Jump to content

Lithium cyclopentadienide

From Wikipedia, the free encyclopedia

This is the current revision of this page, as edited by Graeme Bartlett (talk | contribs) at 21:28, 25 January 2025 (more ids). The present address (URL) is a permanent link to this version.

(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff)
Lithium cyclopentadienide
Names
Other names
lithium cyclopentadienylide, cyclopentadienyllithium, LiCp
Identifiers
3D model (JSmol)
ECHA InfoCard 100.156.001 Edit 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 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.