Misplaced Pages

Tetraaminoethylene

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Hypothetical organic molecule ((H2N)2C=C(NH2)2)
Tetraaminoethylene
Names
Systematic IUPAC name Ethene-1,1,2,2-tetramine
Other names Ethylenetetraamine
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C2H8N4/c3-1(4)2(5)6/h3-6H2Key: XXWSZMQKQLNDLC-UHFFFAOYSA-N
SMILES
  • NC(N)=C(N)N
Properties
Chemical formula C2H8N4
Molar mass 88.114 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

In organic chemistry, tetraaminoethylene is a hypothetical, organic compound with formula C2N4H8 or (H2N)2C=C(NH2)2. Like all polyamines that are geminal, 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.

General chemical structure of tetraaminoethylene derivatives

Tetraaminoethylenes are important in organic chemistry as dimers of diaminocarbenes, a type of stable carbene with the general formula (R2N)2C:.

Reactions

  • Tetraaminoethylenes react with acids to give formamidinium salts.
  • Tetraaminoethylenes react with oxygen to give urea derivatives (R2N)2C=O. A notorious example is the spontaneous reaction of Tetrakis(dimethylamino)ethylene ((H3C)2N)2C=C(N(CH3)2)2 in air with emission of a green-blue light, which was used by downed US Navy pilots to signal for help in World War II.

References

  1. "CID 17899866 - PubChem Public Chemical Database". The PubChem Project. USA: National Center for Biotechnology Information.
  2. Stephen A. Lawrence (2004), Amines: synthesis, properties and applications. Cambridge University Press. ISBN 0-521-78284-8, 371 pages.
Categories: