| Revision as of 12:27, 12 May 2011 editLamro (talk | contribs)Autopatrolled, Extended confirmed users84,272 edits {{Osmium compounds}}← Previous edit |
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{{Chembox |
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| ImageFile = Osmocene.svg |
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| verifiedrevid = 428743038 |
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| ImageSize = 100px |
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| ImageFile = Osmocene_Eclipsed_Conformer_Structural_Formula.svg |
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| IUPACName = |
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| PIN = |
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| PIN = Osmocene<ref>{{cite book |author=] |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=] |pages=1041 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}</ref> |
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| OtherNames = |
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| OtherNames = {{ubl|Di(cyclopentadienyl)osmium|Bis(η<sup>5</sup>-cyclopentadienyl)osmium}} |
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|Section1={{Chembox Identifiers |
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| CASNo =1273-81-0 |
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| CASNo =1273-81-0 |
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| CASNo_Ref = {{cascite}} |
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| CASNo_Ref = {{cascite|correct|??}} |
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| SMILES = }} |
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| PubChem = 6432038 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| Section2 = {{Chembox Properties |
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| ChemSpiderID = 71493 |
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| C = 10 | H = 10 | Os = 1 |
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| SMILES = 1cccc1.1cccc1. |
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| Appearance = |
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| InChI = 1/2C5H5.Os/c2*1-2-4-5-3-1;/h2*1-5H;/q2*-1;+2 |
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| Density = |
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| InChIKey = RMYKEUKAFJLONI-UHFFFAOYAC |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| BoilingPt = |
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| StdInChI = 1S/2C5H5.Os/c2*1-2-4-5-3-1;/h2*1-5H;/q2*-1;+2 |
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| Solubility = }} |
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| Section3 = {{Chembox Hazards |
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| StdInChIKey = RMYKEUKAFJLONI-UHFFFAOYSA-N }} |
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| C=10 | H=10 | Os=1 |
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| Appearance = white solid |
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| MeltingPt = 234 °C |
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| BoilingPt = 298 °C |
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|Section3={{Chembox Structure |
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| Structure_ref = <ref name="structure"/> |
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| CrystalStruct = orthorhombic |
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| PointGroup = D<sub>5h</sub> |
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| SpaceGroup = Pnma, No. 62 |
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| OtherCompounds = ], ] |
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'''Osmocene''' is an ] found as a white solid. It is a ]. |
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'''Osmocene''' is an ] found as a white solid. It is a ] with the formula Os(C<sub>5</sub>H<sub>5</sub>)<sub>2</sub>. |
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== Synthesis == |
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Osmocene is commercially available. It may be prepared by the reaction of ] with ], followed by ] and ].<ref>{{cite journal | last1 = Bobyens | first1 = J. C. A. | last2 = Levendis | first2 = D. C. | last3 = Bruce | first3 = Michael I. | last4 = Williams | first4 = Michael L. | title = Crystal structure of osmocene, Os(η-C<sub>5</sub>H<sub>5</sub>)<sub>2</sub> | journal = Journal of Crystallographic and Spectroscopic Research | volume = 16 | pages = 519 | year = 1986 | doi = 10.1007/BF01161040}}</ref> |
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Osmocene is commercially available. It may be prepared by the reaction of ] with ] followed by ] and ].<ref name="structure">{{cite journal | last1 = Bobyens | first1 = J. C. A. | last2 = Levendis | first2 = D. C. | last3 = Bruce | first3 = Michael I. | last4 = Williams | first4 = Michael L. | title = Crystal structure of osmocene, Os(η-C<sub>5</sub>H<sub>5</sub>)<sub>2</sub> | journal = Journal of Crystallographic and Spectroscopic Research | volume = 16 | pages = 519 | year = 1986 | doi = 10.1007/BF01161040 | issue = 4| s2cid = 96874978 }}</ref> |
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It was first synthesized by ] and Heinrich Grumbert via the reaction of ] with excess ] in ], where osmium(II) chloride is presumed to be an intermediate formed ''in situ''. Alternatively, ] could be reacted with osmium(IV) chloride, though this has worse yields.<ref>{{cite journal|last1=Fischer|first1=Ernst Otto|last2=Grumbert|first2=Heinrich|title=Über Aromatenkomplexe von Metallen, XXIX. Di-cyclopentadienyl-osmium|journal=]|volume=92|issue=9|date=1959|pages=2302–2309|doi=10.1002/cber.19590920948}}</ref> |
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== Properties == |
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Osmocene is a white solid. The molecular structure features an osmium ion sandwiched between two ] rings. It is isomorphous to the lighter homologue ], both crystallizing in an eclipsed conformation. This is in contrast to ], which crystallizes with its rings staggered.<ref name="structure"/> |
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Compared to ferrocene and ruthenocene, osmocene is less reactive towards electrophilic aromatic substitution but has the greatest tendency towards ] formation with ]s.<ref>{{cite journal|last1=Kur|first1=Sally A.|last2=Rheingold|first2=Arnold L.|last3=Winter|first3=Charles H.|title=Synthesis, Characterization, and Halogenation of Decakis( acetoxymercurio)osmoene. Crystal and Molecular Structure of Decachloroosmocene|journal=]|date=1995 |volume=34|issue=1|pages=414–416|doi=10.1021/ic00105a067}}</ref> |
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The osmocenium cation <sup>+</sup> dimerizes, forming a binuclear complex with an Os-Os bond.<ref>{{cite journal|last1=Droege|first1=Michael W.|last2=Harman|first2=W. Dean|last3=Taube|first3=Henry|authorlink3=Henry Taube|title=Higher Oxidation State Chemistry of Osmocene: Dimeric Nature of the Osmocenium Ion|journal=]|date=1987 |volume=26|issue=8|pages=1309–1315|doi=10.1021/ic00255a023}}</ref> In contrast, the decamethylosmocenium cation <sup>+</sup> is stable as the monomer.<ref>{{cite book|last=Astruc|first=Didier|authorlink = Didier Astruc|title=Organometallic Chemistry and Catalysis|chapter=Metallocenes and Sandwich Complexes|page=263|publisher=Springer-Verlag|date=2007|isbn=978-3-540-46128-9|doi=10.1007/978-3-540-46129-6_13}}</ref> |
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==Uses== |
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In 2009, Horst Kunkely and Arnd Vogler reported the possibility of ] with osmocene as a catalyst.<ref>{{cite journal|last1=Kunkely|first1=Horst|last2=Vogler|first2=Arnd|title=Water Splitting by Light with Osmocene as Photocatalyst|journal=]|volume=48|issue=9|pages=1685–1687|date=2009|doi=10.1002/anie.200804712|pmid=19173275 |doi-access=free}}</ref> |
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==References== |
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==References== |
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{{Osmium compounds}} |
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{{Osmium compounds}} |
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{{Cyclopentadienide complexes}} |
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