Tetracyanoethylene

Tetracyanoethylene (TCNE) is a chemical compound with the formula C₂(CN)₄. This organic compound is a colourless solid that is soluble in organic solvents. It is a prominent and widely studied reagent in coordination chemistry and organic chemistry.

Structure and Bonding

Tetracyanoethylene is a planar molecule. The C-C bond length is 1.34 Å, which is shorter than a typical C-C single bond (1.54 Å) but longer than a typical C=C double bond (1.34 Å). This bond length is consistent with a C-C bond order of approximately 1.5. The C-N bond length is 1.16 Å, which is typical for a C≡N triple bond.

Synthesis

Tetracyanoethylene can be synthesized from malononitrile in the presence of a base such as sodium hydroxide.

Applications

Tetracyanoethylene is used as a reagent in organic chemistry for the synthesis of various organic compounds. It is also used in coordination chemistry as a ligand.

Safety

Tetracyanoethylene is a highly reactive compound and should be handled with care. It can cause skin and eye irritation, and prolonged exposure can lead to serious health problems.

See also

• Malononitrile
• Coordination chemistry
• Organic chemistry