Revision 6001544 of "User:Barras/Ferrocene" on simplewiki

{{Chembox new
| ImageFileL1 = Ferrocene-2D.png
| ImageSizeL1 = 80 px
| ImageFileR1 = Ferrocene-3D-balls-B.png
| ImageSizeR1 = 120 px
| IUPACName = ferrocene, bis(η<sup>5</sup>-cyclopentadienyl)iron
| OtherNames = ferrocene, iron cyclopentadienyl 
| Section1 = {{Chembox Identifiers
|   CASNo = 102-54-5
|   PubChem = 11985121
|   SMILES = 
  }}
| Section2 = {{Chembox Properties
|   Formula = C<sub>10</sub>H<sub>10</sub>Fe
|   MolarMass = 186.04 g/mol
|   Appearance = light orange powder
|   Density = 2.69 g/cm<sup>3</sup> (20 °C)
|   MeltingPt = 174 °C
|   BoilingPt = 249 °C
|   Solubility = Insoluble in water, soluble in most organic solvents
  }}
| Section3 = {{Chembox Hazards
|   MainHazards = 
|   FlashPt = 
|   Autoignition = 
  }}
| Section8 = {{Chembox Related
| OtherCpds = [[cobaltocene]], [[nickelocene]], [[chromacene]], [[bis(benzene)chromium]]}}
}}

'''Ferrocene''' is the [[organometallic compound]] with the formula Fe(C<sub>5</sub>H<sub>5</sub>)<sub>2</sub>.  It is the prototypical [[metallocene]], a type of [[organometallic chemistry|organometallic]] [[chemistry|chemical]] compound consisting of two [[cyclopentadienyl complex|cyclopentadienyl]] rings bound on opposite sides of a central [[metal]] atom.  Such organometallic compounds are also known as [[sandwich compound]]s.<ref>{{cite journal|author=R. Dagani |url=http://pubs.acs.org/isubscribe/journals/cen/79/i49/html/7949sci1.html | title=Fifty Years of Ferrocene Chemistry| journal=[[Chemical and Engineering News]] |date=3 December 2001|volume= 79 |issue= 49 | pages = 37–38 |format=Subscription required}}</ref>  The rapid growth of [[organometallic chemistry]] is often attributed to the excitement arising from the discovery of ferrocene and its many analogues.

==History==
Ferrocene, like many chemical compounds, was first prepared unintentionally.  In 1951, Pauson and Kealy at [[Duquesne University]] reported the reaction of cyclopentadienyl magnesium bromide and [[iron(III) chloride|ferric chloride]] with the goal of oxidatively coupling the diene to prepare [[fulvalene]]. Instead, they obtained a light orange powder of "remarkable stability."<ref>{{cite journal
 | author = T. J. Kealy, P. L. Pauson
 | title = A New Type of Organo-Iron Compound
 | journal = Nature
 | year = 1951 
 | volume = 168 
 | pages = 1039
 | doi = 10.1038/1681039b0}}</ref> This stability was accorded to the aromatic character of the negative charged cyclopentadienyls, but the sandwich structure of the η<sup>5</sup> (pentahapto) compound was not recognized by them. 

[[Robert Burns Woodward]] and [[Geoffrey Wilkinson]] deduced the structure based on its reactivity.<ref>{{cite journal
 | author = G. Wilkinson, M. Rosenblum, M. C. Whiting, R. B. Woodward
 | title = The Structure of Iron Bis-Cyclopentadienyl
 | journal = [[Journal of the American Chemical Society]]
 | year = 1952
 | volume = 74
 | pages = 2125–2126
 | doi = 10.1021/ja01128a527}}</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
 | author = E. O. Fischer, W. Pfab
 | title = Zur Kristallstruktur der Di-Cyclopentadienyl-Verbindungen des zweiwertigen Eisens, Kobalts und Nickels 
 | journal = Z. Naturforsch. B
 | year = 1952
 | volume = 7
 | pages = 377–379
 | doi = }}</ref>  Ferrocene's structure was confirmed by [[Nuclear magnetic resonance|NMR]] spectroscopy and [[X-ray crystallography]].<ref>{{cite journal
 | author = J. Dunitz, L. Orgel, A. Rich
 | title = The crystal structure of ferrocene
 | journal = [[Acta Crystallographica]]
 | year = 1956
 | volume = 9
 | pages = 373–5
 | doi = 10.1107/S0365110X56001091}}</ref><ref>{{cite journal
 | author = Pierre Laszlo, Roald Hoffmann,
 | title = Ferrocene: Ironclad History or Rashomon Tale?
 | journal = Angewandte Chemie International Edition
 | year = 2000
 | volume = 39
 | pages = 123–124
 | doi = 10.1002/(SICI)1521-3773(20000103)39:1<123::AID-ANIE123>3.0.CO;2-Z}}</ref> Its distinctive "sandwich" structure led to an explosion of interest in compounds of [[d-block]] metals with hydrocarbons, and invigorated the development of the flourishing study of organometallic chemistry.  In 1973 [[Ernst Otto Fischer|Fischer]] of the [[Ludwig-Maximilians-Universität München]] and [[Geoffrey Wilkinson|Wilkinson]] of [[Imperial College London]] shared a Nobel Prize  with for their work on metallocenes and other aspects of organometalic chemistry.<ref>{{cite web |url=http://nobelprize.org/nobel_prizes/chemistry/laureates/1973/press.html |title= Press Release: The Nobel Prize in Chemistry 1973 |year= 1973 |publisher= The Royal Swedish Academy of Sciences}}</ref>

