Tetracyanoethylene

Tetracyanoethylene

Names
Preferred IUPAC name Ethenetetracarbonitrile
Other names TCNE
Identifiers
CAS Number	670-54-2 Y
3D model (JSmol)	Interactive image
ChemSpider	12114 Y
ECHA InfoCard	100.010.527
PubChem CID	12635
UNII	C592309ECU Y
CompTox Dashboard (EPA)	DTXSID7049425
InChI InChI=1S/C6N4/c7-1-5(2-8)6(3-9)4-10 Y Key: NLDYACGHTUPAQU-UHFFFAOYSA-N Y InChI=1/C6N4/c7-1-5(2-8)6(3-9)4-10 Key: NLDYACGHTUPAQU-UHFFFAOYAN
SMILES N#CC(C#N)=C(C#N)C#N
Properties
Chemical formula	C6N4
Molar mass	128.094 g·mol−1
Density	1.35 g/cm3
Melting point	199 °C (390 °F; 472 K)
Boiling point	130 to 140 °C (266 to 284 °F; 403 to 413 K) 0.1 mmHg (sublimes)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Tetracyanoethylene (TCNE) is organic compound with the formula C₂(CN)₄. It is a colorless solid. It is an important member of the cyanocarbons.

Chittipeddi refers to TCNE as "tetracyanoethenide".^[2]

Synthesis and reactions[]

TCNE is prepared by brominating malononitrile in the presence of potassium bromide to give the KBr-complex, and dehalogenating with copper.^[1]

Oxidation of TCNE with hydrogen peroxide gives the corresponding epoxide, which has unusual properties.^[3]

Redox chemistry[]

TCNE is often used as an electron acceptor. Cyano groups have low energy π* orbitals, and the presence of four such groups, with their π systems (conjugated) to the central C=C double bond, gives rise to an electrophilic alkene. TCNE is reduced by iodide to give the radical anion:^{[citation needed]}

C₂(CN)₄ + I⁻ → [C₂(CN)₄]⁻ + 1⁄2 I₂

Magnetic properties[]

Because of its planarity and its ability to accept electrons, TCNE has been used to prepare numerous organic superconductors, usually by serving as a single electron oxidant of an organic electron donor. Such charge-transfer salts are sometimes called Bechgaard salts.^{[citation needed]}

Safety[]

TCNE hydrolyzes in moist air to give hydrogen cyanide and should be handled accordingly.^[1]

References[]