Zirconium acetylacetonate

Last updated
Zirconium acetylacetonate
Zr(acac)4Clegg.png
Names
Other names
tetrakis(acetylacetonato)zirconium, zirconium tetraacetylacetonate, zirconium tetrakis(acetylacetonate), tetrakis(acetylacetonato) zirconium, Zirconium(IV) 2,4-pentanedionate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.037.721 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 241-510-5
PubChem CID
UNII
  • InChI=1S/4C5H8O2.Zr/c4*1-4(6)3-5(2)7;/h4*3,6H,1-2H3;/b4*4-3-;
    Key: YOBOXHGSEJBUPB-MTOQALJVSA-N
  • CC(=CC(=O)C)O.CC(=CC(=O)C)O.CC(=CC(=O)C)O.CC(=CC(=O)C)O.[Zr]
Properties
C20H28O8Zr
Molar mass 487.660 g·mol−1
Appearancewhite solid
Density 1.419 g/cm3
Melting point 194–195 °C (381–383 °F; 467–468 K)
140 °C in vacuo
Solubility in benzene 200 g/L
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H302, H312, H315, H319, H332, H335
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, 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).

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. [1]

The complex is prepared by treating zirconium oxychloride with acetylacetone: [1]

ZrOCl2 + 4 Hacac → Zr(acac)4 + 2 HCl + H2O

The complex has a square antiprismatic geometry with eight nearly equivalent Zr-O bonds of length 2.19 Å. The molecular symmetry is D2, i.e. the complex is chiral. [2] Compounds of high coordination number tend to be stereochemically nonrigid as indicated by the observation of one methyl signal by proton NMR spectroscopy. [3]

More volatile than Zr(acac)4 is the related complex of 1,1,1-trifluoroacetylacetonate. [3]

Related Research Articles

<span class="mw-page-title-main">Titanium tetrachloride</span> Inorganic chemical compound

Titanium tetrachloride is the inorganic compound with the formula TiCl4. It is an important intermediate in the production of titanium metal and the pigment titanium dioxide. TiCl4 is a volatile liquid. Upon contact with humid air, it forms thick clouds of titanium dioxide and hydrochloric acid, a reaction that was formerly exploited for use in smoke machines. It is sometimes referred to as "tickle" or "tickle 4" due to the phonetic resemblance of its molecular formula to the word.

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

Nickel(II) chloride (or just nickel chloride) is the chemical compound NiCl2. The anhydrous salt is yellow, but the more familiar hydrate NiCl2·6H2O is green. Nickel(II) chloride, in various forms, is the most important source of nickel for chemical synthesis. The nickel chlorides are deliquescent, absorbing moisture from the air to form a solution. Nickel salts have been shown to be carcinogenic to the lungs and nasal passages in cases of long-term inhalation exposure.

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

Hafnium(IV) chloride is the inorganic compound with the formula HfCl4. This colourless solid is the precursor to most hafnium organometallic compounds. It has a variety of highly specialized applications, mainly in materials science and as a catalyst.

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

Zirconium(IV) chloride, also known as zirconium tetrachloride, is an inorganic compound frequently used as a precursor to other compounds of zirconium. This white high-melting solid hydrolyzes rapidly in humid air.

Titanium(III) chloride is the inorganic compound with the formula TiCl3. At least four distinct species have this formula; additionally hydrated derivatives are known. TiCl3 is one of the most common halides of titanium and is an important catalyst for the manufacture of polyolefins.

Zirconium(IV) bromide is the inorganic compound with the formula ZrBr4. This colourless solid is the principal precursor to other Zr–Br compounds.

<span class="mw-page-title-main">Zirconium(IV) iodide</span> Chemical compound

Zirconium(IV) iodide is the chemical compound with the formula ZrI4. It is the most readily available iodide of zirconium. It is an orange-coloured solid that degrades in the presence of water. The compound was once prominent as an intermediate in the purification of zirconium metal.

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

Borohydride refers to the anion [BH4], which is also called tetrahydroborate, and its salts. Borohydride or hydroborate is also the term used for compounds containing [BH4−nXn], where n is an integer from 0 to 3, for example cyanoborohydride or cyanotrihydroborate [BH3(CN)] and triethylborohydride or triethylhydroborate [BH(CH2CH3)3]. Borohydrides find wide use as reducing agents in organic synthesis. The most important borohydrides are lithium borohydride and sodium borohydride, but other salts are well known. Tetrahydroborates are also of academic and industrial interest in inorganic chemistry.

<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">Organozirconium and organohafnium chemistry</span>

Organozirconium chemistry is the science of exploring the properties, structure, and reactivity of organozirconium compounds, which are organometallic compounds containing chemical bonds between carbon and zirconium. Organozirconium compounds have been widely studied, in part because they are useful catalysts in Ziegler-Natta polymerization.

<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.

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">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">1,1,1-Trifluoroacetylacetone</span> Chemical compound

1,1,1-Trifluoroacetylacetone is the organofluorine compound with the formula CF3C(O)CH2C(O)CH3. It is a colorless liquid. Like other 1,3-diketones, it is used as a precursor to heterocycles, e.g. pyrazoles, and metal chelates. It is prepared by condensation of esters of trifluoroacetic acid with acetone.

<span class="mw-page-title-main">Platinum(II) bis(acetylacetonate)</span> Chemical compound

Platinum(II) bis(acetylacetonate) is the coordination compound with the formula Pt(O2C5H7)2, abbreviated Pt(acac)2. The homoleptic acetylacetonate complex of platinum(II), it is a yellow, benzene-soluble solid. According to X-ray crystallography, the Pt center is square planar. The compound is a widely used precursor to platinum-based catalysts.

<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">Holmium acetylacetonate</span> Chemical compound

Holmium acetylacetonate is a coordination complex, with the chemical formula of Ho(C5H7O2)3 or Ho(acac)3. It can be obtained via the reaction between metallic holmium or holmium(III) hydride with acetylacetone, or via the reaction between holmium(III) chloride and ammonium acetylacetonate. Its anhydrous form is stable in a dry atmosphere but forms a hydrate in humid air.

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

Bis(acetylacetonato)iron(II) is a coordination complex of iron with the formula Fe(C5H7O2)2. It can be prepared by reacting iron(II) chloride with 2,4-pentanedione in presence of piperidine.

References

  1. 1 2 Young, R. C.; Arch, Arnold (1946). "Zirconium Acetylacetonate [Tetrakis(2,4‐pentanediono)zirconium]". Inorganic Syntheses. pp. 121–148. doi:10.1002/9780470132333.ch35. ISBN   9780470132333.{{cite book}}: |journal= ignored (help)
  2. Clegg, William (1987). "Redetermination of the structure of tetrakis(acetylacetonato)zirconium(IV)". Acta Crystallographica Section C. 43 (4): 789–91. doi:10.1107/S0108270187094083.
  3. 1 2 Morris, Melvin L.; Moshier, Ross W.; Sievers, Robert E. (1967). "Tetrakis(1,1,1‐trifluoro‐2,4‐pentanedionato)zirconium(and Hafnium)". Tetrakis(1,1,1-trifluoro-2,4-pentanedionato)zirconium (and Hafnium). Inorganic Syntheses. Vol. 9. pp. 50–52. doi:10.1002/9780470132401.ch15. ISBN   9780470131688.