Lithium cyclopentadienide
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Names | |
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Other names lithium cyclopentadienylide, cyclopentadienyllithium, LiCp | |
Identifiers | |
CAS Number |
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ECHA InfoCard | 100.156.001 ![]() |
PubChem CID |
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CompTox Dashboard (EPA) |
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Properties | |
Chemical formula | C5H5Li |
Molar mass | 72.04 g·mol−1 |
Appearance | colorless solid |
Density | 1.064 g/cm3 |
Solubility in water | decomposition |
Solubility | THF, dimethoxyethane |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). ![]() ![]() ![]() Infobox references |
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
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
- Sodium cyclopentadienide
References
- ^ 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.
- ^ 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.
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- Li7La3Zr2O12
- LiMn2O4
- Li2MoO4
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- Li2SO3
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- Li[SbF6]
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- Li4SiO4
- Li2SiO3
- Li2Si2O5
- LiTaO3
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- Li2TeO4
- Li2TiO3
- Li4Ti5O12
- LiTi2(PO4)3
- LiVO3·2H2O
- Li3V2(PO4)3
- Li2WO4
- LiYF4
- LiZr2(PO4)3
- Li2ZrO3
- Hemolithin (extraterrestrial protein)
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- LiC2F6NO4S2
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- Li3C6H5O7
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- (CH3)3CLi
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- LiEt3BH
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- LiC
11H
23COO
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- Cryolithionite
- Darapiosite
- Darrellhenryite
- Elbaite
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- Fluor-liddicoatite
- Emeleusite
- Eucryptite LiAlSiO4
- Faizievite
- Hectorite
- Hsianghualite
- Jadarite LiNaSiB3O7OH
- Keatite Li(AlSi2O6)
- Kunzite
- Lavinskyite
- Lepidolite
- Lithiophilite LiMnPO4
- Lithiophosphate Li3PO4
- Manandonite
- Manganoneptunite
- Nambulite
- Neptunite
- Olympite
- Petalite LiAlSi4010
- Pezzottaite Cs(Be2Li)Al2Si6O18
- Rossmanite
- Saliotite
- Sogdianite
- Spodumene LiAl(SiO3)2
- Sugilite
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- Tourmaline
- Triphylite LiFePO4
- Zabuyelite Li2CO3
- Zektzerite
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- LixBey
- HLiHe+
- LiFHeO
- LiHe2
- (HeO)(LiF)2
- La2/3-xLi3xTiO3He
- Aluminium–lithium alloys
- Heteroatom-promoted lateral lithiation
- LB buffer
- Lithium atom
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- LiNixCoyAlzO2
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- Lithium soap
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- NASICON
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