The key difference between acetylacetone and acetylacetonate ion is that acetylacetone is an organic compound that belongs to the 1,3-diketone category, whereas acetylacetonate ion is the anion derived from acetylacetonate organic compound.
Acetylacetone is an organic compound having the chemical formula CH3COCH2COCH3. Acetylacetonate ion is a negatively charged chemical species derived from acetylacetone. We can categorize these two chemical species according to their formal charges; acetylacetonate has a zero formal charge while acetylacetonate ion has a -1 negative charge.
CONTENTS
1. Overview and Key Difference
2. What is Acetylacetone
3. What is Acetylacetonate Ion
4. Acetylacetone vs Acetylacetonate Ion in Tabular Form
5. Summary – Acetylacetone vs Acetylacetonate Ion
What is Acetylacetone?
Acetylacetone is an organic compound having the chemical formula CH3COCH2COCH3. It occurs as a colorless liquid, and we can classify this compound as a 1,3-diketone. Typically, this compound exists in equilibrium with the tautomer form. Moreover, acetylacetone is the precursor for acetylacetonate anion, which is a bidentate ligand. In addition, it serves as the building block for the synthesis of heterocyclic compounds. Acetylacetone is a weak acid.
Figure 01: The Chemical Structure of Acetyacetone
Furthermore, keto and enol tautomers of acetylacetone tend to coexist in solution. In the enol form, the hydrogen atom is shared equally between the two oxygen atoms. We can distinguish the two tautomeric forms by NMR spectroscopy, IR spectroscopy, and other methods.
Furthermore, the equilibrium constant is high in nonpolar solvents, where the keto form becomes more favorable in polar, hydrogen-bonding solvents, including water. In contrast, the enol form is the vinylogous analogue of a carboxylic acid.
We can prepare this compound industrially through the thermal rearrangement of isopropenyl acetate. However, in laboratories, we can begin this preparation with acetone and acetic anhydride in the presence of boron trifluoride catalyst.
What is Acetylacetonate Ion?
Acetylacetonate ion is a negatively charged chemical species derived from acetylacetone. The formal charge on this anion is -1. This anion can act as a bidentate ligand for complex formation in coordination chemistry. There are two oxygen atoms in this anion having lone electron pairs that can be donated to a suitable metal cation center. Therefore, acetylacetonate anion is important in coordination chemistry as a ligand.
Since acetylacetone is a weak acid, it tends to exist in equilibrium with its conjugate base and release proton when it is in an aqueous solution. The conjugate base of this acid is acetylacetonate anion. This anion is attracted by the metal cations because of the opposite charge attraction forces.
What is the Difference Between Acetylacetone and Acetylacetonate Ion?
Acetylacetone is an organic compound having the chemical formula CH3COCH2COCH3, while Acetylacetonate ion is a negatively charged chemical species derived from acetylacetone. Therefore, the key difference between acetylacetone and acetylacetonate ion is that acetylacetone is an organic compound that belongs to the 1,3-diketone category, whereas acetylacetonate ion is the anion derived from acetylacetonate organic compound. Acetylacetone compound has a zero formal charge, while the acetylacetonate ion has a formal charge of -1.
Below is a summary of the difference between acetylacetone and acetylacetonate ion in tabular form for side by side comparison.
Summary – Acetylacetone vs Acetylacetonate Ion
Acetylacetone and acetylacetonate ions are related chemical species because the acetylacetonate ion is formed from the removal of protons from acetylacetone compounds. The key difference between acetylacetone and acetylacetonate ion is that acetylacetone is an organic compound that belongs to the 1,3-diketone category, whereas acetylacetonate ion is the anion derived from acetylacetonate organic compound.
Reference:
1. “Acetylacetonate.” An Overview | ScienceDirect Topics.
2. “Acetylacetonate.” Structures with Bidentate Ligands.
3. “Acetylacetone.” National Center for Biotechnology Information. PubChem Compound Database, U.S. National Library of Medicine.
Image Courtesy:
1. “Acetyloaceton” By Arrowsmaster – Own work (Public Domain) via Commons Wikimedia
2. “CNX Chem 19 02 Colors” By OpenStax – (CC BY 4.0) via Commons Wikimedia