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Potassium bis(trimethylsilyl)amide

Potassium hexamethylsilazane{{cite web|url=https://www.sigmaaldrich.com/ES/es/search/potassium-hexamethyldisilazane?focus=products&page=1&perpage=30&sort=relevance&term=potassium%20hexamethyldisilazane&type=product|access-date=1 April 2023

Sodium bis(trimethylsilyl)amide

Potassium bis(trimethylsilyl)amide (commonly abbreviated as KHMDS, Potassium(K) HexaMethylDiSilazide) or potassium hexamethyldisilazane is the chemical compound with the formula ((CH3)3Si)2NK. It is a strong, non-nucleophilic base with an approximate pKa of 26 (compare to lithium diisopropylamide, at 36).

Structure

The methylsilyl groups give KHMDS good solubility in most organic solvents. Solution structures are either solvated monomers or dimers (or mixtures thereof) with this depending on the coordinating power, concentration, and temperature of the solvent. In general, weakly coordinating solvents such as toluene and N,N-dimethylethylamine give dimers, where as THF and diglyme gave monomers at high dilution. In the solid state, the unsolvated compound is dimeric, with two potassium and two nitrogen atoms forming a square. KHMDS conducts electricity poorly in solution and in the melt, which is attributed to very strong ion pairing.

References

References

  1. [http://www.sigmaaldrich.com/catalog/product/aldrich/324671?lang=en Potassium bis(trimethylsilyl)amide], [[Sigma-Aldrich]]
  2. (20 June 2024). "Potassium Hexamethyldisilazide (KHMDS): Solvent-Dependent Solution Structures". Journal of the American Chemical Society.
  3. (1990). "Ion pairing in [bis(trimethylsilyl)amido]potassium: The x-ray crystal structure of unsolvated [KN(SiMe3)2]2". [[Inorg. Chem.]].
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bis(trimethylsilyl)amides potassium-compounds non-nucleophilic-bases
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