Tetracyanoethylene

• TCNE
• Ethentetracarbonitril
• Percyanoethen

Pure: colorless, commercially available: beige to yellowish mass

Fixed

1.35 g · cm -3

201-202 ° C

223 ° C

• Hydrolyzed in water
• Soluble in dichloromethane

Risk

5 mg · kg -1 ( LD50, rat, oral)

Template: Infobox chemical / molecular formula search available

Tetracyanoethylene - also abbreviated TCNE ( tetracyanoethylene ) - is a hygroscopic organic compound from the substance group of nitriles and has a flat, planar structure.

Preparation and Reactions

Tetracyanoethylene is prepared by bromination of malononitrile in the presence of potassium bromide, potassium bromide, wherein a complex is obtained which is then dehalogenated with copper powder in the heat.

Oxidation of tetracyanoethylene with hydrogen peroxide leads to the corresponding epoxide having an epoxide for unusual chemical properties.

Properties

Tetracyanoethylene sublimed at 130-140 ° C and 0.133 hPa

TCNE is often used as the electron acceptor. Cyano point * orbitals on low energy, and the presence of four such groups, the systems connected via the central C = C double bond ( conjugated) are obtained an excellent electron acceptor. So TCNE reacts with iodide to form the radical anion.

Use

Because of the planarity of the molecule and its ability to readily accept electrons, TCNE has also been used to produce a number of organic superconductors - commonly referred to as an electron - oxidant is an organic Elektrondonator. Such a charge-transfer complexes are sometimes called Bechgaard salts.

Security

TCNE hydrolyzed in water and moist air to highly toxic hydrogen cyanide. Appropriate precautions should be observed when handling the substance.