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User:Barras/Ferrocene
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 457631192
| ImageFileL1 = Ferrocene.svg
| ImageSizeL1 = 80 px
| ImageFileR1 = Ferrocene-from-xtal-3D-balls.png
| ImageSizeR1 = 80 px
| ImageFileL2 = Ferrocene 3d model 2.png
| ImageFileR2 = Photo of Ferrocene (powdered).JPG
| IUPACName = ferrocene, bis(''η''<sup>5</sup>-cyclopentadienyl)iron
| OtherNames = dicyclopentadienyl iron ⏎
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| InChIKey = KTWOOEGAPBSYNW-UHFFFAOYAZ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/2C5H5.Fe/c2*1-2-4-5-3-1;/h2*1-5H;/q2*-1;+2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = KTWOOEGAPBSYNW-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
(contracted; show full)

[[Robert Burns Woodward]] and [[Geoffrey Wilkinson]] deduced the structure based on its reactivity.<ref>{{cite journal |first1= G. |last1=Wilkinson|author1-link=Geoffrey Wilkinson |first2=M.|last2= Rosenblum |first3=M. C.|last3= Whiting
|first4= R. B. |last4=Woodward|author4-link=Robert Burns Woodward |title = The Structure of Iron Bis-Cyclopentadienyl |journal = [[Journal of the American Chemical Society|J. Am. Chem. Soc.]] |year = 1952|volume = 74 |pages = 2125–2126 |doi = 10.1021/ja01128a527 |issue = 8}}</ref> Independently [[Ernst Otto Fischer]] also came to the conclusion of the sandwich structure and started to synthesize other metallocenes such as [[nickelocene]] and [[cobaltocene]].<ref>{{cite journal |author1-link=Ernst Otto Fischer|first1 = E. O.|last1= Fischer|first2= W. |last2=Pfab |title = Zur Kristallstruktur der Di-Cyclopentadienyl-Verbindungen des zweiwertigen Eisens, Kobalts und Nickels|trans-title=On the crystal structure of the bis-cyclopentadienyl compounds of divalent iron, cobalt and nickel |journal = [[Zeitschrift für Naturforschung B]] |year = 1952 |volume = 7 |pages = 377–379 |doi =}}</ref>⏎

The structure of ferrocene was confirmed by [[Nuclear magnetic resonance|NMR]] spectroscopy and [[X-ray crystallography]].<ref name=r1/><ref>{{cite journal|last1=Dunitz|first1= J. D.|last2= Orgel|first2= L. E.|title=Bis-Cyclopentadienyl&nbsp;– A Molecular Sandwich|journal= [[Nature (journal)|Nature]] |year=1953| volume=171 |pages= 121–122|doi = 10.1038/171121a0|issue=4342|bibcode = 1953Natur.171..121D }}</ref><ref>{{cite journal |first1= J.|last1= Dunitz|first2= L.|last2= Orgel|(contracted; show full)
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[[Category:Organoiron compounds]]
[[Category:Metallocenes]]
[[Category:Antiknock agents]]
[[Category:Sandwich compounds]]
[[Category:Cyclopentadienyl complexes]]