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Lithium cyclopentadienide

From Wikipedia, the free encyclopedia
Lithium cyclopentadienide
Names
Other names
lithium cyclopentadienylide, cyclopentadienyllithium, LiCp
Identifiers
3D model (JSmol)
ECHA InfoCard100.156.001Edit this at Wikidata
EC Number
  • 627-659-2
  • InChI=1S/C5H5.Li/c1-2-4-5-3-1;/h1-3H,4H2;/q-1;+1
    Key: CSOHRTAOCDVTQU-UHFFFAOYSA-N
  • [Li+].C1C=CC=[C-]1
Properties
C5H5Li
Molar mass72.04 g·mol−1
Appearancecolorless solid
Density1.064 g/cm3
decomposition
SolubilityTHF,dimethoxyethane
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound

Lithium cyclopentadienide is anorganolithium compound with theformula C5H5Li. The compound is often abbreviated as LiCp, where Cp is the cyclopentadienide anion. Lithium cyclopentadienide is a colorless solid, although samples often are pink owing to traces of oxidized impurities.

Preparation, structure and reactions

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Lithium cyclopentadienide is commercially available as a solution intetrahydrofuran. It is prepared by treatingcyclopentadiene withbutyllithium:[1]

C5H6 + LiC4H9 → LiC5H5 + C4H10

Because lithium cyclopentadienide is usually handled as a solution, the solvent-free solid is rarely encountered. According toX-ray crystallography, LiCp is a "polydecker"sandwich complex, consisting of an infinite chain of alternating Li+ centers sandwiched betweenμ-η5:η5-C5H5 ligands.[2] In the presence of amines or ethers, LiCp gives adducts, e.g. (η5-Cp)Li(TMEDA).[1] LiCp is a common reagent for the preparation ofcyclopentadienyl complexes.

See also

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References

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  1. ^abReent Michel; Regine Herbst-Irmer; Dietmar Stalke (2011)."Revealing Coordination Patterns in C5-Cyclic Lithium Organics".Organometallics.30 (16):4379–4386.doi:10.1021/om200471e.
  2. ^Robert E. Dinnebier; Ulrich Behrens & Falk Olbrich (1997). "Solid State Structures of Cyclopentadienyllithium, -sodium, and -potassium. Determination by High-Resolution Powder Diffraction".Organometallics.16 (17):3855–3858.doi:10.1021/om9700122.
Inorganic (list)
Organic (soaps)
Minerals
Hypothetical
Other Li-related
Salts and covalent derivatives of thecyclopentadienide ion
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