Triazane

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Triazane
Triazane.svg
Names
Systematic IUPAC name
Triazane [1]
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/H5N3/c1-3-2/h3H,1-2H2
    Key: PYHOFAHZHOBVGV-UHFFFAOYSA-N
  • NNN
Properties
N3H5
Molar mass 47.061 g·mol−1
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Triazane is an inorganic compound with the chemical formula NH2NHNH2 or N3H5. [2] Triazane is the third simplest acyclic azane after ammonia and hydrazine. It can be synthesized from hydrazine but is unstable and cannot be isolated in the free base form, only as salt forms such as triazanium sulfate. Attempts to convert triazanium salts to the free base release only diazene and ammonia. [3] Triazane was first synthesized as a ligand of the silver complex ion: tris(μ2-triazane-κ2N1,N3)disilver(2+).[ clarification needed ] Triazane has also been synthesized in electron-irradiated ammonia ices and detected as a stable gas-phase product after sublimation. [4]

Contents

Compounds containing the triazane skeleton

Several compounds containing the triazane skeleton are known, including 1-methyl-1-nitrosohydrazine (NH2−N(CH3)−N=O), produced from the solventless reaction of methylhydrazine (CH3NHNH2) and an alkyl nitrite (R−O−N=O):

CH3NHNH2 + RONO → NH2N(CH3)NO + ROH

1-Methyl-1-nitrosohydrazine is a colorless solid, sensitive to impact, but not to friction. It melts at 45 °C and decomposes at 121 °C.

Related Research Articles

<span class="mw-page-title-main">Ester</span> Compound derived from an acid

In chemistry, an ester is a functional group derived from an acid in which the hydrogen atom (H) of at least one acidic hydroxyl group of that acid is replaced by an organyl group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well, but not according to the IUPAC.

<span class="mw-page-title-main">Hydrazine</span> Colorless flammable liquid with an ammonia-like odor

Hydrazine is an inorganic compound with the chemical formula N2H4. It is a simple pnictogen hydride, and is a colourless flammable liquid with an ammonia-like odour. Hydrazine is highly hazardous unless handled in solution as, for example, hydrazine hydrate.

Unsymmetrical dimethylhydrazine (abbreviated as UDMH; also known as 1,1-dimethylhydrazine, heptyl or Geptil) is a chemical compound with the formula H2NN(CH3)2 that is primarily used as a rocket propellant. At room temperature, UDMH is a colorless liquid, with a sharp, fishy, ammonia-like smell typical of organic amines. Samples turn yellowish on exposure to air and absorb oxygen and carbon dioxide. It is miscible with water, ethanol, and kerosene. At concentrations between 2.5% and 95% in air, its vapors are flammable. It is not sensitive to shock.

<span class="mw-page-title-main">Dinitrogen tetroxide</span> Chemical compound

Dinitrogen tetroxide, commonly referred to as nitrogen tetroxide (NTO), and occasionally (usually among ex-USSR/Russian rocket engineers) as amyl, is the chemical compound N2O4. It is a useful reagent in chemical synthesis. It forms an equilibrium mixture with nitrogen dioxide. Its molar mass is 92.011 g/mol.

<span class="mw-page-title-main">Nitrogen triiodide</span> Chemical compound

Nitrogen triiodide is an inorganic compound with the formula NI3. It is an extremely sensitive contact explosive: small quantities explode with a loud, sharp snap when touched even lightly, releasing a purple cloud of iodine vapor; it can even be detonated by alpha radiation. NI3 has a complex structural chemistry that is difficult to study because of the instability of the derivatives.

<span class="mw-page-title-main">Azo compound</span> Organic compounds with a diazenyl group (–N=N–)

Azo compounds are organic compounds bearing the functional group diazenyl.

<span class="mw-page-title-main">Phosphonium</span> Family of polyatomic cations containing phosphorus

In chemistry, the term phosphonium describes polyatomic cations with the chemical formula PR+
4
. These cations have tetrahedral structures. The salts are generally colorless or take the color of the anions.

<span class="mw-page-title-main">Perbromate</span> Ion

In chemistry, the perbromate ion is the anion having the chemical formula BrO
4
. It is an oxyanion of bromine, the conjugate base of perbromic acid, in which bromine has the oxidation state +7. Unlike its chlorine and iodine analogs, it is difficult to synthesize. It has tetrahedral molecular geometry.

<span class="mw-page-title-main">Dimethylamine</span> Chemical compound

Dimethylamine is an organic compound with the formula (CH3)2NH. This secondary amine is a colorless, flammable gas with an ammonia-like odor. Dimethylamine is commonly encountered commercially as a solution in water at concentrations up to around 40%. An estimated 270,000 tons were produced in 2005.

<span class="mw-page-title-main">Triazene</span> Unsaturated inorganic compound of formula N₃H₃

Triazene is an unsaturated inorganic compound having the chemical formula N3H3. It has one double bond and is the second-simplest member of the azene class of hydronitrogen compounds, after diimide. Triazenes are a class of organic compounds containing the functional group −N(H)−N=N−. Triazene, possibly along with its isomer triimide (HNNHNH), has been synthesized in electron-irradiated ices of ammonia and ammonia/dinitrogen and detected in the gas phase after sublimation.

