Synthesis, single crystal structure and performance of N-substituted derivatives of dinitroimidazole

Hou, Kehui; Ma, Congming; Liu, Zuliang

doi:10.1039/c3nj00521f

Cited by 18 publications

(4 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…With the increase of the number of amino groups, the decomposition temperatures of these compounds gradually decrease. A similar phenomenon was also observed in polynitro(amino)benzene-substituted derivatives of dinitroimidazoles …”

Section: Resultssupporting

confidence: 76%

“…A similar phenomenon was also observed in polynitro(amino)benzene-substituted derivatives of dinitroimidazoles. 22 As shown above, with the increase in the number of NH 2 group, the crystal stability is actually improved with increased melting points due to increased hydrogen bonds. The melting point of 1c is 29 °C higher than that of 1a with a reduced enthalpy of −61.3 J g −1 , even it is not so significant from 1a to 1b, due to the increased asymmetry of the molecule.…”

Section: Resultsmentioning

confidence: 82%

“…However, constrained by elemental composition, most of the polynitrophenyl compounds are unable to meet the future requirements due to their relatively low energy density. − In recent years, the combination of nitrogen heterocycles and polynitrophenyl skeleton has appeared as an effective means for the design of novel HREs (Scheme ). Owing to their activity toward nucleophiles, a number of nitrogen heterocycles such as imidazole, triazene, pyrazole, and triazole have been utilized to react with chloronitroarenes to yield highly thermostable EMs. − Although the inclusion of polynitrogen heterocycles into the conjugated system improves the heat of formation, it also results in reduced oxygen balance. As an important nitrogen heterocyclic core unit, 1,2,5-oxadiazole (furazan), 1,2,5-oxadiazole N -oxide (furoxan), and 1,2,4-oxadiazole have attracted wide attention due to their high heat of formation and good oxygen balance. − Klapötke et al reported the synthesis and performance of a novel HRE 5,5′-bis(2,4,6-trinitrophenyl)-2,2′-bi(1,3,4-oxadiazole) (TKX-55) in 2016 .…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Highly Thermostable Insensitive Energetic Polynitrophenyl-Substituted Furazan (Furoxan)-Annelated Azepines

Liu¹,

Xiao

Duan³

et al. 2020

ACS Appl. Energy Mater.

View full text Add to dashboard Cite

Achieving high thermal stability and low mechanical sensitivity are two major goals in the development of energetic compounds. Six highly stable insensitive polynitrophenyl-substituted furazan (furoxan)-annelated azepines have been prepared and characterized in this work. All the involved compounds were characterized by 1H and 13C NMR spectroscopy, IR spectroscopy, and elemental analysis, and four of them were further supported by single-crystal X-ray diffraction investigations. Moreover, their thermal stabilities and mechanical sensitivities were evaluated. All energetic compounds exhibited excellent thermal stabilities with decomposition temperatures ranging from 290 to 333 °C. Compounds 1c and 2c exhibit extremely low mechanical sensitivity (IS >40 J and FS > 360 N). Based on experimental densities and calculated heat of formation, the detonation velocities and pressures for the energetic compounds were calculated using EXPLO5 (V6.04) with the corresponding results in the range of 26.4 to 29.9 GPa and 7979 m s–1 to 8356 m s–1. The detailed study based on Hirshfeld surfaces and electrostatic potential (ESP) analysis was used to illustrate the relationship between molecular structures and sensitivity of these compounds. The comprehensive performances of these materials are superior to those of the widely used heat-resistant explosive HNS (2,2′,4,4′,6,6′-hexanitrostilbene).

show abstract

Section: Resultssupporting

confidence: 76%

Section: Resultsmentioning

confidence: 82%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Highly Thermostable Insensitive Energetic Polynitrophenyl-Substituted Furazan (Furoxan)-Annelated Azepines

Liu¹,

Xiao

Duan³

et al. 2020

ACS Appl. Energy Mater.

