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Molybdocene dichloride

Molybdocene dichloride
Names
IUPAC name
dichlorobis(η5-cyclopentadienyl)molybdenum(IV)
Other names
molybdocene dichloride,
molybdenocene dichloride,
dichloridobis(cyclopentadienyl)molybdenum(IV)
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.159.644 Edit this at Wikidata
  • InChI=1S/2C5H5.2ClH.Mo/c2*1-2-4-5-3-1;;;/h2*1-5H;2*1H;/q2*-1;;;+2/p-2
    Key: QGGWSCVAFKWITK-UHFFFAOYSA-L
  • 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;
    Key: QGGWSCVAFKWITK-OWLYHJECAX
  • [cH-]1cccc1.[cH-]1cccc1.Cl[Mo+2]Cl
Properties
C10H10Cl2Mo
Molar mass 297.04 g·mol−1
Appearance greenish-brown powder
insoluble, moisture sensitive
Hazards
Safety data sheet (SDS) [1]
Related compounds
Related compounds
 Ferrocene
Zirconocene dichloride
Vanadocene dichloride
Niobocene dichloride
Titanocene dichloride
Tantalocene dichloride
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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:[2]

(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.[3]

Uses

Unlike the titanocene and zirconacene derivatives, the molybdocene compounds have yielded no commercial applications.

All metallocene dihalides exhibit some anti-cancer activity,[4] but these have not yielded useful compounds in the clinic.[5]

References

  1. ^ "42-0100 Molybdenum " Bis(cyclopentadienyl)molybdenum dichloride, 99%". Strem Chemicals. 27 July 2011. Retrieved 5 February 2012.
  2. ^ Silavwe, Ned D.; Castellani, Michael P.; Tyler, David R. (1992). "Bis(η5-Cyclopentadienyl)Molybdenum(IV) Complexes". Inorganic Syntheses. Vol. 29. pp. 204–211. doi:10.1002/9780470132609.ch50. ISBN 9780470132609.
  3. ^ 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-cyclopentadienyl-metal complexes: (a) bis-π-cyclopentadienyldibromorhenium(V) tetrafluoroborate, (b) bis-π-cyclopentadienyldichloromolybdenum(IV), (c) bis-π-cyclopentadienylhydroxomethylaminomolybdenum(IV) hexafluorophosphate, (d) bis-π-cyclopentadienylethylchloromolybdenum(IV), (e) bis-π-cyclopentadienyldichloroniobium(IV), (f) bis-π-cyclopentadienyldichloromolybdenum(V) tetrafluoroborate, (g) μ-oxo-bis[bis-π-cyclopentadienylchloroniobium(IV)] tetrafluoroborate, (h) bis-π-cyclopentadienyldichlorozirconium" Acta Crystallogr. 1974, volume B30, pp. 2290–2304. doi:10.1107/S0567740874007011
  4. ^ Roat-Malone, R. M. (2007). Bioinorganic Chemistry: A Short Course (2nd ed.). John Wiley & Sons. pp. 19–20. ISBN 978-0-471-76113-6.
  5. ^ Waern, J. B.; Dillon, C. T.; Harding, M. M. (2005). "Organometallic Anticancer Agents: Cellular Uptake and Cytotoxicity Studies on Thiol Derivatives of the Antitumor Agent Molybdocene Dichloride". J. Med. Chem. 48 (6): 2093–2099. doi:10.1021/jm049585o. PMID 15771451.
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