==Bonding and Structure==
The iron atom in ferrocene is normally assigned to the +2 oxidation state, as can be shown using [[Mössbauer spectroscopy]]. Each cyclopentadienyl (Cp) ring is then allocated a single negative charge, bringing the number of π-electrons on each ring to six, and thus making them [[aromaticity|aromatic]].  These twelve electrons (six from each ring) are then shared with the metal ''via'' covalent bonding, which, when combined with the six ''d''-electrons on Fe<sup>2+</sup>, results in the complex having an [[18-electron rule|18-electron]], [[noble gas]] electron configuration.  

The lack of individual bonds between the carbon atoms of the Cp ring and the Fe<sup>2+</sup> ion results in the Cp rings to freely rotate about the Cp<sub>(centroid)</sub>-Fe-Cp<sub>(centroid)</sub> axis, as observed by [[Nuclear Magnetic Resonance]]<ref>{{cite journal
 | author = E. W. Abel, N. J. Long, K. G. Orrell, A. G. Osborne, V. Sik
 | title = Dynamic NMR studies of ring rotation in substituted ferrocenes and ruthenocenes
 | 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 = [[e-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 bond distances between the sandwiched iron and the carbons of the rings are 2.04 Å.

==Physical properties==
Ferrocene is an [[air]]-stable orange solid that readily [[Sublimation (physics)|sublime]]s, especially upon heating in a vacuum.  As expected for a symmetric and uncharged species, ferrocene is soluble in normal organic solvents, such as benzene, but is insoluble in water.  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>Monte, M. J. S.; Santos, L. M. N. B. F.; Fulem, M.; Fonseca, J. M. S. & Sousa, C. A. D.,  New static apparatus and vapor pressure of reference materials: Naphthalene, benzoic acid, benzophenone, and ferrocene,  [[J. Chem. Eng. Data]], 2006, 51, 757-766</ref>

{| class="wikitable"
|-
! pressure(Pa)
! 1
! 10
! 100
|-
| temperature(K)
| 298
| 323
| 353
|}

==Chemical properties==

Ferrocene is efficiently prepared by the reaction of sodium cyclopentadienyl with anhydrous [[iron(II) chloride|ferrous chloride]] in ethereal solvents:
:2 NaC<sub>5</sub>H<sub>5</sub>  +  FeCl<sub>2</sub>   →   Fe(C<sub>5</sub>H<sub>5</sub>)<sub>2</sub>  +  2 NaCl

