Difference between revisions 6001601 and 6001602 on simplewiki

{{chembox
| Watchedfields = changed
| verifiedrevid = 310175235
| ImageFileL1 = Ferrocene-2D.png
| ImageSizeL1 = 80 px
| ImageFileR1 = Ferrocene-from-xtal-3D-balls.png
| ImageSizeR1 = 120 px
| ImageFile2 = Photo of Ferrocene (powdered).JPG
(contracted; show full)|journal = [[Journal of Organometallic Chemistry]]
|year = 1991
|volume = 403
|pages = 195–208
|doi = 10.1016/0022-328X(91)83100-I}}</ref> and [[scanning tunneling microscopy]].<ref>{{cite journal
|author = L. F. N. Ah Qune, K. Tamada, M. Hara
|title = Self-Assembling Properties of 11-Ferrocenyl-1-Undecanethiol on Highly Oriented Pyrolitic Graphite Characterized by Scanning Tunneling Microscopy
|journal = 
eE-Journal of Surface Science and Nanotechnology
|year = 2008
|volume = 6
|pages = 119–123
|doi = 10.1380/ejssnt.2008.119}}</ref><ref>[http://www.jstage.jst.go.jp/article/ejssnt/6/0/119/_pdf Self-Assembling Properties of 11-Ferrocenyl-1-Undecanethiol on Highly Oriented Pyrolitic Graphite Characterized by Scanning Tunneling Microscopy]</ref>

The carbon-carbon bond distances are 1.40 Å within the five membered rings, and the Fe-C bond distances are 2.04 Å.

(contracted; show full) organic solvents, such as benzene, but is insoluble in water. Ferrocene is an [[air]]-stable orange solid that readily [[Sublimation (physics)|sublime]]s, especially upon heating in a vacuum. It is stable to temperatures as high as 400 °C.<ref>Solomons, Graham, and Craig Fryhle. Organic Chemistry. 9th ed. USA: John Wiley & Sons, Inc., 2006.</ref> The following table gives typical values of vapor pressure of ferrocene at different temperatures:<ref>{{cite journal|doi=10.1021/je050502y
|title=New Static Apparatus and Vapor Pressure of Reference Materials:  Naphthalene, Benzoic Acid, Benzophenone, and Ferrocene|year=2006|last1=Monte|first1=Manuel J. S.|last2=Santos|first2=Luís M. N. B. F.|last3=Fulem|first3=Michal|last4=Fonseca|first4=José M. S.|last5=Sousa|first5=Carlos A. D.|journal=Journal of Chemical & Engineering Data|volume=51|pages=757}}</ref>

{| class="wikitable"
|-
! pressure(Pa)
! 1
! 10
! 100
(contracted; show full)

==Derivatives and variations==
Many other hydrocarbons can be used instead of cyclopentadienyl. For example, [[indene|indenyl]] can be used in place of the cyclopentadienyl to form bisbenzoferrocene.<ref>{{cite journal|doi=10.1016/S0020-1693(99)00123-1
|title=Novel organoiron compounds resulting from the attempted syntheses of dibenzofulvalene complexes|year=1999|last1=Waldbaum|first1=B|journal=Inorganica Chimica Acta|volume=291|pages=109}}</ref>

[[Image:FcVarietyPack.png|400px|center|Various ferrocene derivatives where cyclopentadienyl has been replaced by related ligands]]

The carbon atoms can be replaced by heteroatoms as illustrated by [[Fe(η<sup>5</sup>-C<sub>5</sub>Me<sub>5</sub>)(η<sup>5</sup>-P<sub>5</sub>]] and [[Fe(η<sup>5</sup>-C<sub>5</sub>H<sub>5</sub>)(η<sup>5</sup>-C<sub>4</sub>H<sub>4</sub>N)]] ("azaferrocene"). The latter arises from decarbonylation of [[Fe(η<sup>5</sup>-C<sub>5</sub>H<sub>5</sub>)(CO)<sub>2</sub>(η<sup>1</sup>-pyrrole)]] in [[cyclohexane]].(a.<ref>{{cite journal|doi=10.1016/0022-328X(90)85359-7}}</ref> This compound on boiling under [[reflux]] in [[benzene]] is converted to ferrocene.<ref>{{cite journal|doi=10.1021/ic00133a006|title=An improved photochemical synthesis of azaferrocene|year=1990|last1=Zakrzewski|first1=J|journal=Journal of Organometallic Chemistry|volume=388|pages=175}}</ref> This compound on boiling under [[reflux]] in [[benzene]] is converted to ferrocene.<ref>{{cite journal|doi=10.1021/ic00133a006|title=Chemistry of some .eta.5-pyrrolyl- and .eta.1-N-pyrrolyliron complexes|year=1982|last1=Efraty|first1=Avi.|last2=Jubran|first2=Nusrallah.|last3=Goldman|first3=Alexander.|journal=Inorganic Chemistry|volume=21|pages=868}}</ref>

Because of the ease of substitution, many structurally unusual ferrocene derivatives have been prepared. For example, the penta(ferrocenyl)cyclopentadienyl ligand,<ref>{{cite journal|author=Y. Yu, A.D. Bond, P. W. Leonard, K. P. C. Vollhardt, G. D. Whitener| title=Syntheses, Structures, and Reactivity of Radial Oligocyclopentadienyl Metal Complexes: Penta(ferrocenyl)cyclopentadienyl and Congeners| journal= [[Angewandte Chemie International Edition]]| volume =45|issue=11| pages= 1794–17(contracted; show full)[[pl:Ferrocen]]
[[ru:Ферроцен]]
[[fi:Ferroseeni]]
[[sv:Ferrocen]]
[[th:เฟอร์โรซีน]]
[[tr:Ferrosen]]
[[ur:Ferrocene]]
[[zh:二茂铁]]