Tris(acetylacetonato)iron(III): Difference between revisions

|Watchedfields = changed

|verifiedrevid = 444564832

|ImageFile1 = Tris(acetylacetonato)iron(III)-2D-by-AHRLS-2012.png

|ImageSize1 = 150px

|ImageFile2 = Iron acetylacetonate complex ball.png

|ImageSize2 = 150px

|ImageFile3 = Sample of Fe(acac)3.JPG

|ImageSize3 = 150px

|IUPACName = Tris(2,4-dioxopentan-3-ido-κ²''O'',''O''′)iron

|OtherNames = Iron(III) acetylacetonate, Iron(III) tris(2,4-pentanedionato), Fe(acac)₃

|Section1={{Chembox Identifiers

|CASNo = 14024-18-1

|CASNo_Ref = {{cascite|correct|CAS}}

|UNII_Ref = {{fdacite|correct|FDA}}

|UNII = 118BHF260P

|ChemSpiderID = 4588230

|EINECS = 237-853-5

|PubChem = 139087805

|SMILES = CC(=C[C-](C)O1)O[Fe+3]123(OC(=C[C-](C)O2)C)OC(=C[C-](C)O3)C

|StdInChI=1S/3C5H8O2.Fe/c3*1-4(6)3-5(2)7;/h3*3,6H,1-2H3;/q;;;+3/p-3/b3*4-3-;

|StdInChIKey = AQBLLJNPHDIAPN-LNTINUHCSA-K

|Section2={{Chembox Properties

|Formula = Fe(C₅H₇O₂)₃

|Appearance = Red Solid

|Density = 1.348 g/cm³

|MolarMass = 353.17 g/mol

|MeltingPtC = 180 to 181

|BoilingPt = decomposes

|Solubility = 2 g/L

}}

|Section7={{Chembox Hazards

|GHSPictograms = {{GHS05}} {{GHS07}}

|GHSSignalWord = Danger

|HPhrases = {{H-phrases|H302 + H312 + H332 | H318}}

|PPhrases = {{P-phrases|P261 | P280 | P301 + P312 | P302 + P352 + P312 | P304 + P340 + P312 | P305 + P351 + P338}}

|GHS_ref = <ref>GHS: [https://www.sigmaaldrich.com/NL/en/product/aldrich/517003 Sigma-Aldrich 517003] </ref>

}}

}}

[[File:IR Spectrum of Tris(acetylacetonato)iron(III).png|thumb|Infrared spectrum of Tris(acetylacetonato)iron(III)]]

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

Fe(acac)₃ is prepared by treating freshly precipitated Fe(OH)₃ with [[acetylacetone]].<ref>{{US patent reference| number = 2004127690| y = 2004| m = 07| d = 01| inventor = Chaudhari, Mihir Kanti et al.| title = Process for making metal acetylacetonates}}</ref>

:Fe(OH)₃ + 3 HC₅H₇O₂ → Fe(C₅H₇O₂)₃ + 3 H₂O

Fe(acac)₃ is an octahedral complex with six equivalent Fe-O bonds with bond distances of about 2.00 Å. The regular geometry is consistent with a [[Spin states (d electrons)|high-spin]] Fe³⁺ core with sp3d2 hyberdisation. As the metal orbitals are all evenly occupied the complex is not subject to [[Jahn–Teller effect|Jahn-Teller distortions]] and thus adopts a D₃ [[molecular symmetry]]. In contrast, the related metal acetylacetonate Mn(acac)₃ adopts a more distorted octahedral structure.<ref>{{cite journal | title = The infrared absorption spectra of metal acetylacetonates. | author = Lawson, K.E. | journal = Spectrochimica Acta | year = 1961 | volume = 17 | issue = 3| pages = 248–258 | doi = 10.1016/0371-1951(61)80071-4| bibcode = 1961AcSpe..17..248L }}</ref> The 5 unpaired ''d''-electrons also result in the complex being [[paramagnetic]], with a [[magnetic moment]] of 5.90 μ_B.

Fe(acac)₃ possesses [[helical chirality]]. The Δ- and Λ-[[enantiomer]]s slowly inter-convert via [[Bailar twist|Bailar]] and [[Ray–Dutt twist]]s. The rate of interconversion is sufficiently slow to allow its enantiomers to be partially resolved.<ref>Anders Lennartson "Optical resolution and racemisation of [Fe(acac)₃]" Inorganica Chimica Acta 2011, vol. 365, pp. 451–453. {{doi|10.1016/j.ica.2010.07.066}}</ref>

==Reactions==

Fe(acac)₃ has been examined as a precatalyst and reagent in organic chemistry, although the active iron-containing species is usually unidentified in these processes. In one instance, Fe(acac)₃ was shown to promote cross-coupling a [[diene]] to an [[olefin]].<ref>{{cite journal| title = Iron-Catalyzed Aminohydroxylation of Olefins|author1=Takacs, J. A., L. |author2=Madhavan, G.V. |author3=Creswell, M. |author4=Seely, F. |author5=Devroy, W. | journal = Organometallics| year = 1986| volume = 5| issue = 11| pages = 2395–2398| doi = 10.1021/om00142a044}}</ref> Fe(acac)₃ catalyzes the dimerization of [[isoprene]] to a mixture of 1,5-dimethyl-1,5-cyclooctadiene and 2,5-dimethyl-1,5-cyclooctadiene.<ref>{{cite journal| title = Oligomerization of isoprene by cobalt or iron complex catalysts| author = Misono, A.| journal = Bulletin of the Chemical Society of Japan| year = 1966| volume = 39| issue = 11| pages = 2425–2429| doi=10.1246/bcsj.39.2425 | doi-access = free}}</ref>

| title = Highly efficient catalysts-acetylacetonato complexes of transition metals in the 4th period for ring-opening polymerization of 1,3-benzoxazine| first3 = Takeshi| last3 = Endo| first2 = Shoji| last2 =Hirayama | author = Sudo, A.| journal = Journal of Polymer Science Part A: Polymer Chemistry| year = 2010| volume = 48| issue = 2| pages = 479| doi = 10.1002/pola.23810| bibcode = 2010JPoSA..48..479S}}</ref> Beyond the area of polymerization, Fe(acac)₃ has been found to catalyze the reaction of [[oxaziridine|N-sulfonyl oxaziridines]] with olefins to form 1,3-oxazolidine products.<ref>{{cite journal| title = Iron-Catalyzed Aminohydroxylation of Olefins|author1=Williamson, K. T. |author2=Yoon, T. | journal = J. Am. Chem. Soc.| year = 2010| volume = 132| pmid = 20232850| issue = 13| pages = 4570–4571| pmc = 2857537| doi = 10.1021/ja1013536}}</ref>

{{Iron compounds}}

{{Acetylacetonate complexes}}

[[Category:Iron(III) compounds]]

[[Category:Iron complexes]]