Lithium cyclopentadienide

Lithium cyclopentadienide is an organolithium compound with the formula 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.

Lithium cyclopentadienide
Names
Other names
lithium cyclopentadienylide, cyclopentadienyllithium, LiCp
Identifiers
ECHA InfoCard 100.156.001
Properties
C5H5Li
Molar mass 72.04 g·mol−1
Appearance colorless solid
Density 1.064 g/cm3
decomposition
Solubility THF, dimethoxyethane
Hazards
Main hazards flammable
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Preparation, structure and reactions

Lithium cyclopentadienide is commercially available as a solution in THF. It is prepared by treating cyclopentadiene with butyllithium:[1]

C5H6 + LiC4H9 → LiC5H5 + C4H10

Crystalline solvent-free LiCp, which is rarely encountered, is a "polydecker" sandwich complex, consisting of an infinite chain of alternating Li+ centers sandwiched between μ-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 of cyclopentadienyl complexes.

See also

References
  1. Reent Michel, Regine Herbst-Irmer, Dietmar Stalke (2011). "Revealing Coordination Patterns in C5-Cyclic Lithium Organics". Organometallics. 30: 4379–4386. doi:10.1021/om200471e.CS1 maint: uses authors parameter (link)
  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: 3855–3858. doi:10.1021/om9700122.
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