Rhodium acetylacetonate

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Rhodium acetylacetonate
Rh(acac)3.png
Names
IUPAC name
(E)-4-hydroxypent-3-en-2-one;rhodium
Other names
Rhodium(III) acetylacetonate
Identifiers
3D model (JSmol)
ECHA InfoCard 100.034.704 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 238-192-5
PubChem CID
  • InChI=1S/3C5H8O2.Rh/c3*1-4(6)3-5(2)7;/h3*3,6H,1-2H3;/b3*4-3+;
    Key: MBVAQOHBPXKYMF-MUCWUPSWSA-N
  • coordination form:CC(=C[C-](C)O1)O[Rh+3]123(OC(=C[C-](C)O2)C)OC(=C[C-](C)O3)C
  • ionic form:CC(=O)C=C(C)[O-].CC(=O)C=C(C)[O-].CC(=O)C=C(C)[O-].[Rh+3]
Properties
C15H21O6Rh
Molar mass 400.232 g·mol−1
Appearanceorange solid
Melting point 260 °C (500 °F; 533 K) (decomposes)
Hazards
GHS labelling:
GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
Warning
H302, H312, H315, H319, H332, H335, H361
P201, P202, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P308+P313, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Rhodium acetylacetonate is the coordination complex with the formula Rh(C5H7O2)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.

It is prepared from RhCl3(H2O)3 and acetylacetone. [1] The complex has been resolved into individual enantiomers by separation of its adduct with dibenzoyltartaric acid. [2]

Related Research Articles

<span class="mw-page-title-main">Wilkinson's catalyst</span> Chemical compound

Wilkinson's catalyst (chlorido­tris(triphenylphosphene)­rhodium(I)) is a coordination complex of rhodium with the formula [RhCl(PPh3)3], where 'Ph' denotes a phenyl group. It is a red-brown colored solid that is soluble in hydrocarbon solvents such as benzene, and more so in tetrahydrofuran or chlorinated solvents such as dichloromethane. The compound is widely used as a catalyst for hydrogenation of alkenes. It is named after chemist and Nobel laureate Sir Geoffrey Wilkinson, who first popularized its use.

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

Rhodium(III) chloride refers to inorganic compounds with the formula RhCl3(H2O)n, where n varies from 0 to 3. These are diamagnetic solids featuring octahedral Rh(III) centres. Depending on the value of n, the material is either a dense brown solid or a soluble reddish salt. The soluble trihydrated (n = 3) salt is widely used to prepare compounds used in homogeneous catalysis, notably for the industrial production of acetic acid and hydroformylation.

Cycloocta-1,5-diene is a cyclic hydrocarbon with the chemical formula C8H12, specifically [−(CH2)2−CH=CH−]2.

<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">Organorhodium chemistry</span> Field of study

Organorhodium chemistry is the chemistry of organometallic compounds containing a rhodium-carbon chemical bond, and the study of rhodium and rhodium compounds as catalysts in organic reactions.

<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.

<span class="mw-page-title-main">Rhodocene</span> Organometallic chemical compound

Rhodocene is a chemical compound with the formula [Rh(C5H5)2]. Each molecule contains an atom of rhodium bound between two planar aromatic systems of five carbon atoms known as cyclopentadienyl rings in a sandwich arrangement. It is an organometallic compound as it has (haptic) covalent rhodium–carbon bonds. The [Rh(C5H5)2] radical is found above 150 °C (302 °F) or when trapped by cooling to liquid nitrogen temperatures (−196 °C [−321 °F]). At room temperature, pairs of these radicals join via their cyclopentadienyl rings to form a dimer, a yellow solid.

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">Tris(triphenylphosphine)rhodium carbonyl hydride</span> Chemical compound

Carbonyl hydrido tris(triphenylphosphine)rhodium(I) [Carbonyl(hydrido)tris(triphenylphosphane)rhodium(I)] is an organorhodium compound with the formula [RhH(CO)(PPh3)3] (Ph = C6H5). It is a yellow, benzene-soluble solid, which is used industrially for hydroformylation.