View full text Add to dashboard Cite

show abstract

“…The sensitivity of this compound was not reported. Recently,4 ,5-DNI and 2,4-DNI were allowed to condense with picryl chloride, 3-chloro-2,4,6-trinitrobenzenamine and 5-chloro-1,3-diamino-2,4,6-trinitrobenzene, to yield several new insensitive energetic compounds [ 76].T he densities ranged from 1.748 gcm À3 to 1.842 gcm À3 and decomposition points ranged from 237 8Ct o2 82 8C. The most interesting compoundsw ere 1-(3,5-diamino-2,4,6-trinitrophenyl)-2,4-dinitroimidazole (6)a nd 1-(3-amino-2,4,6-trinitrophenyl)-4,5-dinitroimidazole (7), both with ah igh-degreeo fh ydrogen bondingb ut with aw avelike crystalp acking pattern.…”

Section: Small-ring Heterocyclic Insensitive Energetic Compoundsmentioning

confidence: 99%

A Comparison of the Structure, Synthesis, and Properties of Insensitive Energetic Compounds

Pagoria

2016

Propellants Explo Pyrotec

104

View full text Add to dashboard Cite

1IntroductionIn general, highe xplosivesa re categorized as primary,s econdary,a nd tertiary explosives, basedo nt heir sensitivity to mechanical insults. Primarye xplosivesa re very sensitive to mechanical and electricali nitiation and are used as initiating explosives in an explosivet rain. Secondary explosives are less sensitivet om echanical stimuli, although in many cases can still be somewhat sensitive materials. Te rtiary explosives are generallyv ery insensitivee xplosivesv ery often consistingo fa no xidizer and af uel, and are generallyu sed in mining. Subsets of secondary explosives are insensitive energetic compoundso rm aterials. Insensitive energetic compounds are defined as compoundst hat have relatively benign responses to externali nsults such as impact, shock, spark, friction, and heat. Understandingt he various factors that affectt he sensitivity of energetic compoundst ov arious mechanical insults plays an important role in the design of new,i nsensitive, and thermally stable higher-performance energetic materials. While there have been several excellent reviewsa nd books on new energetic compounds in the past 15 years [1-7],t his review will concentrate on insensitivee nergetic compounds. Also this paper will concentrate on insensitive energeticc ompounds and not discuss insensitivee nergetic formulationso rm ixtures or engineering methods to decrease sensitivity.Althoughs park and friction sensitivity are important, impact, shock, and thermal stabilitya re the most commonly used measurements to determine the relatives ensitivity of ag iven compoundc ompared to knowns tandards. In this paper the term insensitivity will refer mainly to impact and thermal sensitivity.I mpact sensitivity is generally measured by using a" drop hammer" impact machine, in which an anvil of ag iven weight (generally 5kg) is allowed to impact as mall sample (ca. 35 mg) of an explosive and the responsei sr ecorded. Historically,d rop hammer results (Dh 50 or H 50 )w ere reported as the height, at which there is a5 0% probabilityo fi gnition. In recenty ears, some authors are convertingt he recorded drop hammer heights to Joules and are reporting the energy required at which there is a5 0% probability of ignition. Thermal stabilitym ay be measured using several methods including differential scanning calorimetry (DSC), differential thermala nalysis (DTA), chemical reactivity test (CRT), vacuum stability test (VTS), slow cook-off test, and fast cook-off test.The industry standardf or an insensitive energetic compound is 1,3,5-triamino-2,4,6-trinitrobenzene (TATB), ar easonably powerful explosive, whose response to shock, thermal, impact and friction insultsi ss ignificantly more benign than that of any other knownm aterial of comparable energy [8,9].T his "enhanced" insensitivity of TATB has led to as ignificant amount of studies on how various physical properties including molecular structure,c rystal structure, and crystal packing of TATB contributes to its "enhanced" insensitivity,a nd how these physical properties c...

show abstract

ChemInform Abstract: Synthesis, Single Crystal Structure and Performance of N‐Substituted Derivatives of Dinitroimidazole.

Hou

Liu

2014

ChemInform

View full text Add to dashboard Cite

Synthesis, Single Crystal Structure and Performance of N-Substituted Derivatives of Dinitroimidazole. -The title compounds are synthesized for the application as energetic materials via a simple and scalable method without complicated purification procedures. Their experimental densities range between 1.75 -1.84 g cm -3 . The derivatives bearing two amino groups show higher densities. -(HOU, K.; MA, C.; LIU*, Z.; New J. Chem. 37 (2013) 9, 2837-2844, http://dx.

show abstract

Synthesis, single crystal structure and performance of N-substituted derivatives of dinitroimidazole

Cited by 18 publications

References 20 publications

Highly Thermostable Insensitive Energetic Polynitrophenyl-Substituted Furazan (Furoxan)-Annelated Azepines

Highly Thermostable Insensitive Energetic Polynitrophenyl-Substituted Furazan (Furoxan)-Annelated Azepines

A Comparison of the Structure, Synthesis, and Properties of Insensitive Energetic Compounds

ChemInform Abstract: Synthesis, Single Crystal Structure and Performance of N‐Substituted Derivatives of Dinitroimidazole.

Contact Info

Product

Resources

About