Sodium acetylacetonate is an
organic compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
with the nominal formula Na
H(C(O)CH3)2 This white, water-soluble solid is the conjugate base of
acetylacetone
Acetylacetone is an organic compound with the chemical formula . It is classified as a 1,3-diketone. It exists in equilibrium with a tautomer . The mixture is a colorless liquid. These tautomers interconvert so rapidly under most conditions that ...
.
[
]
Preparation
The compound is prepared by deprotonation of acetylacetone:
sodium hydride
Sodium hydride is the chemical compound with the empirical formula Na H. This alkali metal hydride is primarily used as a strong yet combustible base in organic synthesis. NaH is a saline (salt-like) hydride, composed of Na+ and H− ions, in co ...
in an aprotic solvent such as THF:
Reactions
Oxidation of the salt gives tetraacetylethane
Tetraacetylethane is the organic compound with the nominal formula H(C(O)CH3)2sub>2. It is a white solid that has attracted interest as a precursor to heterocycles and metal complexes. It is prepared by oxidation of sodium acetylacetonate:
:I2 + ...
.[
With metal salts, it reacts to give metal acetylacetonate complexes.
Alkylation of sodium acetylacetonate can result in both O-alkylation and C-alkylation. The former gives the enol ether and the latter gives 3-substituted derivative of acetylacetone.
]
Structure
The structure of the monohydrate has been established by X-ray crystallography
X-ray crystallography is the experimental science of determining the atomic and molecular structure of a crystal, in which the crystalline structure causes a beam of incident X-rays to Diffraction, diffract in specific directions. By measuring th ...
. The sodium cation is bonded to the enolate oxygen centers.
References
{{Acetylacetonate complexes
Diketones
Chelating agents
Ligands
Acetylacetonate complexes
3-Hydroxypropenals