1024:'''Decamethylferrocene''' or '''bis(pentamethylcyclopentadienyl)iron(II)''' is a ] with formula {{chem2|Fe(C5(CH3)5)2}} or {{chem2|C20H30Fe}}. It is a ], whose molecule has an ] cation {{chem2|Fe(2+)}} attached by ]s between two ] anions ({{chem2|Cp\*(-)}}, {{chem2|(CH3)5C5(-)}}). It can also be viewed as a derivative of ], with a ] replacing each ] atom of its ] rings. The name and formula are often abbreviated to '''DmFc''',<ref name=torri>{{cite journal | year = 2014 | title = Characterization of decamethylferrocene and ferrocene in ionic liquids: argon and vacuum effect on their electrochemical properties | journal = Electrochimica Acta | volume = 137 | pages = 235β244 | doi = 10.1016/j.electacta.2014.06.005 | last1 = Torriero | first1 = Angel A. J.}}</ref> {{chem2|Me10Fc}} <ref name=novi>{{cite journal |last1=Noviandri |first1=Indra |last2=Brown |first2=Kylie N. |last3=Fleming |first3=Douglas S. |last4=Gulyas |first4=Peter T. |last5=Lay |first5=Peter A. |last6=Masters |first6=Anthony F. |last7=Phillips |first7=Leonidas |title=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 |journal=The Journal of Physical Chemistry B |date=1 August 1999 |volume=103 |issue=32 |pages=6713β6722 |doi=10.1021/jp991381+ |issn=1520-6106}}</ref> or {{chem2|FeCp\*2}}.<ref name=malis>{{cite journal | year = 2016 | title = Isolation and structural and electronic characterization of salts of the decamethylferrocene dication | journal = Science | volume = 353 | issue = 6300| pages = 678β682 | doi = 10.1126/science.aaf6362 | pmid = 27516596 | last1 = Malischewski | first1 = M. | last2 = Adelhardt | first2 = M. | last3 = Sutter | first3 = J. | last4 = Meyer | first4 = K. | last5 = Seppelt | first5 = K. | bibcode = 2016Sci...353..678M | s2cid = 43385610 }}</ref>
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Using powerful oxidants (e.g. {{chem2|SbF5}} or {{chem2|AsF5}} in {{chem2|SO2}}, or {{chem2|XeF(+)/Sb2F11(-)}} in {{chem2|HF/SbF5}}) decamethylferrocene is oxidized to a stable dication with an iron(IV) core. In the {{chem2|Sb2F11(-)}} salt, the {{chem2|Cp\*}} rings are parallel. In contrast, a tilt
1120:| journal = ] | doi = 10.1016/S0022-328X(00)91042-8 | title = Organometallic Chemistry of the Transition Metals XXI. Some Ο-pentamethylcyclopentadienyl Derivatives of Various Transition Metals | year = 1967 | volume = 8 | issue = 2 | pages = 287β297}}</ref>
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This compound is a yellow crystalline solid that is used in chemical laboratories as a weak ]. The iron(II) core is easily ] to iron(III), yielding the monovalent cation '''decamethylferrocenium''', and even to higher oxidation states.<ref name =
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M. B. | journal = ] | doi = 10.1016/S0022-328X(00)91042-8 | title = Organometallic
Chemistry of the Transition Metals XXI. Some Ο-pentamethylcyclopentadienyl Derivatives of Various Transition Metals | year = 1967 | volume = 8 | issue = 2 | pages =
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Like ferrocene, decamethylferrocene forms a stable cation because Fe(II) is easily oxidized to Fe(III). Because of the electron donating methyl groups on the Cp* groups, decamethylferrocene is more reducing than is ferrocene. In a solution of
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title = Chemical Redox Agents for
Organometallic Chemistry | journal= ] | volume = 96 | year = 1996 | pages = 877β910 | doi = 10.1021/cr940053x | pmid=11848774}}</ref> Oxygen is reduced to ] by decamethylferrocene in acidic
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Decamethylferrocene is prepared in the same manner as ferrocene from ]. This method can be used to produce other decamethylcyclopentadienyl sandwich compounds.<ref name=King>{{cite journal |
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Decamethylferrocene is prepared in the same manner as ferrocene from ]. This method can be used to produce other decamethylcyclopentadienyl sandwich compounds.<ref name=King>{{cite journal |
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1033:'''Decamethylferrocene''' is a ]. In terms of structure and bonding it resembles ], but with a ] on each of the carbons of the Cp rings. It is a yellow crystalline solid that is a weak ].
