Investigation of energetic materials prepared by reactions of diamines with picryl chloride

Atakol, Melike; Atakol, Arda; Yigiter, Aynur Ozler; Svoboda, Ingrid; Atakol, Orhan

doi:10.1007/s10973-016-5800-4

Cited by 9 publications

(7 citation statements)

References 25 publications

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“…This in observed with numerous studies in the literature [13 -17]. Furthermore, it is reported that, if a substituent is attached, via amino bridge, to the aromatic rings involving nitro group at ortho position, decomposition reaction again resembles the furoxane mechanism [4,43,44]. In the same studies, N (2,4,6trinitrophenyl) hydrazine is reported to be similarly decomposed at around 190°C.…”

Section: Resultssupporting

confidence: 67%

The Thermal Investigation, Thermokinetic Analysis and Antimicrobial Activity of Two New Energetic Materials Obtained from Nucleophilic Substitution of Nitro Pyridine Ring

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et al. 2018

Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi

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2-Chloro-3 and 5-dinitropyridine were put into reaction with hydrazine and 3-aminopyrazole to obtain two new highly nitrogenous energetic substances. These energetic substances are; N(3,5-dinitropyridyn-2-yl) hydrazine (I), and N(3,5dinitropyridyn-2-yl)3-aminopyrazole (II). These substances were characterized with element analysis, mass spectroscopy, IR spectroscopy, 1 HNMR and 13 CNMR methods. Besides, the substances were analyzed with TG and thermal decomposition mechanisms were interpreted. Apart from these, isothermal and thermal kinetic analysis methods were used to reveal out the activation energies and Arrhenius pre-exponential factors. Thermodynamic parameters of decomposition reactions were measured by using these values. Nitrofuroxane ring was concluded to be the sub-product in thermal decomposition reactions. Gaussian 09 software algorithms were used to measure the standard formation enthalpy values of the two energetic substances. Using these values, the reaction enthalpy value of the thermal decomposition reaction according to Hess's law and the result obtained was compared with the value obtained from the differential scanning calorimetry method. Experimental and theoretical results were observed to be similar. In addition to these, antimicrobial effects of the highly nitrogenous energetic substances were measured for 5 different bacteria and their antifungal effects were measured for one type of fungus. As they were highly nitrogenous, the bacteria were found to be using the nitrogen in these substances for nutritional purpose.

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Section: Resultssupporting

confidence: 67%

The Thermal Investigation, Thermokinetic Analysis and Antimicrobial Activity of Two New Energetic Materials Obtained from Nucleophilic Substitution of Nitro Pyridine Ring

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Acar

Sopacı

et al. 2018

Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi

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“…While prodrugs TNA7-8 are new compounds, prodrugs TNA1-6 are known in the literature. [14][15][16][17][18][19] The characterization data of known compounds, which were synthesized according to the known methods with some experimental modifications such as different base, solvent, temperature, and reaction time, were compared with reported values.…”

Section: Resultsmentioning

confidence: 99%

Prodrugs for Nitroreductase Based Cancer Therapy‐5: Development of Trinitroaniline Prodrugs/Ssap‐NtrB Combinations for Liver Cancer Using Intracellular and Extracellular Conditions

et al. 2021

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In this study, a series of trinitroaniline derivatives (TNA1‐8) were synthesized and investigated as potential antitumor agents for enzyme‐prodrug therapy. Enzymatic efficiency of Ssap‐NtrB on prodrug candidates was determined with HPLC analysis and kinetic studies. The anti‐proliferative properties of compounds were determined against four cancer cell lines (Hep3B, PC3, HT‐29, and Saos‐2) and a healthy cell line (HUVEC) via MTT assay. Intracellular and extracellular prodrug‐enzyme treatments were carried out on Hep3B cells. Herewith, the expression of the Ssap‐NtrB gene was confirmed with this study. IC50 values of piperidine and 1,3‐cyclohexyl derivatives (TNA4 and TNA7) were identified as 1.724 nM and 1.640 nM at extracellular conditions. In intracellular conditions, it was determined as 0.293 μM and 0.393 μM, respectively. In summary, 2,4,6‐trinitroaniline derivatives, especially compounds TNA4 and TNA7 might be used as prodrug candidates along with Ssap‐NtrB for hepatocellular carcinoma therapy and the development of new prodrugs at cancer treatments.

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“…[7][8][9] A large number of energetic substances prepared by this method were reported in the literature. [10][11][12][13][14] Our choice of hydrazine and guanidine is since they are rich in nitrogen and the choice of 4-aminopyrazole is because of its heterocyclic structure. If hydrazine and guanidine are employed in nucleophilic substitution reactions, it is highly probable that two amino groups may be substituted which may result in symmetric molecules and the final product is a mixture.…”

Section: Introductionmentioning

confidence: 99%

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

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et al. 2021

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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.

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Investigation of energetic materials prepared by reactions of diamines with picryl chloride

Cited by 9 publications

References 25 publications

The Thermal Investigation, Thermokinetic Analysis and Antimicrobial Activity of Two New Energetic Materials Obtained from Nucleophilic Substitution of Nitro Pyridine Ring

The Thermal Investigation, Thermokinetic Analysis and Antimicrobial Activity of Two New Energetic Materials Obtained from Nucleophilic Substitution of Nitro Pyridine Ring

Prodrugs for Nitroreductase Based Cancer Therapy‐5: Development of Trinitroaniline Prodrugs/Ssap‐NtrB Combinations for Liver Cancer Using Intracellular and Extracellular Conditions

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

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