*** Welcome to piglix ***

Phenyllithium

Phenyllithium
Kekulé, skeletal formula of phenyllithium
Names
Systematic IUPAC name
Phenyllithium
Other names
Phenyl lithium
Identifiers
591-51-5 YesY
3D model (Jmol) Interactive image
Abbreviations LiPh, PhLi
506502
ChEBI CHEBI:51470 N
ChemSpider 10254416 N
ECHA InfoCard 100.008.838
EC Number 209-720-1
2849
MeSH phenyllithium
PubChem 637932
Properties
LiC
6
H
5
Molar mass 84.045 g mol−1
Appearance Colorless crystals
Density 828 mg cm−3
Boiling point 140 to 143 °C (284 to 289 °F; 413 to 416 K)
Reacts
Thermochemistry
48.3-52.5 kJ mol−1
Hazards
Safety data sheet External MSDS
R-phrases R14, R17, R23/24/25, R48
S-phrases (S1/2), S8, S9, S16, S26, S30, S46, S36/37/39, S45
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
Infobox references

Phenyllithium or lithobenzene is an organometallic agent with the empirical formula C6H5Li. It is most commonly used as a metalating agent in organic syntheses and a substitute for Grignard reagents for introducing phenyl groups in organic syntheses. Crystalline phenyllithium is colorless; however, solutions of phenyllithium are various shades of brown or red depending on the solvent used and the impurities present in the solute.

Phenyllithium is an organolithium compound that forms monoclinic crystals. Solid phenyllithium can be described as consisting of dimeric Li2Ph2 subunits. The Li atoms and the ipso carbons of the phenyl rings form a planar four-membered ring. The plane of the phenyl groups are perpendicular to the plane of this Li2C2 ring. Additional strong intermolecular bonding occurs between these phenyllithium dimers and the π-electrons of the phenyl groups in the adjacent dimers, resulting in an infinite polymeric ladder structure.

Ball-and-stick model of part of a ladder in the crystal structure of unsolvated phenyllithium

In solution, it takes a variety of structures dependent on the organic solvent. In tetrahydrofuran, it equilibrates between monomer and dimer states. In ether, as it is commonly sold, phenyllithium exists as a tetramer. Four Li atoms and four ipso carbon centers occupy alternating vertices of a distorted cube. Phenyl groups are at the faces of the tetrahedron and bind to three of the nearest Li atoms.

Stick model of the crystal structure of the phenyllithium etherate tetramer - ether ethyl groups omitted for clarity


...
Wikipedia

...