Computational study of the structures and properties of aminonitroethane molecules

Mathews, Kelly Y.; Ball, David W.

doi:10.1016/j.theochem.2009.02.004

Cited by 5 publications

(4 citation statements)

References 19 publications

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“…The FOX-7 belongs to the second category, where the molecules should contain a sufficient number of oxygen atoms. Therefore one of the principal characteristics is oxygen balance = OB%) [73][74][75]. This is a dimensionless quantity (in %) expressing the number of oxygen atoms in the molecule related to their ideal number necessary for complete oxidation of the rest of the molecule.…”

Section: Energetic Propertiesmentioning

confidence: 99%

“…The negative value of the OB points to the lack of bound oxygen in the molecule. The estimation of the OB value is possible from the chemical formula of the energetic material containing only carbon, hydrogen, nitrogen and oxygen (C c H h N n O o ) using the following equation [73]:…”

Section: Energetic Propertiesmentioning

confidence: 99%

“…Most, if not all, exist as sheets of molecules with strong intermolecular hydrogen bonding between vicinal N-H and N-O groups. For various aminonitroethanes and triaminotrinitroethanes [73] the calculations of minimum-energy geometry were performed.…”

Section: Properties Of Isomeric and Relative Com-pounds To Fox-7mentioning

confidence: 99%

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2,2-Dinitroethene-1,1-Diamine

Šimková¹,

Liška²,

Ludvı́k³

2011

COC

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2,2-Dinitroethene-1,1-diamine (FOX-7) is a compound synthesized in 1998 with a simple structure but very unusual properties. One part of the molecule bears two geminal electron-withdrawing nitro groups as a strong oxidation center and the opposite part is represented by two electron-donating amino groups. This combination creates a so called push-pull effect of electrons. The electron distribution is unbalanced enabling intramolecular electron transfer reactions, what is typical for energetic material. Many studies appeared during last decade dealing with synthesis, physical properties, solubility, spectroscopic properties, acidobasic and redox properties, X-ray structure studies, reactivity, thermochemical properties, analytical reactions, quantum chemical calculations, energetic properties etc. The presented review article gives an overview of the papers devoted to the title compound.

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Section: Energetic Propertiesmentioning

confidence: 99%

Section: Energetic Propertiesmentioning

confidence: 99%

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2,2-Dinitroethene-1,1-Diamine

Šimková¹,

Liška²,

Ludvı́k³

2011

COC

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“…The discovery of FOX‐7 (1,1‐diamino‐2,2‐dinitroethylene) in 1998 was a reminder that there are still new high energy‐density substances based on small molecule backbones. In the past, we have reported on similar aminonitro derivatives based on acetylene, ethane, and cyclopropane as variations on the FOX‐7 theme.…”

Section: Introductionmentioning

confidence: 99%

Small Organic Azides as High Energy Materials: Perazidoacetylene, ‐ethylene, and ‐allene

Martin

Ball

2018

ChemistrySelect

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Compounds containing the azide group are already being used as primary explosives or energetic polymers/plasticizers. Here we present a short survey of the energy content of three small organic molecules that have been fully derivatized by N3 groups. Calculated thermodynamic and molecular properties indicate that their specific enthalpies of decomposition and combustion are in the range of those for current high energy‐density materials.

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Electrochemically triggered degradation of energetic material FOX‐7 (2,2‐dinitroethene‐1,1‐diamine) — Structural, redox, and spectrometric characterization in solution

Šimková

Ludvı́k

2020

J of Physical Organic Chem

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This work represents systemati11c electrochemical and spectrometric characterization of 2,2‐dinitroethene‐1,1‐diamine, the energetic material (explosive) known as FOX‐7, in aqueous as well as various organic solvents. On the basis of results obtained from combination of electrochemistry with ultraviolet‐visible–near‐infrared (UV‐vis‐NIR), infrared (IR), nuclear magnetic resonance (NMR), electron paramagnetic resonance (EPR), mass spectrometry (MS), gas chromatography (GC), and high‐performance liquid chromatography (HPLC) methods, the actual structure of FOX‐7 in various media was revealed, its reducibility was described, and radical intermediates as well as most of the products were intercepted and identified. Instead of expected cathodic reduction of the dinitro derivative, electrochemically initiated spontaneous degradation accompanied by release of gaseous products in all media was found.

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Computational study of the structures and properties of aminonitroethane molecules

Cited by 5 publications

References 19 publications

2,2-Dinitroethene-1,1-Diamine

2,2-Dinitroethene-1,1-Diamine

Small Organic Azides as High Energy Materials: Perazidoacetylene, ‐ethylene, and ‐allene

Electrochemically triggered degradation of energetic material FOX‐7 (2,2‐dinitroethene‐1,1‐diamine) — Structural, redox, and spectrometric characterization in solution

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