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Solution structures are either solvated monomers or dimers (or mixtures thereof) with this depending on the coordinating power, concentration, and temperature of the solvent. [3] In general, weakly coordinating solvents such as toluene and N,N-dimethylethylamine give dimers, where as THF and diglyme gave monomers at high dilution. [ 3 ]
Lithium, sodium, and potassium bis(trimethylsilyl)amides are commercially available. When free of solvent, the lithium [5] and sodium [6] complexes are trimeric, and ...
Metal amides (systematic name metal azanides) are a class of coordination compounds composed of a metal center with amide ligands of the form NR 2 −. Amido complexes of the parent amido ligand NH 2 − are rare compared to complexes with diorganylamido ligand, such as dimethylamido. Amide ligands have two electron pairs available for bonding.
Bis(trimethylsilyl)amine (also known as hexamethyldisilazane and HMDS) is an organosilicon compound with the molecular formula [(CH 3) 3 Si] 2 NH. The molecule is a derivative of ammonia with trimethylsilyl groups in place of two hydrogen atoms.
The halide acts as a leaving group and ends up in solution. A workup step follows to remove any excess base within the solution. The overall reaction scheme is as follows: ROH + NEt 3 → RO − + H−NEt + 3; RO − + Cl−SiMe 3 → RO−SiMe 3 + Cl −; Bis(trimethylsilyl)acetamide, a popular reagent for silylation
NaHMDS is used as a strong base in organic synthesis.Typical reactions: To deprotonate ketones and esters to generate enolate derivatives. [3]Generate carbenes by dehydrohalogenation of halocarbons.
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LiHMDS is often used in organic chemistry as a strong non-nucleophilic base. [3] Its conjugate acid has a pK a of ~26, [4] making it is less basic than other lithium bases, such as LDA (pK a of conjugate acid ~36).