1,4,7-Trithiacyclononane

1,4,7-Trithiacyclononane (also known as 9-ane-S3) is a heterocyclic compound with the formula (CH2CH2S)3. This organic compound is a colorless liquid that is soluble in organic solvents. It is a cyclic trimer of thioacetaldehyde and a ligand in coordination chemistry.

Structure and Bonding

1,4,7-Trithiacyclononane is a nine-membered ring with alternating carbon and sulfur atoms. It is a cyclic compound and belongs to the class of organosulfur compounds. The molecule is symmetrical, with the three sulfur atoms evenly spaced around the ring. The carbon-sulfur bonds have a length of 1.82 Å, and the carbon-carbon bonds have a length of 1.54 Å.

Synthesis

The synthesis of 1,4,7-trithiacyclononane involves the reaction of thioacetaldehyde with formaldehyde in the presence of a base. The reaction proceeds via a condensation reaction, with the elimination of water.

Applications

1,4,7-Trithiacyclononane is primarily used as a ligand in coordination chemistry. It has a strong affinity for soft metal ions, such as copper, silver, and gold. The resulting complexes have been studied for their potential use in catalysis and nanotechnology.

Safety

Like many organosulfur compounds, 1,4,7-trithiacyclononane has a strong odor and can cause irritation to the eyes and skin. It should be handled with care, using appropriate personal protective equipment.

See Also

• Thioether
• Crown ether
• Coordination chemistry