===Reaction with electrophiles===

Ferrocene undergoes many reactions characteristic of aromatic compounds, enabling the preparation of substituted derivatives.  A common undergraduate experiment is the [[Friedel-Crafts reaction]] of ferrocene with [[acetic anhydride]] (or [[acetyl chloride]]) in the presence of [[phosphoric acid]] as a catalyst.  The preparation of phosphorus derivatives of ferrocenes are illustrative.  In the presence of [[aluminium chloride]]  Me<sub>2</sub>NPCl<sub>2</sub> and ferrocene react to give ferrocenyl dichloro[[phosphine]],<ref>{{cite journal
 | title = Ferrocene derivatives. 27. Ferrocenyldimethylphosphine
 | author = G.R. Knox, P.L. Pauson and D. Willison
 | journal = Organometallics
 | volume = 11
 | issue = 8
 | pages = 2930 &ndash; 2933
 | year = 1992
 | doi = 10.1021/om00044a038
}}</ref>
while treatment with [[phenyldichlorophosphine]] under similar conditions forms ''P,P''-diferrocenyl-''P''-phenyl phosphine.<ref>{{cite journal
 | author = G.P. Sollott, H.E. Mertwoy, S. Portnoy and J.L. Snead
 | title = Unsymmetrical Tertiary Phosphines of Ferrocene by Friedel-Crafts Reactions. I. Ferrocenylphenylphosphines 
 | journal = J. Org. Chem.
 | year = 1963 
 | volume = 28 
 | pages = 1090 &ndash; 1092
 | doi = 10.1021/jo01039a055
}}</ref>
In common with [[anisole]] the reaction of ferrocene with P<sub>4</sub>S<sub>10</sub> forms a dithiadiphosphetane disulfide.<ref>{{cite journal
 | title = 2,4-Diferrocenyl-1,3-dithiadiphosphetane 2,4-disulfide; structure and reactions with catechols and [PtCl<sub>2</sub>(PR<sub>3</sub>)<sub>2</sub>](R = Et or Bun)
 | author = Mark R. St. J. Foreman, Alexandra M. Z. Slawin and J. Derek Woollins
 | journal = J. Chem. Soc., Dalton Trans., 
 | year = 1996
 | pages =  3653 &ndash; 3657
 | doi = 10.1039/DT9960003653
}}</ref>

[[Image:FcGen'l.png|400px|thumb|center|Important reactions of ferrocene with electrophiles and other reagents.]]

===Lithiation===

Ferrocene reacts readily with [[butyl lithium]] to give 1,1'-dilithioferrocene, which in turn is a versatile [[nucleophile]]. It has been reported that the reaction of 1,1'-dilithioferrocene with [[selenium]] diethyl[[dithiocarbamate]] forms a strained ferrocenophane where the two cyclopentadienyl ligands are linked by the selenium atom.<ref>Ron Rulkens, Derek P. Gates, David Balaishis, John K. Pudelski, Douglas F. McIntosh, Alan J. Lough, and Ian Manners, ''J. Am. Chem. Soc.'', 1997, '''119''', 10976</ref> This ferrocenophane can be converted to a polymer by a [[thermal]] [[ring-opening polymerization]] (ROP) to form poly(ferrocenyl selenide). Likewise by the reaction of [[silicon]] and [[phosphorus]] linked ferrocenophanes the poly(ferrocenylsilane)s and poly(ferrocenylphosphines)s can be obtained.<ref>Paloma Gómez-Elipe, Rui Resendes, Peter M. Macdonald, and Ian Manners, ''J. Am. Chem. Soc.,'' 1998, '''120''', 8348</ref><ref>Timothy J. Peckham, Jason A. Massey, Charles H. Honeyman, and Ian Manners, ''Macromolecules'', 1999, ''32'', 2830</ref>

[[Image:Ferrocenelithiation.png|450px|thumb|center|A diagram showing the litiation of ferrocene with BuLi, and then the reactions of the dilithioferrocene with a series of electrophiles]]

===Redox chemistry===
Unlike the majority of hydrocarbons, ferrocene undergoes a one-electron oxidation at a low potential, around 0.5 V ''vs''. a [[saturated calomel electrode]] (SCE). Some [[electron]] rich hydrocarbons (e.g., [[aniline]]) also are oxidized at low potentials, but only irreversibly. Oxidation of ferrocene gives a stable cation called ferrocenium. On a preparative scale, the oxidation is conveniently effected with FeCl<sub>3</sub> to give the blue-colored ion, [Fe(C<sub>5</sub>H<sub>5</sub>)<sub>2</sub>]<sup>+</sup>, which is often isolated as its [[hexafluorophosphate|PF<sub>6</sub><sup>−</sup>]] salt. Alternatively, [[silver nitrate]] may be used as the oxidizer.

Ferrocenium salts are sometimes used as oxidizing agents, in part because the product ferrocene is fairly inert and readily separated from ionic products.<ref>{{cite journal|author=N. G. Connelly, W. E. Geiger| title=Chemical Redox Agents for Organometallic Chemistry|journal=[[Chemical Reviews]]|date= 1996| volume= 96| pages= 877–910| doi=10.1021/cr940053x}}</ref>  Substituents on the cyclopentadienyl ligands alters the redox potential in the expected way: electron withdrawing group such as a carboxylic acid shift the potential in the [[anodic]] direction (''i.e.'' made more positive), whereas electron releasing groups such as [[methyl]] groups shift the potential in the [[cathodic]] direction (more negative). Thus, decamethylferrocene is much more easy to oxidise than ferrocene itself. Ferrocene is often used as an [[internal standard]] for calibrating redox potentials in non-aqeous [[electrochemistry]].

