Tetraacetylethane is the
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon- hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. Th ...
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 complex
A coordination complex consists of a central atom or ion, which is usually metallic and is called the ''coordination centre'', and a surrounding array of bound molecules or ions, that are in turn known as '' ligands'' or complexing agents. Man ...
es. It is prepared by oxidation of
sodium acetylacetonate
Sodium acetylacetonate is an organic compound with the nominal formula Na H(C(O)CH3)2 This white, water-soluble solid is the conjugate base of acetylacetone.
Preparation
The compound is prepared by deprotonation of acetylacetone:
:NaOH + CH2( ...
:
:I
2 + 2 NaCH(C(O)CH
3)
2 →
H(C(O)CH3)2sub>2 + 2 NaI
Reminiscent of the case of
acetylacetone
Acetylacetone is an organic compound with the chemical formula . It is a colorless liquid, classified as a 1,3- diketone. It exists in equilibrium with a tautomer . These tautomers interconvert so rapidly under most conditions that they are tr ...
, tetraacetylethane exists as the
enol, as established by
X-ray crystallography
X-ray crystallography is the experimental science determining the atomic and molecular structure of a crystal, in which the crystalline structure causes a beam of incident X-rays to diffract into many specific directions. By measuring the angle ...
. The two C
3O
2H rings are twisted with a dihedral angle near 90°.
Many metal complexes have been prepared from the conjugate base of this ligand. One example is diruthenium(III) derivative
u(acac)2sub>2
(C(O)CH3)2sub>2, which is closely related to
ruthenium(III) acetylacetonate
Ruthenium(III) acetylacetonate is a coordination complex with the formula Ru(O2C5H7)3. O2C5H7− is the ligand called acetylacetonate. This compound exists as a dark violet solid that is soluble in most organic solvents. It is used as a precursor ...
.
[{{cite journal , doi=10.1021/ic030216c, title=Synthesis, Characterization, and Detailed Electrochemistry of Binuclear Ruthenium(III) Complexes Bridged by Bisacetylacetonate. Crystal and Molecular Structures of Ru(acac)2}2(tae)(Acac = 2,4-Pentanedionate Ion, tae = 1,1,2,2-Tetraacetylethanate Dianion), year=2004, last1=Koiwa, first1=Tomohiro, last2=Masuda, first2=Yuki, last3=Shono, first3=Junpei, last4=Kawamoto, first4=Yuji, last5=Hoshino, first5=Yoshimasa, last6=Hashimoto, first6=Takeshi, last7=Natarajan, first7=Karuppannan, last8=Shimizu, first8=Kunio, journal=Inorganic Chemistry, volume=43, issue=20, pages=6215–6223, pmid=15446866]
References
Diketones
Chelating agents
Ligands
3-Hydroxypropenals