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. T ...
with the nominal formula
H(C(O)CH3)2sub>2. It is a white solid that has attracted interest as a precursor to
heterocycle
A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and ...
s 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. Many ...
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 + CH ...
:
:I
2 + 2 NaCH(C(O)CH
3)
2 →
H(C(O)CH3)2sub>2 + 2 NaI
Reminiscent of the case of
acetylacetone, tetraacetylethane exists as the
enol
In organic chemistry, alkenols (shortened to enols) are a type of reactive structure or intermediate in organic chemistry that is represented as an alkene ( olefin) with a hydroxyl group attached to one end of the alkene double bond (). The t ...
, 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 angles ...
. 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.
[{{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