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.
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Other names
lithium cyclopentadienylide, cyclopentadienyllithium, LiCp
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Identifiers | |
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ECHA InfoCard | 100.156.001 |
PubChem CID
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CompTox Dashboard (EPA)
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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).
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Infobox references
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Lithium cyclopentadienide is commercially available as a solution in tetrahydrofuran. It is prepared by treating cyclopentadiene with butyllithium:[1]
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.