Energetic Nitrogen‐Rich Derivatives of 1,5‐Diaminotetrazole

Joo, Young Hoon; Twamley, Brendan; Garg, Sonali; Shreeve, Jean’ne M.

doi:10.1002/anie.200801886

Cited by 152 publications

(86 citation statements)

References 26 publications

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“…[16] Nevertheless the low stability and short shelf life of 3a prompted us to examine cyanogen azide for achieving the synthesis of the desired 5-aminotetrazole. An additional advantage of using this reagent was that no anhydrous conditions were required to perform the reaction.…”

Section: Resultsmentioning

confidence: 99%

Application of Primary Allylamines from Morita–Baylis–Hillman Adducts: Cyanogen Azide Mediated Synthesis of Substituted 5‐Aminotetrazoles and Their Attempted Transformation into Tetrazolo[1,5‐a]pyrimidinones

et al. 2010

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A general protocol for the synthesis of substituted 5-aminotetrazoles by treating cyanogen azide with primary allylamines afforded either by S N 2 or S N 2Ј reactions of MoritaBaylis-Hillman acetates of acrylate has been developed. The base-promoted intramolecular cyclizations of these tetrazoles afford highly substituted 2-azidopyrimidin-4(3H)-ones instead of the expected tetrazolopyrimidinone due to azidetetrazole tautomerism. Nevertheless it has been discovered

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Section: Resultsmentioning

confidence: 99%

Application of Primary Allylamines from Morita–Baylis–Hillman Adducts: Cyanogen Azide Mediated Synthesis of Substituted 5‐Aminotetrazoles and Their Attempted Transformation into Tetrazolo[1,5‐a]pyrimidinones

et al. 2010

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“…The thermal decomposition products of these energetic ionic salts are mostly nitrogen, with low vapor pressure [5][6][7] and high density, so they are friendly to the environment.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Structure, and Energetic Properties of 1,5‐Diaminotetrazolium Sulfate Salts

Yao

Han

Zhang

et al. 2015

Journal of Heterocyclic Chem

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in Wiley Online Library (wileyonlinelibrary.com).1,5-diaminotetrazolium chloride (DATC) and 1,5-diaminotetrazolium sulfate (DATS) were synthesized in this work. The structures of DATS and DATC were characterized. The single crystal of DATS was first cultured, and its structure was analyzed. The thermal behavior of DATS was investigated. The activation energy and pro-exponential factor were calculated, E k = 120.86 KJ/mol, A k = 10 12.96 s À1. The density, heat of formation, detonation pressure, and detonation velocity of DATS were first calculated. The detonation pressure and detonation velocity of DATS are P = 11.877 GPa, D = 5.617 km s À1, which are smaller than those of 1,5-diaminotetrazolium nitrate (DATN) (P = 33.3GPa, D = 8.77 km s À1).

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“…Azoles and their derivatives are part of these high nitrogen-contented heterocyclic compounds. With fascinating structures and excellent properties, azole-based derivatives, polycyclic compounds, complexes and salts have been intensively studied in an effort to meet the increased demand for new energetic materials [5,[10][11][12][13][14][15][16][17][18]. Klapötke and his co-workers [19][20][21][22][23] and Shreeve's [17,24,25] group have performed lots of studies of nitrogen-rich energetic compounds on the basis of triazole, tetrazole and their derivatives.…”

Section: Introductionmentioning

confidence: 99%

Theoretical study on novel nitrogen-rich energetic compounds of bis(amino)-azobis(azoles) with tetrazene unit

Zeng

Zhang

et al. 2012

J Mol Model

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Six stereoisomers of 5,5'-bis(amino)-1,1'-azobis (tetrazoles) and 30 other structures, including all possible bis(amino)-azobis(azoles) with an N−N0N−N unit, were designed. The molecular geometries were fully optimized at the DFT-B3LYP level with the 6-31++g (d, p) basis set. From the absence of any imaginary frequency in the infrared vibration frequency spectrum, it is predicted that all these studied structures may exist in stable forms. The results of the total energies of the stereoisomers of 5,5'-bis(amino)-1,1'-azobis(tetrazoles) indicate that the two symmetric trans-form structures are more likely to exist than the other four. The pyrolysis process, chemical stability and molecular electrostatic potential were studied via the investigation of their electronic structure. Heats of formation (HOFs) were calculated using the atomization energy method based on the results of the harmonic vibration frequencies, and a linear relationship was found between the HOF and nitrogen chain or nitrogen content. Densities of the title compounds were predicted with the Monte Carlo method. Finally, according to the results of the calculated HOFs and densities, the explosive parameters of these compounds were calculated using the Kamlet−Jacobs formula. 5,5'-Bis(amino)-1,1'-azobis(tetrazoles) and its isomer 5,5'-bis (amino)-2,2'-azobis(tetrazoles) may have potential for use as energetic compounds.

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Energetic Nitrogen‐Rich Derivatives of 1,5‐Diaminotetrazole

Abstract: High‐energy‐density materials can be obtained by reaction of monosubstituted hydrazines with cyanogen azide to generate 1,5‐diaminotetrazole derivatives. Azidohydrazones are postulated as intermediates in this reaction (see scheme).

Cited by 152 publications

References 26 publications

Application of Primary Allylamines from Morita–Baylis–Hillman Adducts: Cyanogen Azide Mediated Synthesis of Substituted 5‐Aminotetrazoles and Their Attempted Transformation into Tetrazolo[1,5‐a]pyrimidinones

Application of Primary Allylamines from Morita–Baylis–Hillman Adducts: Cyanogen Azide Mediated Synthesis of Substituted 5‐Aminotetrazoles and Their Attempted Transformation into Tetrazolo[1,5‐a]pyrimidinones

Synthesis, Structure, and Energetic Properties of 1,5‐Diaminotetrazolium Sulfate Salts

Theoretical study on novel nitrogen-rich energetic compounds of bis(amino)-azobis(azoles) with tetrazene unit

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