Tetraacetylethane is the
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
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 organic chemistry is the branch of organic chemistry dealing with the synthesis, proper ...
s and
metal complex
A coordination complex is a chemical compound consisting 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 ...
es. It is prepared by oxidation of
sodium acetylacetonate:
: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 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 ...
, tetraacetylethane exists as the
enol
In organic chemistry, enols are a type of functional group or intermediate in organic chemistry containing a group with the formula (R = many substituents). The term ''enol'' is an abbreviation of ''alkenol'', a portmanteau deriving from "-ene ...
, as 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 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