Zinc acetylacetonate

Last updated
Zinc acetylacetonate
Zink(II)-acetylacetonat.svg
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.034.405 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 237-860-3
  • 一hydrate:683-082-6
PubChem CID
UNII
  • InChI=1S/2C5H8O2.Zn/c2*1-4(6)3-5(2)7;/h2*3,6H,1-2H3;/q;;+2/p-2/b2*4-3-;
    Key: CYDXJXDAFPJUQE-FDGPNNRMSA-L
  • 一hydrate:InChI=1S/2C5H8O2.H2O.Zn/c2*1-4(6)3-5(2)7;;/h2*3,6H,1-2H3;1H2;/q;;;+2/p-2/b2*4-3-;;
    Key: KUJHAYOLESEVSA-SUKNRPLKSA-L
  • C/C(=C/C(=O)C)/[O-].C/C(=C/C(=O)C)/[O-].[Zn+2]
  • 一hydrate:C/C(=C/C(=O)C)/[O-].C/C(=C/C(=O)C)/[O-].O.[Zn+2]
Properties
C10H14O4Zn
Molar mass 263.60 g·mol−1
Appearancecrystals [1]
Density 1.41 g·cm−3 [2]
Melting point 124–126 °C [1]
Boiling point 129–131 °C (13 hPa) [1]
6.9 g/L [1]
Solubility soluble in organic solvants [3]
Hazards
GHS labelling: [4]
GHS-pictogram-exclam.svg
Warning
H315, H319, H335
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Related compounds
Other cations
calcium acetylacetonate
barium acetylacetonate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Zinc acetylacetonate is an acetylacetonate complex of zinc, with the chemical formula of Zn(C5H7O2)2. The compound is in fact a trimer, Zn3(acac)6, in which each Zn ion is coordinated by five oxygen atoms in a distorted trigonal bipyramidal structure. [5]

Contents

Preparation

Zinc acetylacetonate can be obtained by reacting zinc sulfate, acetylacetone and sodium hydroxide. [3]

Properties

Zinc acetylacetonate is a crystalline substance that is slightly soluble in water. [1] Through sublimation, monomer crystals can be obtained, which are monoclinic and have the space group C2/c (No. 15). [6] Trimeric crystals can also be obtained by sublimation, which is also monoclinic, with space group C2 (No. 5). [2] The structures of its monohydrate [7] and dihydrate [8] are also known.

Reactions

Zinc acetylacetonate hydrate has been used to prepare magnetic (Zn,Fe)Fe2O4 films, [9] zinc oxide, [10] and is also a catalyst for organic synthesis. [3]

Related Research Articles

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

Zinc chloride is the name of inorganic chemical compounds with the formula ZnCl2. It forms hydrates. Zinc chloride, anhydrous and its hydrates are colorless or white crystalline solids, and are highly soluble in water. Five hydrates of zinc chloride are known, as well as four forms of anhydrous zinc chloride. This salt is hygroscopic and even deliquescent. Zinc chloride finds wide application in textile processing, metallurgical fluxes, and chemical synthesis. No mineral with this chemical composition is known aside from the very rare mineral simonkolleite, Zn5(OH)8Cl2·H2O.

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

Zinc acetate is a salt with the formula Zn(CH3CO2)2, which commonly occurs as the dihydrate Zn(CH3CO2)2·2H2O. Both the hydrate and the anhydrous forms are colorless solids that are used as dietary supplements. When used as a food additive, it has the E number E650.

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

Palladium(II) acetate is a chemical compound of palladium described by the formula [Pd(O2CCH3)2]n, abbreviated [Pd(OAc)2]n. It is more reactive than the analogous platinum compound. Depending on the value of n, the compound is soluble in many organic solvents and is commonly used as a catalyst for organic reactions.

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

Erbium(III) chloride is a violet solid with the formula ErCl3. It is used in the preparation of erbium metal.

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

Iron(II) fluoride or ferrous fluoride is an inorganic compound with the molecular formula FeF2. It forms a tetrahydrate FeF2·4H2O that is often referred to by the same names. The anhydrous and hydrated forms are white crystalline solids.

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

Chromium(II) chloride describes inorganic compounds with the formula CrCl2(H2O)n. The anhydrous solid is white when pure, however commercial samples are often grey or green; it is hygroscopic and readily dissolves in water to give bright blue air-sensitive solutions of the tetrahydrate Cr(H2O)4Cl2. Chromium(II) chloride has no commercial uses but is used on a laboratory-scale for the synthesis of other chromium complexes.

