Tetraaminoethylene on:
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In
''Amines: synthesis, properties and applications''
Cambridge University Press. , 371 pages. However, there are many stable compounds that can be viewed as
Tetraaminoethylenes are important in
organic chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, J.; ...
, tetraaminoethylene is a hypothetical
A hypothesis (plural hypotheses) is a proposed explanation for a phenomenon. For a hypothesis to be a scientific hypothesis, the scientific method requires that one can test it. Scientists generally base scientific hypotheses on previous obser ...
, organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
with formula or . Like all polyamine
A polyamine is an organic compound having more than two amino groups. Alkyl polyamines occur naturally, but some are synthetic. Alkylpolyamines are colorless, hygroscopic, and water soluble. Near neutral pH, they exist as the ammonium derivatives. ...
s that are geminal
In chemistry, the descriptor geminal () refers to the relationship between two atoms or functional groups that are attached to the same atom. A geminal diol, for example, is a diol (a molecule that has two alcohol functional groups) attached to ...
, this compound has never been synthesised and is believed to be extremely unstable.Stephen A. Lawrence (2004)''Amines: synthesis, properties and applications''
Cambridge University Press. , 371 pages. However, there are many stable compounds that can be viewed as
derivatives
The derivative of a function is the rate of change of the function's output relative to its input value.
Derivative may also refer to:
In mathematics and economics
* Brzozowski derivative in the theory of formal languages
* Formal derivative, an ...
of tetraaminoethylene, with various organic functional groups
In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest ...
substituted for some or all hydrogen atoms. These compounds, which have the general formula , are collectively called tetraaminoethylenes.
:
Tetraaminoethylenes are important in organic chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, J.; ...
as dimers of diaminocarbene
A persistent carbene (also known as stable carbene) is a type of carbene demonstrating particular stability. The best-known examples and by far largest subgroup are the ''N''-heterocyclic carbenes (NHC) (sometimes called Arduengo carbenes), for ex ...
s, a type of stable carbene
A persistent carbene (also known as stable carbene) is a type of carbene demonstrating particular stability. The best-known examples and by far largest subgroup are the ''N''-heterocyclic carbenes (NHC) (sometimes called Arduengo carbenes), for ex ...
with the general formula .
Reactions
* Tetraaminoethylenes react with acids to give formamidinium salts. * Tetraaminoethylenes react withoxygen
Oxygen is the chemical element with the symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and an oxidizing agent that readily forms oxides with most elements as wel ...
to give urea
Urea, also known as carbamide, is an organic compound with chemical formula . This amide has two amino groups (–) joined by a carbonyl functional group (–C(=O)–). It is thus the simplest amide of carbamic acid.
Urea serves an important r ...
derivatives (R2N)2C=O. A notorious example is the spontaneous reaction of Tetrakis(dimethylamino)ethylene
Tetrakis(dimethylamino)ethylene (TDAE) is an organic compound with the formula (NMe2)2sub>2 (where Me = CH3). A colorless liquid, this compound is classified as an enamine. Primary and secondary enamines tend to isomerize, but tertiary enamines a ...
((H3C)2N)2C=C(N(CH3)2)2 in air with emission of a green-blue light, which was used by downed US Navy
The United States Navy (USN) is the maritime service branch of the United States Armed Forces and one of the eight uniformed services of the United States. It is the largest and most powerful navy in the world, with the estimated tonnage of ...
pilots to signal for help in World War II
World War II or the Second World War, often abbreviated as WWII or WW2, was a world war that lasted from 1939 to 1945. It involved the vast majority of the world's countries—including all of the great powers—forming two opposin ...
.
References
{{reflist Enamines Hypothetical chemical compounds