(18) is described, but these could not be cyclised to 1,2,4-triazacyclopentindenes.The 3-amino-5-methoxycarbonyl derivative (19a) cyclises to the triazacyclopentindenone (20) with sodium methoxide.
- Rees, Charles W.,Smith, David I.
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p. 1159 - 1164
(2007/10/02)
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- REGARDING THE REACTION OF S-TRICHLOROTRINITROBENZENE WITH HYDRAZINE
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The reaction of S-trichlorotrinitrobenzene with hydrazine is shown to give 1,3-dihydrazino-4,6-dinitrobenzene (4), not S-trihydrazinotrinitrobenzene as previously reported.
- Lawrence, G. William,Adolph, Horst G.
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p. 1615 - 1618
(2007/10/02)
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