==Stereochemistry==
A variety of substitution patterns are possible with ferrocene including substition at one or both of the rings. The most common substitution patterns are 1-substituted (one substituent on one ring) and 1,1'-disubstituted (one substituent on each ring).  Usually the rings rotate freely, which simplifies the isomerism.  Disubstituted ferrocenes can exist as either 1,2- and 1,1' isomers, which are not interconvertable.  1,2-Heterodisubstituted ferrocenes are chiral.

==Applications of ferrocene and its derivatives==
Ferrocene and its numerous derivatives have no large-scale applications, but have many niche uses that exploit the unusual structure (ligand scaffolds, pharmaceutical candidates), robustness (anti-knock formulations, precursors to materials), and redox (reagents and redox standards).

===Fuel additives===
Ferrocene and its derivatives are [[antiknock agent]]s used in the fuel for petrol engines; they are safer than [[tetraethyl lead]], previously used.<ref>[http://www.osd.org.tr/14.pdf Application of fuel additives]</ref> It is possible to buy at [[Halfords]] in  the UK,  a petrol additive solution which contains ferrocene which can be added to unleaded petrol to enable it to be used in vintage cars which were designed to run on leaded petrol.<ref>{{US patent|4104036}}</ref> The iron containing deposits formed from ferrocene can form a conductive coating on the spark plug surfaces.

In [[diesel]]-fuelled engines, ferrocene reduces the production of soot.

===Pharmaceutical===
Some ferrocenium salts exhibit anticancer activity, and an experimental drug has been reported which is a ferrocenyl version of [[tamoxifen]].<ref name = top2003 /> The idea is that the tamoxifen will bind to the [[estrogen]] binding sites, resulting in a cytotoxicity effect.<ref>{{cite journal|journal=[[Chemical and Engineering News]] | date=16 Sep 2002| title= The Bio Side of Organometallics | author= Ron Dagani| volume = 80| issue= 37| pages = 23–29| url=http://pubs.acs.org/cen/science/8037/8037sci1.html}}</ref><ref>
{{cite journal|author=S. Top, B. Dauer, J. Vaissermann and G. Jaouen| journal=[[Journal of Organometallic Chemistry]]| title= Facile route to ferrocifen, 1-[4-(2-dimethylaminoethoxy)]-1-(phenyl-2-ferrocenyl-but-1-ene), first organometallic analogue of tamoxifen, by the McMurry reaction | doi=10.1016/S0022-328X(97)00086-7 |date=1997| volume=541| pages= 355–361}}</ref><ref name=top2003>{{cite journal|author=S. Top, A. Vessières, G. Leclercq, J. Quivy, J. Tang, J. Vaissermann, M. Huché and G. Jaouen| title=Synthesis, Biochemical Properties and Molecular Modelling Studies of Organometallic Specific Estrogen Receptor Modulators (SERMs), the Ferrocifens and Hydroxyferrocifens: Evidence for an Antiproliferative Effect of Hydroxyferrocifens on both Hormone-Dependent and Hormone-Independent Breast Cancer Cell Lines| journal=Chemistry, a European Journal| date=2003| volume=9| pages=5223–36 | pmid=14613131 | doi=10.1002/chem.200305024}}</ref>

===Materials chemistry===
Ferrocene, being readily sublimed, can be used to deposit certain kinds of fullerenes, especially carbon nanotubes. Due to the fact that many organic reactions can be used to modify ferrocenes, it is the case that [[vinyl]] ferrocene can be made. The vinyl ferrocene can be made by a [[Wittig reaction]] of the [[aldehyde]], a [[phosphonium salt]] and [[sodium hydroxide]].<ref>Liu, Wan-yi; Xu, Qi-hai; Ma, Yong-xiang; Liang, Yong-min; Dong, Ning-li; Guan, De-peng,''J. Organomet. Chem.'', 2001, '''625''', 128 - 132</ref> The vinyl ferrocene can be converted into a polymer which can be thought of as a ferrocenyl version of [[polystyrene]] (the phenyl groups are replaced with ferrocenyl groups).

Ferrocene is also used as a nano-sized "loom" in the manufacture of ultra-high molecular weight polyethylene's very long fibers, which are used to manufacture newer types of bulletproof vest fabric.{{Fact|date=March 2008}}

===As a ligand scaffold===
Chiral ferrocenyl [[phosphine]]s are employed as ligands for transition-metal catalyzed reactions. Some of them have found industrial applications in the synthesis of pharmaceuticals and agrochemicals.  For example, the [[diphosphine]] [[1,1'-bis(diphenylphosphino)ferrocene]] (dppf) is a valuable ligand for [[palladium]]-[[coupling reaction]]s.

