Progress in 1,2,3,4-Tetrazine Chemistry

Churakov, A. M.; Tartakovsky, Vladimir A.

doi:10.1021/cr020094q

Cited by 165 publications

(97 citation statements)

References 41 publications

(164 reference statements)

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“…In order to improve the energetic properties of tetra zoles, several recently published studies showed that introduction of N oxides yields compounds with even higher densities and stabilities, lower sensitivities and better oxygen balances. 2,7,11 Combining these principles with practical considerations in mind, a simple and secure synthetic pathway to the high per forming energetic material dihydroxylammonium 5,5 0 biste trazole 1,1 0 diolate (TKX 50) was devised.…”

Section: Introductionmentioning

confidence: 99%

Pushing the limits of energetic materials – the synthesis and characterization of dihydroxylammonium 5,5′-bistetrazole-1,1′-diolate

Fischer¹,

Fischer²,

Klapötke³

et al. 2012

J. Mater. Chem.

647

553

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The safe preparation and characterization (XRD, NMR and vibrational spectroscopy, DSC, mass spectrometry, sensitivities) of a new explosive dihydroxylammonium 5,5 0 bistetrazole 1,1 0 diolate (TKX 50) that outperforms all other commonly used explosive materials is detailed. While much publicized high performing explosives, such as octanitrocubane and CL 20, have been at the forefront of public awareness, this compound differs in that it is simple and cheap to prepare from commonly available chemicals. TKX 50 expands upon the newly exploited field of tetrazole oxide chemistry to produce a material that not only is easily prepared and exceedingly powerful, but also possesses the required thermal insensitivity, low toxicity, and safety of handling to replace the most commonly used military explosive, RDX (1,3,5 trinitro 1,3,5 triazacyclohexane). In addition, the crystal structures of the intermediates 5,5 0 bistetrazole 1,1 0 diol dihydrate, 5,5 0 bistetrazole 1,1 0 diol dimethanolate and dimethylammonium 5,5 0 bistetrazole 1,1 0 diolate were determined and presented.

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Section: Introductionmentioning

confidence: 99%

Pushing the limits of energetic materials – the synthesis and characterization of dihydroxylammonium 5,5′-bistetrazole-1,1′-diolate

Fischer¹,

Fischer²,

Klapötke³

et al. 2012

J. Mater. Chem.

647

553

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“…The N-oxide linkage is formally a coordinate covalent bond in which both electrons are provided by the nitrogen. In addition to being a source of oxygen, there is evidence that it somewhat counters the destabilizing effect of nitrogen catenation [15,16,50,51].…”

mentioning

confidence: 99%

“…With respect to comparing the effects of a single NO 2 group vs. a single N + → O − linkage, which is our primary purpose in this work, the data in Tables 5 and 6 An advantage of N-oxides that should be noted is that the N + → O − linkage somewhat mitigates the destabilization associated with nitrogen catenation [15,16,50,51].…”

mentioning

confidence: 99%

Nitro Groups vs. N-Oxide Linkages: Effects Upon Some Key Determinants of Detonation Performance

Politzer¹,

Murray²

2017

Cent. Eur. J. Energ. Mater.

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Abstract:Increasing the nitrogen/carbon ratios in the molecular frameworks of C,H,N,O explosives has attracted considerable attention because it tends to result in more positive heats of formation and often greater densities. In conjunction with this, there has been a growing interest in N-oxide linkages,, as another source of oxygen in these compounds, in addition to or even possibly replacing NO2 groups. In this study, for a series of polyazines and polyazoles, we have compared the effects of introducing a single N-oxide linkage or NO2 group upon key properties that affect detonation velocity and detonation pressure. We found that: (1) The heats of formation per gram of compound, which is what is relevant for this purpose, are almost always higher for the N-oxides. (2) The nitro derivatives have greater densities and detonation heat releases. In relation to the latter, it must be kept in mind that increasing detonation heat release tends to be accompanied by increasing sensitivity. (3) The N-oxides produce more moles of gaseous detonation products per gram of compound.

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“…A whole chapter is devoted to 1,2,4,5-tetrazine in Comprehensive Heterocyclic Chemistry II [8]. The chemistry of 1,2,3,4-tetrazines has recently been updated in Chemical Reviews [44].…”

Section: Tetrazinesmentioning

confidence: 99%

“…Tetrazines have been less studied than triazines since there are fewer known examples [44]. The three possible isomers of tetrazine are known and numbered as indicated in Figure 20.1.…”

Section: Introductionmentioning

confidence: 99%