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 compound 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">Ammonium</span> Chemical compound

The ammonium cation is a positively charged polyatomic ion with the chemical formula NH+4 or [NH4]+. It is formed by the protonation of ammonia. Ammonium is also a general name for positively charged (protonated) substituted amines and quaternary ammonium cations, where one or more hydrogen atoms are replaced by organic or other groups.

<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 toxic unless handled in solution as, for example, hydrazine hydrate.

Unsymmetrical dimethylhydrazine (UDMH; 1,1-dimethylhydrazine, heptyl or codenamed Geptil) is a chemical compound with the formula H2NN(CH3)2 that is used as a rocket propellant. It is a colorless liquid, with a sharp, fishy, ammonia-like smell typical for organic amines. Samples turn yellowish on exposure to air and absorb oxygen and carbon dioxide. It is miscible with water, ethanol, and kerosene. In concentration between 2.5% and 95% in air, its vapors are flammable. It is not sensitive to shock. Symmetrical dimethylhydrazine (1,2-dimethylhydrazine) is also known but is not as useful. UDMH can be oxidized in air to form many different substances, including toxic ones.

<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/Russia 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. Although nitrogen is more electronegative than iodine, the compound was so named due to its analogy to the compound nitrogen trichloride.

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

Zinc chloride is the name of inorganic chemical compounds with the formula ZnCl2. It forms hydrates. Zinc chloride, anhydrous and its hydrates are colorless or white crystalline solids, and are highly soluble in water. Five hydrates of zinc chloride are known, as well as four forms of anhydrous zinc chloride. This salt is hygroscopic and even deliquescent. Zinc chloride finds wide application in textile processing, metallurgical fluxes, and chemical synthesis. No mineral with this chemical composition is known aside from the very rare mineral simonkolleite, Zn5(OH)8Cl2·H2O.

<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">Trimethylaluminium</span> Chemical compound

Trimethylaluminium is one of the simplest examples of an organoaluminium compound. Despite its name it has the formula Al2(CH3)6 (abbreviated as Al2Me6 or TMA), as it exists as a dimer. This colorless liquid is pyrophoric. It is an industrially important compound, closely related to triethylaluminium.

<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">Arsenic tribromide</span> Chemical compound

Arsenic tribromide is an inorganic compound with the formula AsBr3, it is a bromide of arsenic. Arsenic is a chemical element that has the symbol As and atomic number 33. This pyramidal molecule is the only known binary arsenic bromide. AsBr3 is noteworthy for its very high refractive index of approximately 2.3. It also has a very high diamagnetic susceptibility. It is a poisonous metalloid that has many allotropic forms: yellow and several black and gray forms (metalloids), orthorhombic prisms, colorless rhombic crystals are a few that are seen. Bromine is a halogen element with the symbol Br and atomic number 35. Diatomic bromine does not occur naturally, but bromine salts can be found in crustal rock.

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">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">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 canary yellow solid practically insoluble in water and most organic solvents, including DMF and DMSO.

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.