Hexafluoroacetylacetone

Hexafluoroacetylacetone (also known as HFAA) is a chemical compound with the formula (CF3CO)2CH2. This fluorocarbon derivative is a colourless, volatile liquid that is highly reactive due to its acidity and ability to act as a ligand.

Structure and Bonding

Hexafluoroacetylacetone is a beta-diketone, which is a class of compounds with two carbonyl groups separated by a single carbon atom. The molecule is planar due to the conjugation of the carbonyl groups and the central methylene group. The fluorine atoms attached to the carbonyl groups contribute to the compound's acidity by stabilizing the negative charge on the oxygen atom in the conjugate base.

Synthesis

Hexafluoroacetylacetone can be synthesized from hexafluoroacetone and formaldehyde in the presence of a base. The reaction proceeds via a Cannizzaro reaction, where one molecule of hexafluoroacetone is reduced to a fluoroalcohol while another is oxidized to hexafluoroacetylacetone.

Applications

Due to its ability to act as a ligand, hexafluoroacetylacetone is used in the preparation of various metal complexes. These complexes have applications in catalysis, material science, and biochemistry.

Safety

Hexafluoroacetylacetone is a highly reactive compound and should be handled with care. It can cause burns and eye damage, and may be harmful if inhaled.