Tetraaminoethylene
Encyclopedia
Tetraaminoethylene is a hypothetical organic compound
with formula C2N4H8 or (H2N-)2C=C(-NH2)2. Like all geminal
polyamine
s, this compound has never been synthesised and is believed to be extremely unstable.
However, there are many stable compounds that can be viewed as derivatives of tetraaminoethylene, with various organic functional groups substituted for some or all hydrogen atoms. These compounds, which have the general formula (R2N)2C=C(NR2)2, are collectively called tetraaminoethylenes.
Tetraaminoethylenes are important in organic chemistry
as dimers of diaminocarbenes, a type of stable carbene with the general formula (R2N-)2C:.
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
with formula C2N4H8 or (H2N-)2C=C(-NH2)2. Like all geminal
Geminal
In chemistry, the term geminal refers to the relationship between two functional groups that are attached to the same atom...
polyamine
Polyamine
A polyamine is an organic compound having two or more primary amino groups .This class of compounds includes several synthetic substances that are important feedstocks for the chemical industry, such as ethylene diamine , 1,3-diaminopropane , and hexamethylenediamine...
s, this compound has never been synthesised and is believed to be extremely unstable.
However, there are many stable compounds that can be viewed as derivatives of tetraaminoethylene, with various organic functional groups substituted for some or all hydrogen atoms. These compounds, which have the general formula (R2N)2C=C(NR2)2, are collectively called tetraaminoethylenes.
Tetraaminoethylenes are important in organic chemistry
Organic chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, composition, reactions, and preparation of carbon-based compounds, hydrocarbons, and their derivatives...
as dimers of diaminocarbenes, a type of stable carbene with the general formula (R2N-)2C:.
Reactions
- Tetraaminoethylenes react with acids to give formamidiniumFormamidiniumFormamidinium cations are positively charged organic chemical compounds which can be represented by the chemical formula [R2N-CH=NR2]+.-Chemical applications:...
salts.
- Tetraaminoethylenes react with oxygenOxygenOxygen is the element with atomic number 8 and represented by the symbol O. Its name derives from the Greek roots ὀξύς and -γενής , because at the time of naming, it was mistakenly thought that all acids required oxygen in their composition...
to give ureaUreaUrea or carbamide is an organic compound with the chemical formula CO2. The molecule has two —NH2 groups joined by a carbonyl functional group....
derivatives (R2N)2C=O. A notorious example is the spontaneous reaction of octamethyltetraminoethylene ((H3C-)2N-)2C=C(-N(-CH3)2)2 in air with emission of a green-blue light, which was used by downed US NavyUnited States NavyThe United States Navy is the naval warfare service branch of the United States Armed Forces and one of the seven uniformed services of the United States. The U.S. Navy is the largest in the world; its battle fleet tonnage is greater than that of the next 13 largest navies combined. The U.S...
pilots to signal for help in World War IIWorld War IIWorld War II, or the Second World War , was a global conflict lasting from 1939 to 1945, involving most of the world's nations—including all of the great powers—eventually forming two opposing military alliances: the Allies and the Axis...
.