Gem-dinitro compounds in organic synthesis. 3. Syntheses of 4-nitro-1,2,3-triazoles from gem-dinitro compounds

Baryshnikov, A. T.; Erashko, V. I.; Zubanova, N. I.; Уграк, Б. И.; Shevelev, S. A.; Fainzil'berg, A. A.; Laikhter, A. L.; Mel'nikova, L. G.; Семенов, В. В.

doi:10.1007/bf01150904

Cited by 27 publications

(20 citation statements)

References 14 publications

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“…It is noted that the C 1 -N 1 BDE is the biggest for compound (5) and equal to 68.2 kcal/mol, which is much bigger than those of the C 3 -N 3 and C 4 -N 4 bonds, the C 4 -N 4 BDE is the smallest. For compound (6), the BDEs of the C 3 -N 3 and Table 1 Bond dissociation energies (BDE, kcal/mol) for seven title compounds at B3LYP/6-31G* and B3P86/6-31G* levels Compound B3LYP/6-31G* B3P86/6-31G* H 50 Numbers in bold mean that the corresponding bond is most reactive in the studied compound C 5 -N 5 bonds are equivalent, and their BDEs are all equal to 63.9 kcal/mol. The C 1 -N 1 BDE is the biggest and equal to 68.1 kcal/mol, which means that the C 3 -N 3 bond should be initial scission step.…”

Section: Resultsmentioning

confidence: 99%

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Theoretical studies on a series of 1,2,3-triazoles derivatives as potential high energy density compounds

Zhang

2011

Struct Chem

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Based on the full-optimized molecular geometric structures at B3LYP/6-31G* and B3P86/6-31G* levels, the densities (q), detonation velocities (D), and pressures (P) for a series of 1,2,3-triazole derivatives, as well as their thermal stabilities, were investigated to look for high energy density compounds (HEDCs). The heats of formation (HOFs) are also calculated via designed isodesmic reactions. The calculations on the bond dissociation energies (BDEs) indicate that the BDEs of the initial scission step are between 53 and 70 kcal/mol, and 4-nitro-1,2,3-triazole is the most reactive compound, while 1-(2 0 ,4 0 -dinitrophenyl)-5-nitro-1,2,3-triazole is the least reactive compound for 1,2,3-triazole derivatives studied. The condensed phase heats of formation are also calculated for the title compounds. These results would provide basic information for the further studies of HEDCs. The detonation data of 1-(3 0 ,4 0 -dinitrophenyl)-4-nitro-1,2,3-triazole and 1-(2 0 ,4 0 -dinitrophenyl)-4-nitro-1,2,3-triazole show that they meet the requirement for HEDCs.

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Section: Resultsmentioning

confidence: 99%

“…For the isodesmic reaction (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13), heat of reaction DH 298 at 298 K can be calculated from the following equation:…”

Section: Theory and Computational Detailsmentioning

confidence: 99%

Theoretical studies on a series of 1,2,3-triazoles derivatives as potential high energy density compounds

Zhang

2011

Struct Chem

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“…Material 4-Amido-5-nitro-1,2,3-triazol (≥99.5%), guanylurea hydrochloride and picryl chloride were all prepared and purified according to a reported method 6 by Xi'an Modern Chemistry Research Institute, and other reagents were of A.R. grade.…”

Section: Methodsmentioning

confidence: 99%

“…According to the synthetic method in the reference, 6 4-amino-5-nitro-1,2,3-triazole was synthesized using 4-amido-5-nitro-1,2,3-triazole as the initiative material by the reaction of rearrangement (Scheme 1).…”

Section: Synthesis Of 4-amino-5-nitro-123-triazole (Antz)mentioning

confidence: 99%

“…4-Amino-5-nitro-1,2,3-triazole (ANTZ), recently being identified as a kind of potential high performance insensitive explosive, [1][2][3][4][5][6] has some desirable attributes, including a high nitrogen content of 54%, high density 1.837 g•cm -3 (at 25 ℃ with measuring method of 401.1, GJB772A-97), combustion heat of 1350.501 kJ•mol -1 and relatively low sensitivity to shock or impact-included ignition with H 50 of 154 cm [with drop-weight of 10 kg and measuring method of 601.2, GJB772A-97, while that of cyclotetramethylenetetranitroamine (HMX) is 32 cm under the same measuring condition], which can be used as a main insensitive energetic component of cast explosives and propellants [7][8][9] in order to substitute 1,3,5-triamino-2,4,6-trinitrobenzene (TATB), cyclotrimethylenetrinitramine (RDX) or HMX. There are several reports on the synthesis methods, characterization and the detonation properties of ANTZ, whose detonation velocity is 8909.403 m•s -1 and detonation pressure 35.657 GPa, 10,11 but there is no report about the derivatives of ATNZ.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Characterization and Thermal Behaviors of 4‐Amino‐5‐nitro‐1,2,3‐triazole (ANTZ) and Its Derivatives

Wang

Li²,

Huo

et al. 2010

Chin. J. Chem.

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4-Amino-5-nitro-1,2,3-triazole (ANTZ) and its derivatives, such as 2-(4-amino-5-nitro-1,2,3-trazole-1-yl)-1,3,5-trinitrobenzene (T-ANTZ) and 4-amino-5-nitro-1,2,3-triazole (M-ANTZ), were synthesized and characterized, whose structures were confirmed by IR, NMR and elemental analysis. The thermal behaviors of ANTZ, T-ANTZ and M-ANTZ were studied by the methods of DSC and TG-DTG, and the results showed that there is an obvious melting process of ANTZ with melting point of 278.38 ℃, while there is no melting process in the thermal behavior of T-ANTZ and M-ANTZ (the derivatives of ATNZ).

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Selective Preparation of 3,4,5‐Trinitro‐1H‐Pyrazole: A Stable All‐Carbon‐Nitrated Arene

Hervé¹,

Roussel²,

Graindorge³

2010

Angewandte Chemie

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Gem-dinitro compounds in organic synthesis. 3. Syntheses of 4-nitro-1,2,3-triazoles from gem-dinitro compounds

Cited by 27 publications

References 14 publications

Theoretical studies on a series of 1,2,3-triazoles derivatives as potential high energy density compounds

Theoretical studies on a series of 1,2,3-triazoles derivatives as potential high energy density compounds

Synthesis, Characterization and Thermal Behaviors of 4‐Amino‐5‐nitro‐1,2,3‐triazole (ANTZ) and Its Derivatives

Selective Preparation of 3,4,5‐Trinitro‐1H‐Pyrazole: A Stable All‐Carbon‐Nitrated Arene

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