==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>B.R. Waldbaum and R.C. Kerber, ''Inorg. Chim. Acta'', 1999, '''291''', 109 - 126.</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>J. Zakrzewski and C. Gianotti, ''J. Organomet. Chem.'', 1990, '''388''',175 - 180.</ref>. This compound on boiling under [[reflux]] in [[benzene]] is converted to ferrocene.<ref>A. Efraty, N. Jubran and A. Goldman, ''Inorg. Chem.'', 1982, '''21''', 868 - 873.</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= 1794–1799|date=2006| doi=10.1002/anie.200504047}}</ref>, features a cyclopentadiene derivatised with five ferrocene substituents.

[[Image:Penta(ferrocenyl)cyclopentadienyl.png|500px|center|Penta(ferrocenyl)cyclopentadienyl ligand]]

[[Image:Hexaferrocenylbenzene-3D-sticks.png|200px|thumb|right|Structure of hexaferrocenylbenzene]]

In '''hexaferrocenylbenzene''', all six positions on a [[benzene]] molecule have ferrocenyl substituents ('''R''') <ref>{{cite journal|title=Hexaferrocenylbenzene|author= Yong Yu, Andrew D. Bond, Philip W. Leonard, Ulrich J. Lorenz, Tatiana V. Timofeeva, K. Peter C. Vollhardt, Glenn D. Whitener and Andrey A. Yakovenko| journal=[[Chemical Communications]]| date=2006| pages= 2572–2574 |doi=10.1039/b604844g}}</ref>. [[X-ray diffraction]] analysis of this compound confirms that the cyclopentadienyl ligands are not co-planar with the benzene core but have alternating [[dihedral angle]]s of +30° and −80°. Due to steric crowding the ferrocenyls are slightly bent with angles of 177° and have elongated C-Fe bonds. The quaternary cyclopentadienyl carbon atoms are also [[pyramidalization|pyramidalized]]. <ref>Also, the benzene core has a [[chair conformation]] with dihedral angles of 14° and displays [[bond length]] alternation between 142.7 [[picometer|pm]] and 141.1 pm, both indications of steric crowding of the substituents.</ref>

<br clear = all/>

==References==
{{reflist|2}}

{{commonscat|ferrocene}}

==Further reading==
;Announcement of the discovery of ferrocene, but with wrong structure
*{{cite journal|author=Kealy, T. J., Pauson, P. L.|title=A New Type of Organo-iron Compound|journal= [[Nature (journal)|Nature]]| date= 1951 | volume= 168| pages =1039–40 | doi = 10.1038/1681039b0}}
* {{cite journal| author=Miller, S. A., Tebboth, J. A., Tremaine, J. F.|journal= [[Journal of the Chemical Society]] | date=1952| pages= 632–635| title=114. Dicyclopentadienyliron |doi=10.1039/JR9520000632}}
;Announcement of the correct 'sandwich' structure
*{{cite journal|author=[[Geoffrey Wilkinson|Wilkinson, G.]], Rosenblum, M., Whiting, M. C., [[Robert Burns Woodward|Woodward, R. B.]]|title= The Structure of Iron Bis-Cyclopentadienyl| journal=[[Journal of the American Chemical Society]]|date= 1952| volume=74|pages=2125–2126 | doi = 10.1021/ja01128a527}}
*{{cite journal |author=Fischer, E. O., Pfab, W.|title=Cyclopentadien-Metallkomplexe, ein neuer typ metallorganischer Verbindungen |journal=[[Zeitschrift für Naturforschung B]]|date=1952| volume=7 |pages=377–379}}
;Others
*{{cite journal|author=Dunitz, J. D., Orgel, L. E.|title=Bis-Cyclopentadienyl - A Molecular Sandwich|journal= [[Nature (journal)|Nature]] |date=1953| volume=171 |pages= 121–122 | doi = 10.1038/171121a0}}
*{{cite journal|author=Pauson, P. L.|title=Ferrocene-how it all began|journal=[[Journal of Organometallic Chemistry]]|date=2001|pages=637–639 | volume = 637-639 | doi = 10.1016/S0022-328X(01)01126-3}}
*{{cite book|author= Gerard Jaouen (ed.)| title=Bioorganometallics: Biomolecules, Labeling, Medicine| publisher=Wiley-VCH| location= Weinheim| year= 2006 | isbn=978-3-527-30990-0}} (discussion of biological role of ferrocene and related compounds)

[[Category:Iron compounds]]
[[Category:Metallocenes]]
[[Category:Antiknock agents]]

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