Triazene, also known as triazanylene, is an unsaturated

Unsaturated compound

In organic chemistry, a saturated compound is a chemical compound that has of a chain of carbon atoms linked together by single bonds and has hydrogen atoms filling all of the other bonding orbitals of the carbon atoms. Alkanes are an example of saturated compounds...

 inorganic compound

Inorganic compound

Inorganic compounds have traditionally been considered to be of inanimate, non-biological origin. In contrast, organic compounds have an explicit biological origin. However, over the past century, the classification of inorganic vs organic compounds has become less important to scientists,...

 having the chemical formula N

Nitrogen

Nitrogen is a chemical element that has the symbol N, atomic number of 7 and atomic mass 14.00674 u. Elemental nitrogen is a colorless, odorless, tasteless, and mostly inert diatomic gas at standard conditions, constituting 78.08% by volume of Earth's atmosphere...

₃H

Hydrogen

Hydrogen is the chemical element with atomic number 1. It is represented by the symbol H. With an average atomic weight of , hydrogen is the lightest and most abundant chemical element, constituting roughly 75% of the Universe's chemical elemental mass. Stars in the main sequence are mainly...

₃. It has one double bond

Covalent bond

A covalent bond is a form of chemical bonding that is characterized by the sharing of pairs of electrons between atoms. The stable balance of attractive and repulsive forces between atoms when they share electrons is known as covalent bonding....

, and is the second simplest member of the azene class of hydronitrogen compounds, and is not found in nature. It is also the name given to the functional group

Functional group

In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. The same functional group will undergo the same or similar chemical reaction regardless of the size of the molecule it is a part of...

 consisting of an amine

Amine

Amines are organic compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines,...

 directly bonding to an azo

Azo compound

Azo compounds are compounds bearing the functional group R-N=N-R', in which R and R' can be either aryl or alkyl. IUPAC defines azo compounds as: "Derivatives of diazene , HN=NH, wherein both hydrogens are substituted by hydrocarbyl groups, e.g. PhN=NPh azobenzene or diphenyldiazene." The more...

 group, i.e. with the linkage R¹R²N-N=NR³ where R¹, R² and R³ are substituents. The functional group is also called a diazoamino group (but only one of the two substituents R¹ and R³ may be hydrogen) because it is related to a diazo

Diazo

Diazo refers to a type of organic compound called diazo compound that has two linked nitrogen atoms as a terminal functional group. The general formula is R2C=N2. The simplest example of a diazo compound is diazomethane...

 group.

Properties

At room temperature

Room temperature

-Comfort levels:The American Society of Heating, Refrigerating and Air-Conditioning Engineers has listings for suggested temperatures and air flow rates in different types of buildings and different environmental circumstances. For example, a single office in a building has an occupancy ratio per...

, triazene is a gas, and as with many other azenes, it is also coloured with a strong and unpleasant smell. Triazene has a higher density and boiling point than diazene

Diazene

Diazene, also called diimine or diimide, is a compound having the formula 2. It exists as two geometric isomers, E and Z. Diazene is also the parent member of the entire class of azo compounds with the formula 2, where R is an organyl group...

 due to its greater size. It has a slightly lower boiling point than triazane and is thus more volatile

Volatility (chemistry)

In chemistry and physics, volatility is the tendency of a substance to vaporize. Volatility is directly related to a substance's vapor pressure. At a given temperature, a substance with higher vapor pressure vaporizes more readily than a substance with a lower vapor pressure.The term is primarily...

. It has strong polar bonds

Polar bond

In chemistry, a polar bond is a type of covalent bond between two atoms or more in which electrons are shared unequally. Because of this, one end of the molecule has a slight, relative negative charge and the other a slight, relative positive charge...

, and the molecule has a large dipole moment

Bond dipole moment

The bond dipole moment uses the idea of electric dipole moment to measure the polarity of a chemical bond within a molecule. The bond dipole μ is given by:\mu = \delta \, d....

 due to its reduced symmetry.

Triazene has the same empirical formula as cyclotriazane but their atoms are connected in different ways, making these molecules structural isomers.

Production

To date, the only proven method to produce triazene, is the spontaneous decomposition of tetraazane into triazene and ammonia.

Derivatives

A well known example is of a triazene is diphenyl derivative, PhNH-N=NPh (m.p. 100 °C, CAS #136-35-6). It is prepared from phenyldiazonium salts and aniline

Aniline

Aniline, phenylamine or aminobenzene is an organic compound with the formula C6H5NH2. Consisting of a phenyl group attached to an amino group, aniline is the prototypical aromatic amine. Being a precursor to many industrial chemicals, its main use is in the manufacture of precursors to polyurethane...

in the presence of base:

PhN₂⁺ + PhNH₂ → PhNHN=NPh + H⁺