Jump to content

Lithium cyclopentadienide

From Wikipedia, the free encyclopedia
Lithium cyclopentadienide
Names
Other names
lithium cyclopentadienylide, cyclopentadienyllithium, LiCp
Identifiers
ECHA InfoCard 100.156.001 Edit this at Wikidata
Properties
C5H5Li
Molar mass 72.04 g·mol−1
Appearance colorless solid
Density 1.064 g/cm3
decomposition
Solubility THF, dimethoxyethane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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.

Preparation, structure and reactions

[edit]

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

C5H6 + LiC4H9 → LiC5H5 + C4H10

Because lithium cyclopentadienide is usually handled as a solution, the solvent-free solid is rarely encountered. According to X-ray crystallography, LiCp 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

[edit]

References

[edit]
  1. ^ a b Reent 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.