<span class="mw-page-title-main">Ammonia borane</span> Chemical compound

Ammonia borane, also called borazane, is the chemical compound with the formula H3NBH3. The colourless or white solid is the simplest molecular boron-nitrogen-hydride compound. It has attracted attention as a source of hydrogen fuel, but is otherwise primarily of academic interest.

<span class="mw-page-title-main">Sulfur tetrafluoride</span> Chemical compound

Sulfur tetrafluoride is a chemical compound with the formula SF4. It is a colorless corrosive gas that releases dangerous hydrogen fluoride gas upon exposure to water or moisture. Sulfur tetrafluride is a useful reagent for the preparation of organofluorine compounds, some of which are important in the pharmaceutical and specialty chemical industries.

Bis(trimethylsilyl)amine (also known as hexamethyldisilazane and HMDS) is an organosilicon compound with the molecular formula [(CH3)3Si]2NH. The molecule is a derivative of ammonia with trimethylsilyl groups in place of two hydrogen atoms. An electron diffraction study shows that silicon-nitrogen bond length (173.5 pm) and Si-N-Si bond angle (125.5°) to be similar to disilazane (in which methyl groups are replaced by hydrogen atoms) suggesting that steric factors are not a factor in regulating angles in this case. This colorless liquid is a reagent and a precursor to bases that are popular in organic synthesis and organometallic chemistry. Additionally, HMDS is also increasingly used as molecular precursor in chemical vapor deposition techniques to deposit silicon carbonitride thin films or coatings.

<span class="mw-page-title-main">Beryllium hydride</span> Chemical compound

Beryllium hydride is an inorganic compound with the chemical formula n. This alkaline earth hydride is a colourless solid that is insoluble in solvents that do not decompose it. Unlike the ionically bonded hydrides of the heavier Group 2 elements, beryllium hydride is covalently bonded.

<span class="mw-page-title-main">Trimethylstibine</span> Chemical compound

Trimethylstibine is an organoantimony compound with the formula Sb(CH3)3. It is a colorless pyrophoric and toxic liquid. It is synthesized by treatment of antimony trichloride and methyl Grignard reagent. It is produced by anaerobic bacteria in antimony-rich soils. In contrast to trimethylphosphine, trimethylstibine is a weaker Lewis base. It is used in the production of some III-V semiconductors.

<span class="mw-page-title-main">Dinitrogen trioxide</span> Chemical compound

Dinitrogen trioxide is the inorganic compound with the formula N2O3. It is a nitrogen oxide. It forms upon mixing equal parts of nitric oxide and nitrogen dioxide and cooling the mixture below −21 °C (−6 °F):

<span class="mw-page-title-main">Trimethylborane</span> Chemical compound

Trimethylborane (TMB) is a toxic, pyrophoric gas with the formula B(CH3)3 (which can also be written as Me3B, with Me representing methyl).

<span class="mw-page-title-main">Tetramethyldiborane</span> Chemical compound

Dimethylborane, (CH3)2BH is the simplest dialkylborane, consisting of a methyl group substituted for a hydrogen in borane. As for other boranes it normally exists in the form of a dimer called tetramethyldiborane or tetramethylbisborane or TMDB ((CH3)2BH)2. Other combinations of methylation occur on diborane, including monomethyldiborane, trimethyldiborane, 1,2-dimethylborane, 1,1-dimethylborane and trimethylborane. At room temperature the substance is at equilibrium between these forms. The methylboranes were first prepared by H. I. Schlesinger and A. O. Walker in the 1930s.

Silver hyponitrite is an ionic compound with formula Ag2N2O2 or (Ag+
)2[ON=NO]2−, containing monovalent silver cations and hyponitrite anions. It is a bright yellow solid practically insoluble in water and most organic solvents, including DMF and DMSO.

<span class="mw-page-title-main">Methyl fluoroacetate</span> Chemical compound

Methyl fluoroacetate (MFA) is an organic compound with the chemical formula FCH2CO2CH3. It is the extremely toxic methyl ester of fluoroacetic acid. It is a colorless, odorless liquid at room temperature. It is used as a laboratory chemical and as a rodenticide. Because of its extreme toxicity, MFA was studied for potential use as a chemical weapon.

References

  1. "triazane - PubChem Public Chemical Database". The PubChem Project. USA: National Center for Biotechnology Information.
  2. IUPAC Goldbook
  3. Wiberg, Holleman & Wiberg. Inorganic Chemistry. p 627. ISBN   9780123526519
  4. Förstel, Maksyutenko, Jones, Sun, Chen, Chang, & Kaiser. "Detection of the Elusive Triazane Molecule ([N
    3
    H
    5
    ]
    ) in the Gas Phase", ChemPhysChem, 2015, 16, 3139.