|Molecular mass||128.09 g/mol|
|Melting point||199 °C|
|Sublimation||130-140 °C (0.1 mm Hg)|
|Disclaimer and references|
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 linked (conjugated) to the central C=C double bond, gives rise to an excellent acceptor. Thus, treatment of TCNE with iodide salts gives the radical anion:
- C2(CN)4 + I- → [C2(CN)4]- + 0.5 I2
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 salt.
Synthesis and reactions
TCNE is a source of HCN and should be handled accordingly.
- Carboni, R. A. "Tetracyanoethylene" Organic Syntheses, Collected Volume 4, p.877 (1963)
- Linn, W. J. "Tetracyanoethylene Oxide" Organic Syntheses, Collected Volume 5, p.1007 (1973).