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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 ...
The lithium amides are more common and more soluble than the other alkali metal analogs. Potassium amides are prepared by transmetallation of lithium amides with potassium t-butoxide (see also Schlosser base ) or by reaction of the amine with potassium , potassium hydride , n-butylpotassium , or benzylpotassium .
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]
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.
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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