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Decamethylferrocene information


Decamethylferrocene
Names
Preferred IUPAC name
Decamethylferrocene
Other names
  • Bis(η5-pentamethylcyclopentadienyl)iron(II)
  • Decamethyl-ferrocene
  • 1,1′,2,2′,3,3′,4,4′,5,5′-Decamethyl-ferrocene
  • Bis(pentamethylcyclopentadienyl)iron(II)
  • Permethylferrocene
Identifiers
CAS Number
  • 12126-50-0 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 4321548 ☒N
ECHA InfoCard 100.116.086 Edit this at Wikidata
PubChem CID
  • 5148079
CompTox Dashboard (EPA)
  • DTXSID80923743 Edit this at Wikidata
InChI
  • InChI=1S/2C10H15.Fe/c2*1-6-7(2)9(4)10(5)8(6)3;/h2*1-5H3;/q2*-1;+2 ☒N
    Key: SEYZDJPFVVXSRB-UHFFFAOYSA-N ☒N
  • InChI=1/2C10H15.Fe/c2*1-6-7(2)9(4)10(5)8(6)3;/h2*1-5H3;/q2*-1;+2
    Key: SEYZDJPFVVXSRB-UHFFFAOYAP
SMILES
  • C[c-]1c(c(c(c1C)C)C)C.C[c-]1c(c(c(c1C)C)C)C.[Fe+2]
Properties
Chemical formula
C20H30Fe
Molar mass 326.305 g·mol−1
Appearance Yellow crystalline solid[1]
Melting point 291 to 295 °C (556 to 563 °F; 564 to 568 K)[1]
Sublimation
conditions
413 K, 5.3 Pa[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Decamethylferrocene or bis(pentamethylcyclopentadienyl)iron(II) is a chemical compound with formula Fe(C5(CH3)5)2 or C20H30Fe. It is a sandwich compound, whose molecule has an iron(II) cation Fe2+ attached by coordination bonds between two pentamethylcyclopentadienyl anions (Cp*, (CH3)5C5). It can also be viewed as a derivative of ferrocene, with a methyl group replacing each hydrogen atom of its cyclopentadienyl rings. The name and formula are often abbreviated to DmFc,[3] Me10Fc [4] or FeCp*2.[5]

This compound is a yellow crystalline solid that is used in chemical laboratories as a weak reductant. The iron(II) core is easily oxidized to iron(III), yielding the monovalent cation decamethylferrocenium, and even to higher oxidation states.[5]

  1. ^ a b Cite error: The named reference King was invoked but never defined (see the help page).
  2. ^ Cite error: The named reference Con was invoked but never defined (see the help page).
  3. ^ Torriero, Angel A. J. (2014). "Characterization of decamethylferrocene and ferrocene in ionic liquids: argon and vacuum effect on their electrochemical properties". Electrochimica Acta. 137: 235–244. doi:10.1016/j.electacta.2014.06.005.
  4. ^ Noviandri, Indra; Brown, Kylie N.; Fleming, Douglas S.; Gulyas, Peter T.; Lay, Peter A.; Masters, Anthony F.; Phillips, Leonidas (1 August 1999). "The Decamethylferrocenium/Decamethylferrocene Redox Couple: A Superior Redox Standard to the Ferrocenium/Ferrocene Redox Couple for Studying Solvent Effects on the Thermodynamics of Electron Transfer". The Journal of Physical Chemistry B. 103 (32): 6713–6722. doi:10.1021/jp991381+. ISSN 1520-6106.
  5. ^ a b Malischewski, M.; Adelhardt, M.; Sutter, J.; Meyer, K.; Seppelt, K. (2016). "Isolation and structural and electronic characterization of salts of the decamethylferrocene dication". Science. 353 (6300): 678–682. Bibcode:2016Sci...353..678M. doi:10.1126/science.aaf6362. PMID 27516596. S2CID 43385610.

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Decamethylferrocene

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