3D model (JSmol)
|Molar mass||128.09 g·mol−1|
|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)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Synthesis and reactions
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]− + 1⁄2 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 salts.