Energetic Nitrate, Perchlorate, Azide and Azolate Salts of Hexamethylenetetramine

Xue, Hong; Gao, Haixiang; Twamley, Brendan; Shreeve, Jean’ne M.

doi:10.1002/ejic.200600148

Cited by 58 publications

(39 citation statements)

References 66 publications

(20 reference statements)

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“…The performance of an energetic material is mainly a function of the density of the compound, its oxygen coefficient and its heat of formation; all three parameters are governed by its molecular structure. [10] The higher the nitrogen content, the higher the heat of formation, [11] which is in turn directly related to the performance of the material.…”

Section: Introductionmentioning

confidence: 99%

1,2,4‐Triazolium‐Cation‐Based Energetic Salts

Darwich

Klapötke

Sabaté

2008

Chemistry A European J

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3,4,5-Triamino-1,2,4-triazole (guanazine, 1) can be readily methylated with methyl iodide yielding methylguanazinium iodide (2). Salts containing the novel methylguanazinium cation with energetic anions were synthesised by metathesis reactions with silver azide (3), silver nitrate (4), silver perchlorate (5), sodium 5,5'-azotetrazolate (6), silver 5-nitrotetrazolate (7) and silver dinitramide (8), yielding a new family of heterocycle-based salts, which were fully characterised by analytical (mass spectrometry and elemental analysis) and spectroscopic methods (IR, Raman and NMR). In addition, the molecular structures of all compounds were confirmed by X-ray analysis, revealing extensive hydrogen-bonding in the solid state and densities between 1.399 (3) and 1.669 g cm(-3) (5). The hydrogen-bonded ring motifs are discussed in the formalism of graph-set analysis for hydrogen-bond patterns and compared to each other. Preliminary sensitivity testing of the crystalline compounds indicate surprisingly low sensitivities to both friction and impact, the highest friction and shock sensitivity being found for the perchlorate (5, 220 N) and the dinitramide (8, 20 J) salts, respectively. In addition, DSC analysis was used to assess the thermal stabilities of the compounds: 3-6 melt above 200 degrees C with concomitant decomposition, whereas 7 and 8 have clearly defined melting points at 162 and 129 degrees C, respectively, and with decomposition occurring about 30 degrees C above the melting point. Lastly all compounds have positive calculated heats of formation between 336 (4) and 4070 kJ kg(-1) (6) and calculated detonation velocities in the range between 8330 (7) and 8922 m s(-1) (6) making them of interest as new highly energetic materials with low sensitivity.

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Section: Introductionmentioning

confidence: 99%

1,2,4‐Triazolium‐Cation‐Based Energetic Salts

Darwich

Klapötke

Sabaté

2008

Chemistry A European J

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“…In order to continue efforts in this field [25][26][27][28][29], the author now report on the spectral predication of polycyclic saturated tetrazine compound. All studies have been done in this investigation by focusing on the readily available 1,2,4,5-tetrazine as starting materials as per the literature procedures [30][31][32][33][34].…”

Section: (3) (R) C (6) (R)mentioning

confidence: 99%

Unusual Investigation of Polycyclic Saturated Tetrazine: A Breakthrough to 1,2,4,5‐Tetrazine

Swain

2015

Journal of Heterocyclic Chem

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in Wiley Online Library (wileyonlinelibrary.com).The theoretical investigation of polycyclic saturated tetrazine is a novel process, and the reaction of 1,2,4,5-tetrazine with diazomethane that undergoes polymerization reaction has been studied by using a computational method, and it gives dinitrogen (N 2 ) as the major product. The spectroscopic studies, bond length, bond angle, heat of formation, and densities are measure of investigations in this communication.The theoretical evidence of the possibility to synthesize polycyclic saturated tetrazine is a major challenge for nitrogen-rich chemistry.

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“…A single crystal X-ray study was carried out on 3-azido-1, 2, 4-triazolium nitrate (38). As expected, the proton is attached to N-4 of the 1, 2, 4-triazole ring.…”

Section: Accomplishments/new Findings: a Syntheses And Thermal Propementioning

confidence: 99%

“…Compounds with positive AHf values (34,35) are highlighted (Scheme 3, Table 3). Of all the triazolium salts synthesized (36)(37)(38)(39)(40)(41)(42)(43)(44)(45)(46)(47)(48)(49)(50)(51)(52)(53)(54)(55) 3 .…”

Section: Accomplishments/new Findings: a Syntheses And Thermal Propementioning

confidence: 99%

Ionic Liquids as Energetic Materials

Shreeve¹

2007

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Energetic Nitrate, Perchlorate, Azide and Azolate Salts of Hexamethylenetetramine

Cited by 58 publications

References 66 publications

1,2,4‐Triazolium‐Cation‐Based Energetic Salts

1,2,4‐Triazolium‐Cation‐Based Energetic Salts

Unusual Investigation of Polycyclic Saturated Tetrazine: A Breakthrough to 1,2,4,5‐Tetrazine

Ionic Liquids as Energetic Materials

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