molybdocene dichloride
{{chembox
| verifiedrevid =
| ImageFileL1 = Cp2MoCl2-2D-skeletal.png
| ImageSizeL1 =
| ImageNameL1 =
| ImageFileR1 = Cp2MoCl2-from-xtal-1974-3D-balls.png
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| IUPACName = dichlorobis(η5-cyclopentadienyl)molybdenum(IV)
| OtherNames = molybdocene dichloride,
molybdenocene dichloride,
dichloridobis(cyclopentadienyl)molybdenum(IV)
|Section1={{Chembox Identifiers
| CASNo_Ref =
| CASNo = 12184-22-4
| RTECS =
| PubChem = 452153
| ChemSpiderID = 398274
| SMILES = [cH-]1cccc1.[cH-]1cccc1.Cl[Mo+2]Cl
| InChI = 1/2C5H5.2ClH.Mo/c2*1-2-4-5-3-1;;;/h2*1-5H;2*1H;/q2*-1;;;+2/p-2/r2C5H5.Cl2Mo/c2*1-2-4-5-3-1;1-3-2/h2*1-5H;/q2*-1;
| InChIKey = QGGWSCVAFKWITK-OWLYHJECAX
| StdInChI = 1S/2C5H5.2ClH.Mo/c2*1-2-4-5-3-1;;;/h2*1-5H;2*1H;/q2*-1;;;+2/p-2
| StdInChIKey = QGGWSCVAFKWITK-UHFFFAOYSA-L
}}
|Section2={{Chembox Properties
| Formula = C10H10Cl2Mo
| MolarMass = 297.04 g·mol−1
| Appearance = greenish-brown powder
| Density =
| Solubility = insoluble, moisture sensitive
| MeltingPt = }}
|Section3={{Chembox Structure
| Coordination =
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|Section7={{Chembox Hazards
| ExternalSDS = {{cite web|title = 42-0100 Molybdenum " Bis(cyclopentadienyl)molybdenum dichloride, 99%|url = http://www.strem.com/catalog/v/42-0100/43/molybdenum_12184-22-4|publisher = Strem Chemicals|access-date = 5 February 2012|date = 27 July 2011}}
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|Section8={{Chembox Related
| OtherCompounds = Ferrocene
Zirconocene dichloride
Vanadocene dichloride
Niobocene dichloride
Titanocene dichloride
Tantalocene dichloride}}
}}
Molybdocene dichloride is the organomolybdenum compound with the formula (η5-C5H5)2MoCl2 and IUPAC name dichlorobis(η5-cyclopentadienyl)molybdenum(IV), and is commonly abbreviated as Cp2MoCl2. It is a brownish-green air- and moisture-sensitive powder. In the research laboratory, it is used to prepare many derivatives.
Preparation and structure
The compound is prepared from molybdocene dihydride by treatment with chloroform:{{cite book | last1 = Silavwe | first1 = Ned D. | title = Inorganic Syntheses | last2 = Castellani | first2 = Michael P. | last3 = Tyler | first3 = David R. | year = 1992 | chapter = Bis(η5-Cyclopentadienyl)Molybdenum(IV) Complexes | volume = 29 | pages = 204–211 | doi = 10.1002/9780470132609.ch50 | isbn = 9780470132609 }}
:(C5H5)2MoH2 + 2 CHCl3 → (C5H5)2MoCl2 + 2 CH2Cl2
The compound adopts a "clamshell" structure where the Cp rings are not parallel, the average Cp(centroid)-M-Cp angle being 130.6°. The two chloride ligands are cis, the Cl-Mo-Cl angle of 82° being narrower than in niobocene dichloride (85.6°), which in turn is less than in zirconacene dichloride (92.1°). This trend helped to establish the orientation of the HOMO in this class of complex.K. Prout, T. S. Cameron, R. A. Forder, and in parts S. R. Critchley, B. Denton and G. V. Rees "The crystal and molecular structures of bent bis-π{{nbh}}cyclopentadienyl-metal complexes: (a) bis-π{{nbh}}cyclopentadienyldibromorhenium(V) tetrafluoroborate, (b) bis-π{{nbh}}cyclopentadienyldichloromolybdenum(IV), (c) bis-π{{nbh}}cyclopentadienylhydroxomethylaminomolybdenum(IV) hexafluorophosphate, (d) bis-π{{nbh}}cyclopentadienylethylchloromolybdenum(IV), (e) bis-π{{nbh}}cyclopentadienyldichloroniobium(IV), (f) bis-π{{nbh}}cyclopentadienyldichloromolybdenum(V) tetrafluoroborate, (g) μ{{nbh}}oxo-bis[bis-π{{nbh}}cyclopentadienylchloroniobium(IV)] tetrafluoroborate, (h) bis-π{{nbh}}cyclopentadienyldichlorozirconium" Acta Crystallogr. 1974, volume B30, pp. 2290–2304. {{doi|10.1107/S0567740874007011}}
Uses
Unlike the titanocene and zirconacene derivatives, the molybdocene compounds have yielded no commercial applications.
All metallocene dihalides exhibit some anti-cancer activity,{{cite book|title = Bioinorganic Chemistry: A Short Course|first = R. M.|last = Roat-Malone|edition = 2nd|year = 2007|publisher = John Wiley & Sons|pages = 19–20|isbn = 978-0-471-76113-6|url = https://books.google.com/books?id=Ykx54y7LdK8C&q=molybdocene+dichloride&pg=PA20}} but these have not yielded useful compounds in the clinic.{{cite journal|title = Organometallic Anticancer Agents: Cellular Uptake and Cytotoxicity Studies on Thiol Derivatives of the Antitumor Agent Molybdocene Dichloride|author1 = Waern, J. B.|author2 = Dillon, C. T.|author3 = Harding, M. M.|journal = J. Med. Chem.|year = 2005|volume = 48|issue = 6|pages = 2093–2099|doi = 10.1021/jm049585o|pmid = 15771451}}
References
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{{Cyclopentadienide complexes}}
{{Commons category|Molybdocene dichloride}}
{{DEFAULTSORT:Molybdocene Dichloride}}
Category:Organomolybdenum compounds