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1217:* has staggered Cp* rings. The average distance between iron and each carbon is approximately 2.050 Γ
. This structure has been confirmed by ].<ref name=Frey>{{cite journal |
1192::2 Li(C<sub>5</sub>Me<sub>5</sub>) + FeCl<sub>2</sub> β Fe(C<sub>5</sub>Me<sub>5</sub>)<sub>2</sub> + 2 LiCl
1185::2 Li(C<sub>5</sub>Me<sub>5</sub>) + FeCl<sub>2</sub> β Fe(C<sub>5</sub>Me<sub>5</sub>)<sub>2</sub> + 2 LiCl
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rings. The average distance between iron and each carbon is approximately 2.050 Γ
. This structure has been confirmed by ].<ref name=Frey>{{cite journal |
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Like ferrocene, decamethylferrocene forms a stable cation because Fe(II) is easily oxidized to Fe(III). Because of the electron donating methyl groups on the
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1546:| pages = 877β910 | doi = 10.1021/cr940053x | pmid=11848774}}</ref> Oxygen is reduced to ] by decamethylferrocene in acidic solution.<ref>
1374:| title = Crystal and molecular structures of decamethylmanganocene and decamethylferrocene. Static Jahn-Teller distortion in a metallocene |
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angle of 17Β° between the {{chem2|Cp\*}} rings is observed in the crystal structure of the {{chem2|SbF6(-)}} salt.<ref name=malis/>
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E. |title = Chemical Redox Agents for
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groups, decamethylferrocene is more reducing than is ferrocene. In a solution of
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Oxygen and proton reduction by decamethylferrocene in non-aqueous acidic media
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Oxygen and proton reduction by decamethylferrocene in non-aqueous acidic media
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842:|StdInChI = 1S/2C10H15.Fe/c2*1-6-7(2)9(4)10(5)8(6)3;/h2*1-5H3;/q2*-1;+2
798:|InChI = 1/2C10H15.Fe/c2*1-6-7(2)9(4)10(5)8(6)3;/h2*1-5H3;/q2*-1;+2
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1522:(β0.48 V vs Fc/{{chem2|Fc(+)}} in {{chem2|CH2Cl2}})
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Appearance = Yellow crystalline solid<ref name=King/>
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CH<sub>2</sub>Cl<sub>2</sub>,
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1686:reference.<ref name=Con>{{cite journal |
767:|SMILES = C1c(c(c(c1C)C)C)C.C1c(c(c(c1C)C)C)C.
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864:|StdInChIKey = SEYZDJPFVVXSRB-UHFFFAOYSA-N
236:Latest revision as of 09:15, 29 June 2024
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974:= 413 K, 5.3 Pa<ref name=Con/>
785:= 413 K, 5.3 Pa<ref name=Con/>
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458:OtherNames = Decamethyl-ferrocene
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525:-Decamethyl-ferrocene
482:-Decamethyl-ferrocene
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1645:==Redox reactions==
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1793:== References ==
1786:== References ==
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1728:Corminboeuf
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1668:<sup>
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1559:|first3=Pei
1141:Preparation
783:Sublimation
294:Visual edit
195:Rollbackers
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1413:Kenneth N.
1059:malis/>
752:291-295 Β°C
748:Melting Pt
253:AnDeargMor
96:Revision 2
53:Revision 1
1738:, M. and
1562:Yu|last4=
1520:reference
1429:James C.
1389:= Derek P
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180:contribs
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