Tetraacetylethane

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Tetraacetylethane
Ac4C2H2.svg
Names
Other names
3,4-diacetyl-2,5-Hexanedione
Identifiers
PubChem CID
Properties
C10H14O4
Molar mass 198.218 g·mol−1
Appearancewhite solid
Density 1.305 g/cm3
Melting point 192–193 °C (378–379 °F; 465–466 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Tetraacetylethane is the organic compound with the nominal formula [CH(C(O)CH3)2]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: [1]

I2 + 2 NaCH(C(O)CH3)2 → [CH(C(O)CH3)2]2 + 2 NaI

Reminiscent of the case of acetylacetone, tetraacetylethane exists as the enol, as established by X-ray crystallography. The two C3O2H rings are twisted with a dihedral angle near 90°. [2]

Many metal complexes have been prepared from the conjugate base of this ligand. One example is diruthenium(III) derivative [Ru(acac)2]2[C(C(O)CH3)2]2, which is closely related to ruthenium(III) acetylacetonate. [3]

Related Research Articles

<span class="mw-page-title-main">Acetylacetone</span> Chemical compound

Acetylacetone is an organic compound with the chemical formula CH3COCH2COCH3. It is a colorless liquid, classified as a 1,3-diketone. It exists in equilibrium with a tautomer CH3C(O)CH=(OH)CH3. These tautomers interconvert so rapidly under most conditions that they are treated as a single compound in most applications. It is a colorless liquid that is a precursor to acetylacetonate anion, a bidentate ligand. It is also a building block for the synthesis of heterocyclic compounds.

<span class="mw-page-title-main">Ruthenium(III) chloride</span> Chemical compound

Ruthenium(III) chloride is the chemical compound with the formula RuCl3. "Ruthenium(III) chloride" more commonly refers to the hydrate RuCl3·xH2O. Both the anhydrous and hydrated species are dark brown or black solids. The hydrate, with a varying proportion of water of crystallization, often approximating to a trihydrate, is a commonly used starting material in ruthenium chemistry.

<span class="mw-page-title-main">Tris(bipyridine)ruthenium(II) chloride</span> Chemical compound

Tris(bipyridine)ruthenium(II) chloride is the chloride salt coordination complex with the formula [Ru(bpy)3]2+ 2Cl. This polypyridine complex is a red crystalline salt obtained as the hexahydrate, although all of the properties of interest are in the cation [Ru(bpy)3]2+, which has received much attention because of its distinctive optical properties. The chlorides can be replaced with other anions, such as PF6.

Ruthenocene is an organoruthenium compound with the formula (C5H5)2Ru. This pale yellow, volatile solid is classified as a sandwich compound and more specifically, as a metallocene.

<span class="mw-page-title-main">Chromium(III) acetylacetonate</span> Chemical compound

Chromium(III) acetylacetonate is the coordination compound with the formula Cr(C5H7O2)3, sometimes designated as Cr(acac)3. This purplish coordination complex is used in NMR spectroscopy as a relaxation agent because of its solubility in nonpolar organic solvents and its paramagnetism.

<span class="mw-page-title-main">Organoruthenium chemistry</span>

Organoruthenium chemistry is the chemistry of organometallic compounds containing a carbon to ruthenium chemical bond. Several organoruthenium catalysts are of commercial interest and organoruthenium compounds have been considered for cancer therapy. The chemistry has some stoichiometric similarities with organoiron chemistry, as iron is directly above ruthenium in group 8 of the periodic table. The most important reagents for the introduction of ruthenium are ruthenium(III) chloride and triruthenium dodecacarbonyl.

<span class="mw-page-title-main">Nickel(II) bis(acetylacetonate)</span> Coordination complex

Nickel(II) bis(acetylacetonate) is a coordination complex with the formula [Ni(acac)2]3, where acac is the anion C5H7O2 derived from deprotonation of acetylacetone. It is a dark green paramagnetic solid that is soluble in organic solvents such as toluene. It reacts with water to give the blue-green diaquo complex Ni(acac)2(H2O)2.

<span class="mw-page-title-main">Ruthenium(III) acetylacetonate</span> Chemical compound

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 to other compounds of ruthenium.

<span class="mw-page-title-main">Tris(acetylacetonato)iron(III)</span> Chemical compound

Tris(acetylacetonato) iron(III), often abbreviated Fe(acac)3, is a ferric coordination complex featuring acetylacetonate (acac) ligands, making it one of a family of metal acetylacetonates. It is a red air-stable solid that dissolves in nonpolar organic solvents.

Metal acetylacetonates are coordination complexes derived from the acetylacetonate anion (CH
3
COCHCOCH
3
) and metal ions, usually transition metals. The bidentate ligand acetylacetonate is often abbreviated acac. Typically both oxygen atoms bind to the metal to form a six-membered chelate ring. The simplest complexes have the formula M(acac)3 and M(acac)2. Mixed-ligand complexes, e.g. VO(acac)2, are also numerous. Variations of acetylacetonate have also been developed with myriad substituents in place of methyl (RCOCHCOR). Many such complexes are soluble in organic solvents, in contrast to the related metal halides. Because of these properties, acac complexes are sometimes used as catalyst precursors and reagents. Applications include their use as NMR "shift reagents" and as catalysts for organic synthesis, and precursors to industrial hydroformylation catalysts. C
5
H
7
O
2
in some cases also binds to metals through the central carbon atom; this bonding mode is more common for the third-row transition metals such as platinum(II) and iridium(III).