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

Palladium(II) bis(acetylacetonate) is a compound with formula Pd(C5H7O2)2. This yellow solid is the most common palladium complex of acetylacetonate. This compound is commercially available and used as a catalyst precursor in organic synthesis. The molecule is relatively planar with idealized D2h symmetry.

<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">Cobalt(II) carbonate</span> Chemical compound

Cobalt(II) carbonate is the inorganic compound with the formula CoCO3. This reddish paramagnetic solid is an intermediate in the hydrometallurgical purification of cobalt from its ores. It is an inorganic pigment, and a precursor to catalysts. Cobalt(II) carbonate also occurs as the rare red/pink mineral spherocobaltite.

Zinc compounds are chemical compounds containing the element zinc which is a member of the group 12 of the periodic table. The oxidation state of zinc in most compounds is the group oxidation state of +2. Zinc may be classified as a post-transition main group element with zinc(II). Zinc compounds are noteworthy for their nondescript behavior, they are generally colorless, do not readily engage in redox reactions, and generally adopt symmetrical structures.

<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">Metaboric acid</span> Chemical compound

Metaboric acid is the name for a family of inorganic compounds with the same empirical formula HBO2. that differ in their molecular structure. They are colourless water-soluble solids formed by the dehydration or decomposition of boric acid.

<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.

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

Dysprosium acetylacetonate is a chemical compound of dysprosium with formula Dy(C5H7O2)3(H2O)n.

<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">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">Praseodymium acetylacetonate</span> Chemical compound

Praseodymium acetylacetonate is a coordination compound with the chemical formula Pr(C5H7O2)3, or Pr(acac)3 for short. Its instability constants (logYn) are 2.89, 4.17 and 5.29 (corresponding to n=1, 2, 3). It can be prepared by the reaction of trialkoxypraseodymium and acetylacetone. When praseodymium chloride reacts with sodium acetylacetonate or lithium acetylacetonate in the solid phase, praseodymium acetylacetonate can also be obtained, but NaPr(acac)4 or LiPr(acac)4 will also be generated. It can form the green complex Pr(acac)3(phen) with o-phenanthroline.

References

  1. 1 2 3 4 5 Sigma-Aldrich Co., product no. 8.08803.
  2. 1 2 Bennett, M. J.; Cotton, F. A.; Eiss, R. (1968-07-01). "The crystal and molecular structure of trimeric bis(acetylacetonato)zinc(II)". Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry. 24 (7): 904–913. doi:10.1107/S0567740868003390. ISSN   0567-7408.
  3. 1 2 3 Barta, Nancy S.; Stille, John R. (2001-04-15), "Bis(acetylacetonato)zinc(II)", in John Wiley & Sons, Ltd (ed.), Encyclopedia of Reagents for Organic Synthesis, Chichester, UK: John Wiley & Sons, Ltd, pp. rb097, doi:10.1002/047084289x.rb097, ISBN   978-0-471-93623-7 , retrieved 2023-03-06
  4. "zinc;(Z)-4-oxopent-2-en-2-olate". pubchem.ncbi.nlm.nih.gov.
  5. Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. ISBN   978-0-08-037941-8.
  6. W. Clegg (2016). Private Communication. Cambridge Crystallographic Data Centre. doi:10.5517/ccdc.csd.cc1mcf4k.
  7. H. Montgomery, E. C. Lingafelter (1963). "The crystal structure of monoaquobisacetylacetonatozinc". Acta Crystallographica. 16 (8): 748–752. doi:10.1107/S0365110X6300195X.
  8. P. Harbach, H.-W. Lerner, M. Bolte (2003). "Diaquadiacetylacetonatozinc(II)". Acta Crystallographica Section e Structure Reports Online. 59 (9): m724–m725. doi:10.1107/S1600536803015848.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  9. Sigma-Aldrich Co. , product no. 480991 .
  10. Inubushi, Yoichi; Takami, Ryoji; Iwasaki, Mitsunobu; Tada, Hiroaki; Ito, Seishiro (April 1998). "Mechanism of Formation of Nanocrystalline ZnO Particles through the Reaction of [Zn(acac)2] with NaOH in EtOH". Journal of Colloid and Interface Science. 200 (2): 220–227. Bibcode:1998JCIS..200..220I. doi:10.1006/jcis.1997.5354.