Acetylacetone
Acetylacetone
Acetylacetone is an organic compound with the formula C5H8O2. It is a colorless liquid that is a precursor to acetylacetonate, a common bidentate ligand. Acetylacetone exists in two tautomeric forms that rapidly interconvert.
Structure and Properties[edit | edit source]
Acetylacetone is notable for its keto-enol tautomerism, where the keto form (pentane-2,4-dione) and the enol form (4-hydroxy-3-penten-2-one) are in equilibrium. The enol form is stabilized by intramolecular hydrogen bonding.
The equilibrium between the keto and enol forms is influenced by the solvent and temperature. In non-polar solvents, the enol form is predominant, while in polar solvents, the keto form is more stable.
Synthesis[edit | edit source]
Acetylacetone can be synthesized by the thermal rearrangement of isopropenyl acetate or by the reaction of acetone with acetic anhydride in the presence of a base. The synthesis involves the formation of a diketone structure.
Reactions[edit | edit source]
Acetylacetone is a versatile ligand in coordination chemistry. It forms stable complexes with many metal ions, such as vanadium, copper, and iron. The resulting metal acetylacetonates are often used as catalysts or precursors to other chemical compounds.
Applications[edit | edit source]
Acetylacetone is used in the preparation of metal acetylacetonates, which are important in various industrial processes. It is also used as a solvent and as a chemical intermediate in organic synthesis.
Related Compounds[edit | edit source]
The acetylacetonate anion, derived from acetylacetone, is a common ligand in coordination chemistry. It forms chelate complexes with many transition metals.
Gallery[edit | edit source]
Vanadyl acetylacetonate
Related Pages[edit | edit source]
Acetylacetone structure
Keto-enol tautomerism of acetylacetone
Tautomeric forms of acetylacetone
Acetylacetonate anion
Synthesis of acetylacetone
Vanadyl acetylacetonate structure
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