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

Aluminium acetylacetonate, also referred to as Al(acac)3, is a coordination complex with formula Al(C5H7O2)3. This aluminium complex with three acetylacetone ligands is used in research on Al-containing materials. The molecule has D3 symmetry, being isomorphous with other octahedral tris(acetylacetonate)s.

Barium acetylacetonate is a compound with formula Ba(C5H7O2)2. It is the Ba2+ complex of the anion acetylacetonate. The compound is typically encountered as an ill-defined hydrate, which would accord with the high coordination number characteristic of barium.

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

Europium acetylacetonate is a coordination complex with formula Eu(C5H7O2)3. Although this anhydrous acetylacetonate complex is widely discussed, some sources suggest that it is really the dihydrate Eu(C5H7O2)3(H2O)2.

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

Gadolinium acetylacetonate is a coordination compound with the formula Gd(C5H7O2)3. This anhydrous acetylacetonate complex is widely discussed but unlikely to exist per se. The 8-coordinated dihydrate Gd(C5H7O2)3(H2O)2 is a more plausible formula based on the behavior of other lathanide complexes. It has also been characterized twice by X-ray crystallography.

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

Gallium acetylacetonate, also referred to as Ga(acac)3, is a coordination complex with formula Ga(C5H7O2)3. This gallium complex with three acetylacetonate ligands is used in research. The molecule has D3 symmetry, being isomorphous with other octahedral tris(acetylacetonate)s.

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

Hafnium acetylacetonate, also known as Hf(acac)4, is a coordination compound with formula Hf(C5H7O2)4. This white solid is the main hafnium complex of acetylacetonate. The complex has a square antiprismatic geometry with eight nearly equivalent Hf-O bonds. The molecular symmetry is D2, i.e., the complex is chiral. It is prepared from hafnium tetrachloride and acetylacetone, and base. Zr(acac)4 is very similar in structure and properties.

<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">Dicarbonyl(acetylacetonato)rhodium(I)</span> Chemical compound

Dicarbonyl(acetylacetonato)rhodium(I) is an organorhodium compound with the formula Rh(O2C5H7)(CO)2. The compound consists of two CO ligands and an acetylacetonate. It is a dark green solid that dissolves in acetone and benzene, giving yellow solutions. The compound is used as a precursor to homogeneous catalysts.

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

Zirconium acetylacetonate is the coordination complex with the formula Zr(C5H7O2)4. It is a common acetylacetonate of zirconium. It is a white solid that exhibits high solubility in nonpolar organic solvents, but not simple hydrocarbons.

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

Neodymium(III) acetylacetonate is a coordination compound with the chemical formula Nd(O2C5H7)3. Although many sources discuss this anhydrous acetylacetonate complex, it is the dihydrate Nd(O2C5H7)3(H2O)2 that has been characterized by X-ray crystallography. It commonly occurs as a white powder. Upon heating under vacuum, other dihydrated lanthanide trisacetylacetonates convert to oxo-clusters M4O(C5H7O2)10. This result suggests that Nd(O2C5H7)3 may not exist.

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

Holmium acetylacetonate is a coordination compound with the formula Ho(C5H7O2)3. This anhydrous acetylacetonate complex is often discussed but unlikely to exist per se. The 8-coordinated dihydrate Ho(C5H7O2)3(H2O)2 is a more plausible formula based on the behavior of other lanthanide acetylacetonates. The dihydrate has been characterized by X-ray crystallography.

References

  1. James E. Collins, Michael P. Castellani, Arnold L. Rheingold, Edward J. Miller, William E. Geiger, Anne L. Rieger, Philip H. Rieger "Synthesis, Characterization, and Molecular Structure of Bis(tetraphenylcyclopentdienyl)rhodium(II)" Organometallics 1995, pp 1232–1238. doi : 10.1021/om00003a025
  2. Drake, A. F.; Gould, J. M.; Mason, S. F.; Rosini, C.; Woodley, F. J. (1983). "The optical resolution of tris(pentane-2,4-dionato)metal(III) complexes". Polyhedron. 2 (6): 537–538. doi:10.1016/S0277-5387(00)87108-9.