The preparation and characterization of guanylurea nitrate and perchlorate salts

Klapötke, Thomas M.; Sabaté, Carles Miró

doi:10.1002/hc.20419

Cited by 21 publications

(11 citation statements)

References 18 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Single crystals of compounds 4 , 7 19, 8a and 10 , suitable for X‐ray diffraction analysis, were grown as described in the experimental section. The X‐ray crystallographic data sets were collected with an Oxford Diffraction Xcalibur 3 diffractometer equipped with a CCD detector using the CrysAlis CCD software 26.…”

Section: Resultsmentioning

confidence: 99%

“…The crystal structure of the perchlorate salt ( 7 ) has been previously reported in our group 19 and is only showed here for comparison purposes. Figure 2 shows the asymmetric unit of the compound, where the lone pair of the NH 2 nitrogen atom (N1) shows delocalization over to the carbonyl group, as reflected by a substantially shorter C1–N1 distance (~1.33 Å) in comparison to the C1–N2 bond (~1.40 Å).…”

Section: Resultsmentioning

confidence: 99%

“…Surprisingly, regardless of the potential of guanylurea chloride monohydrate 16 and guanylurea sulfate ( 5 ) as starting materials for the synthesis of energetic compounds and the interesting energetic properties of the dinitramide salt, the latter remains as the only report of a guanylurea salt, which has been considered for energetic applications. The nitrate salt ( 6 ) had been either only mentioned 17 or described in the non‐international literature 18 prior to our studies 19. Thus, we decided to investigate the potential of the GU + cation to form energetic salts in combination with highly endothermic anions (N 3 – , [N 4 C–NO 2 ] – , [N 4 C–NH 2 ] – and [N 4 C–N=N–CN 4 ] 2– ) and oxygen‐rich anions ([N 4 C–NO 2 ] – and picrate).…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Low Energy Monopropellants Based on the Guanylurea Cation

Klapötke

Sabaté

2009

Zeitschrift anorg allge chemie

View full text Add to dashboard Cite

Reaction of cyanoguanidine (3) with hydrochloric, sulfuric, nitric or perchloric acids yielded guanylurea chloride (4), sulfate (5), nitrate (6) and perchlorate (7). Compounds 4 and 5 reacted further to form a new family of energetic salts based on the guanylurea cation and azide (8a), 5-nitrotetrazolate (9), 5-aminotetrazolate (10), picrate (11) and 5,5'-azotetrazolate (12a) anions. The water of hydration in compounds 8a and 12a was eliminated by heating under vacuum yielding the anhydrous salts 8b and 12b. All materials were characterized by means of elemental analysis, mass spectrometry (MS) as well as vibrational (IR, Raman) and NMR ( 1 H, 13 C, 14/15 N and 35 Cl) spectroscopy. Additionally, the crystal structures of 4, 7, 8a and 10 were determined by low temperature X-ray measurements (4, 7 and 8a: Monoclinic, P2 1 /c; 10: Monoclinic, P2 1 ). The thermal behavior of 6-12 was assessed by DSC measurements and their heats of formation were cal-* Prof. Dr. T. M. Klapötke

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Low Energy Monopropellants Based on the Guanylurea Cation

Klapötke

Sabaté

2009

Zeitschrift anorg allge chemie

View full text Add to dashboard Cite

show abstract

“…Nitrogen-rich compounds are candidates for replacing currently used energetic materials (propellants, explosives, pyrotechnics) with "green" replacements because the main combustion/detonation product is harmless molecular nitrogen. [4][5][6] The unique stability of dinitrogen that arises from its strong, short, triple bond means that the decomposition of high-nitrogen compounds with the formation of nitrogen gas is highly favored energetically, thus making nitrogen-rich compounds one intensely pursued strategy in the design of energetic materials. [7][8][9] For a nitrogen-rich material to find practical use as a high explosive, it needs to possess high thermal and mechanical stabilities while concurrently satisfying the demand for ever higher-performing materials.…”

Section: Introductionmentioning

confidence: 99%

The Taming of CN₇⁻: The Azidotetrazolate 2‐Oxide Anion

Klapötke

Piercey

Stierstorfer

2011

Chemistry A European J

Self Cite

117

View full text Add to dashboard Cite

The highly sensitive 5-azidotetrazolate anion was oxidized to its corresponding N-oxide by aqueous oxidation in a buffered oxone solution to the azidotetrazolate 2-oxide anion. After acidic extraction and neutralization with ammonia, the ammonium salt was isolated. Several energetic salts of this novel anion were prepared from the ammonium salt, and in all cases were found to be of lower sensitivity than the corresponding 5-azidotetrazolate salt while still being highly sensitive towards mechanical stimuli. Explosive performances (detonation velocity, detonation pressure) of applicable salts were also found to be higher than the non-N-oxide variants. Preparation of the free acid 2-hydroxy-5-azidotetrazole was achieved by protonation of the anion and identified by NMR spectroscopy, whereas the majority of the azidotetrazolate 2-oxide salts have unequivocal crystallographic proof.

show abstract

“…Tetrazole-based energetic compounds as a class of nitrogenrich materials with interesting properties have caught the attention of chemists, physicists, and material scientists for their potential application in gas generators [1,2], blowing agents [3][4][5][6], primary explosives [7], or ingredients in pyrotechnic and propellant mixtures [8]. They are also very popular in coordination chemistry as ligands through the four nitrogen electrondonating atoms that allow them to serve as either multidentate or bridging building blocks in supramolecular assemblies, medicinal chemistry and various materials science applications as a metabolically stable surrogate for a carboxylic acid group [9,10].…”

Section: Introductionmentioning

confidence: 99%