Ssynthesis of Octahydro-2,5-bis(nitroimino)imidazo[4,5-d]imidazole

Kony, Michael; Dagley, Ian J.

doi:10.3987/com-93-6597

Cited by 13 publications

(13 citation statements)

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“…The title compound, (I), is a nitramine explosive with unout melting at 599 K (Kony & Dagley, 1994). The predicted density for this compound (assuming all the N--H protons are hydrogen bonded) is 1.84 Mg m -3 (Cichra, Holden & Dickinson, 1980), which is in agreement with the calculated crystal density.…”

Section: Commentsupporting

confidence: 73%

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A high-density thermally stable explosive: octahydro-2,5-bis(nitroimino)imidazo[4,5-d]imidazole

Flippen‐Anderson¹,

Kony²,

Dagley³

1994

Acta Crystallogr C

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The title compound, C4H6N804, has a calculated crystal density of 1.84 Mg m -3. It lies on a crystallographic twofold axis passing through the midpoint of the C4--C4 i bond [symmetry code: (i) -x, -y, z]. The five-membered ring has a flattened envelope conformation with C4 lying 0.17 A out of the plane of the other four atoms. The geometry at one of the ring N atoms (N 1) is planar and that at the other (N3) is slightly pyramidal. There is a cis

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Section: Commentsupporting

confidence: 73%

“…The compound was prepared from the hydrochloride salt of octahydro-5-imino-2-nitroiminoimidazo[4,5-d]imidazole using the nitration procedure of Kony & Dagley (1994). SHELXL (Sheldrick, 1994) Data collection, cell refinement, data reduction, structure solution and molecular graphics: SHELXTL-Plus (Sheldrick, 1992).…”

Section: Methodsmentioning

confidence: 99%

A high-density thermally stable explosive: octahydro-2,5-bis(nitroimino)imidazo[4,5-d]imidazole

Flippen‐Anderson¹,

Kony²,

Dagley³

1994

Acta Crystallogr C

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“…Despite the success of chloride assisted nitramine formation from secondary amines, very little work has appeared in the open literature since the late 1940s. An online search of Chemical Abstracts revealed only a handful of references to chloride assisted nitrolysis reactions (5,6) , none of which concerned nitramine formation via nitrolysis of tertiary amines. In this paper an alternative synthetic pathway to the patented insensitive energetic nitramine 2-nitroimino-5-nitrohexahydro-1,3,5-triazine (7) is presented.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2-Nitroimino-5-Nitrohexahydro-1,3,5-Triazinevia Chloride-Assisted Nitrolysis of a Tertiary Amine

Cliff¹,

Dagley²,

Parker³

et al. 1998

Propellants, Explosives, Pyrotechnics

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An alternative synthesis of the insensitive energetic nitramine 2-nitroimino-5-nitrohexahydro-1,3,5-triazine (1) via nitrolysis of a tertiary amine is presented. Nitration of the tertiary amine precursor (2) is effected by chloride-assisted elimination of the tert-butyl moiety, with the chloramine presumably formed as an intermediate. The reaction fails to proceed in the absence of chloride at 0 C, however, its inclusion in the reaction system leads to a smooth conversion to (1) under mild nitrating conditions, which can be scaled up to yield multigram quantities. This is the ®rst known example of a chlorideassisted nitrolysis of a tertiary amine to appear in the open literature.

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“…In this work, crystal structure, thermal behavior, thermodynamic properties, electronic density, nature bond orbital charges, frontier molecular orbital, density of state and electrostatic potentials were investigated in order to give a better understanding of the chemical and physical properties of an important energetic intermediate 7-imino-3-nitroimino-2,4,6,8-tetraazabicyclo[3.3.0]octane hydrochloride (Scheme 2). [10] The measured or calculated data may shine light on the exploring of explosives and provide theoretical support for synthesizing these energetic materials in lab.…”

Section: Introductionmentioning

confidence: 99%

Crystal Structure and Properties of 7‐Imino‐3‐Nitroimino‐2,4,6,8‐Tetraazabicyclo[3.3.0]Octane Hydrochloride

Jin

2016

Zeitschrift anorg allge chemie

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Abstract. The chemical and physical properties of the energetic intermediate 7-imino-3-nitroimino-2, 4,6,8-tetraazabicyclo[3.3.0]-octane hydrochloride (compound A) were investigated. The crystal structure and thermal behavior were measured by X-ray diffraction and TG-DTG-DSC coupling system, respectively. The electronic structure was also studied by electronic density, nature bond orbital charges, frontier molecular orbital, density of state, and electrostatic potentials. Compound A crystallizes orthorhombic in space group Pna2 1 . Thermodynamic properties indicate that it has moderate thermal sta-

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Ssynthesis of Octahydro-2,5-bis(nitroimino)imidazo[4,5-d]imidazole

Cited by 13 publications

References 0 publications

A high-density thermally stable explosive: octahydro-2,5-bis(nitroimino)imidazo[4,5-d]imidazole

A high-density thermally stable explosive: octahydro-2,5-bis(nitroimino)imidazo[4,5-d]imidazole

Synthesis of 2-Nitroimino-5-Nitrohexahydro-1,3,5-Triazinevia Chloride-Assisted Nitrolysis of a Tertiary Amine

Crystal Structure and Properties of 7‐Imino‐3‐Nitroimino‐2,4,6,8‐Tetraazabicyclo[3.3.0]Octane Hydrochloride

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