<span class="mw-page-title-main">Vanadyl acetylacetonate</span> Chemical compound

Vanadyl acetylacetonate is the chemical compound with the formula VO(acac)2, where acac is the conjugate base of acetylacetone. It is a blue-green solid that dissolves in polar organic solvents. The coordination complex consists of the vanadyl group, VO2+, bound to two acac ligands via the two oxygen atoms on each. Like other charge-neutral acetylacetonate complexes, it is not soluble in water.

<span class="mw-page-title-main">Half sandwich compound</span> Class of coordination compounds

Half sandwich compounds, also known as piano stool complexes, are organometallic complexes that feature a cyclic polyhapto ligand bound to an MLn center, where L is a unidentate ligand. Thousands of such complexes are known. Well-known examples include cyclobutadieneiron tricarbonyl and (C5H5)TiCl3. Commercially useful examples include (C5H5)Co(CO)2, which is used in the synthesis of substituted pyridines, and methylcyclopentadienyl manganese tricarbonyl, an antiknock agent in petrol.

<span class="mw-page-title-main">Iridium acetylacetonate</span> Chemical compound

Iridium acetylacetonate is the iridium coordination complex with the formula Ir(O2C5H7)3, which is sometimes known as Ir(acac)3. The molecule has D3-symmetry. It is a yellow-orange solid that is soluble in organic solvents.

<span class="mw-page-title-main">Pentamethylcyclopentadienyl ruthenium dichloride dimer</span> Chemical compound

Pentamethylcyclopentadienyl ruthenium dichloride is an organoruthenium chemistry with the formula [(C5(CH3)5)RuCl2]2, commonly abbreviated [Cp*RuCl2]2. This brown paramagnetic solid is a reagent in organometallic chemistry. It is an unusual example of a compound that exists as isomers that differ in the intermetallic separation, a difference that is manifested in a number of physical properties.

<span class="mw-page-title-main">Rhodium acetylacetonate</span> Chemical compound

Rhodium acetylacetonate is the coordination complex with the formula Rh(O2C5H7)3, which is sometimes known as Rh(acac)3. The molecule has D3-symmetry. It is a yellow-orange solid that is soluble in organic solvents.

<span class="mw-page-title-main">Vanadium(III) acetylacetonate</span> Chemical compound

Vanadium(III) acetylacetonate is the coordination compound with the formula V(C5H7O2)3, sometimes designated as V(acac)3. It is an orange-brown solid that is soluble in organic solvents.

A transition metal phosphido complex is a coordination complex containing a phosphido ligand (R2P, where R = H, organic substituent). With two lone pairs on phosphorus, the phosphido anion (R2P) is comparable to an amido anion (R2N), except that the M-P distances are longer and the phosphorus atom is more sterically accessible. For these reasons, phosphido is often a bridging ligand. The -PH2 ion or ligand is also called phosphanide or phosphido ligand.

<span class="mw-page-title-main">Tris(acetylacetonato)cobalt(III)</span> Chemical compound

Tris(acetylacetonato)cobalt(III) is the coordination complex with the formula Co(C5H7O2)3. Often abbreviated Co(acac)3, it is a green, diamagnetic solid that is soluble in organic solvents, but not in water. Owing to its solubility in organic solvents, tris(acetylacetonato)cobalt(III) is used to produce homogeneous catalysts by reduction.

<span class="mw-page-title-main">Tris(acetylacetonato)titanium(III)</span> Chemical compound

Tris(acetylacetonato)titanium(III), often abbreviated Ti(acac)3, is a coordination complex of titanium(III) featuring acetylacetonate (acac) ligands, making it one of a family of metal acetylacetonates. It is a blue air-sensitive solid that dissolves in nonpolar organic solvents. The compound is prepared by treating titanium trichloride with acetylacetone in the presence of base. Being paramagnetic, it gives a contact-shifted proton NMR signal at 60 ppm upfield of TMS assigned to the methyl group.

<span class="mw-page-title-main">Sodium acetylacetonate</span> Chemical compound

Sodium acetylacetonate is an organic compound with the nominal formula Na[CH(C(O)CH3)2]. This white, water-soluble solid is the conjugate base of acetylacetone.

References

  1. Robert G. Charles (1959). "Tetraacetylethane". Organic Syntheses. 39: 61. doi:10.15227/orgsyn.039.0061.
  2. Paula M. B. Piccoli, Thomas F. Koetzle, Arthur J. Schultz, Elizabeth A. Zhurova, Jernej Stare, A. Alan Pinkerton, Juergen Eckert, and Dusan Hadzi (2008). "Variable Temperature Neutron Diffraction and X-Ray Charge Density Studies of Tetraacetylethane". J. Phys. Chem. A. 112 (29): 6667–6677. Bibcode:2008JPCA..112.6667P. doi:10.1021/jp800204r. PMID   18593102.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. Koiwa, Tomohiro; Masuda, Yuki; Shono, Junpei; Kawamoto, Yuji; Hoshino, Yoshimasa; Hashimoto, Takeshi; Natarajan, Karuppannan; Shimizu, Kunio (2004). "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)". Inorganic Chemistry. 43 (20): 6215–6223. doi:10.1021/ic030216c. PMID   15446866.