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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).
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.
The structures of common lithium amides, such as lithium diisopropylamide (LDA) and lithium hexamethyldisilazide (LiHMDS) have been extensively studied by Collum and coworkers using NMR spectroscopy. [17] Another important class of reagents is silyllithiums, extensively used in the synthesis of organometallic complexes and polysilane dendrimers.
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.
Lithium tetramethylpiperidide (LiTMP or harpoon base) Other strong non-nucleophilic bases are sodium hydride and potassium hydride . These compounds are dense, salt-like materials that are insoluble and operate by surface reactions.
Lithium amide or lithium azanide is an inorganic compound with the chemical formula LiNH 2. It is a white solid with a tetragonal crystal structure. [1] Lithium amide can be made by treating lithium metal with liquid ammonia: [2] 2 Li + 2 NH 3 → 2 LiNH 2 + H 2. Lithium amide decomposes into ammonia and lithium imide upon heating. [3]
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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