3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||224.50 g/mol|
|Appearance||Brown yellow solid|
|Melting point||205 °C (401 °F; 478 K) decomposes|
|Main hazards||considered nonhazardous|
|Safety data sheet|||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
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.
With a 1:2 stoichiometric ratio of palladium atoms and acetate ligands, the compound exists as molecular and polymeric forms. Pd achieves approximate square planar coordination in both forms.
As prepared by Wilkinson and coworkers in 1965 and later characterized by Skapski and Smart in 1970 by single crystal X-ray diffraction, palladium(II) acetate is a red-brown solid that crystallizes as monoclinic plates. It has a trimeric structure, consisting of an equilateral triangle of Pd atoms each pair of which is bridged with two acetate groups in a butterfly conformation.
Palladium(II) acetate can also be prepared as a pale pink form. According to X-ray powder diffraction, this form is polymeric.
Palladium acetate, in trimeric form, can be prepared by treating palladium sponge with a mixture of acetic acid and nitric acid. An excess of palladium sponge metal or nitrogen gas flow are required to prevent contamination by the mixed nitrito-acetate (Pd3(OAc)5NO2).
Relative to the trimeric acetate, the mixed nitrate-acetate variant has different solubility and catalytic activity. Preventing, or controlling for the amount of, this impurity can be an important aspect for reliable use of palladium(II) acetate.
Palladium(II) propionate is prepared analogously; other carboxylates are prepared by treating palladium(II) acetate with the appropriate carboxylic acid. Likewise, palladium(II) acetate can be prepared by treating other palladium(II) carboxylates with acetic acid. This ligand exchange starting with a purified other carboxylate is an alternative way to synthesize palladium(II) acetate free from the nitro contaminant.
When warmed with alcohols, or on prolonged boiling with other solvents, palladium(II) acetate decomposes to palladium.
Palladium acetate is a catalyst for many organic reactions, especially alkenes, dienes, and alkyl, aryl, and vinyl halides to form reactive adducts.
Reactions catalyzed by palladium(II) acetate:
Pd(O2CCH3)2 is compatible with the electronic properties of aryl bromides, and unlike other methods of synthesis, this method does not require high pressure equipment.
Palladium acetate is used to produce other palladium(II) compounds. For example, phenylpalladium acetate, used to isomerize allyl alcohols to aldehydes, is prepared by the following reaction:
Acetyl halides and salts of the acetate ion