Potassium bis(trimethylsilyl)amide

Potassium bis(trimethylsilyl)amide
Names
Preferred IUPAC name
Potassium bis(trimethylsilyl)amide
Other names
Potassium hexamethyldisilazide
Identifiers
40949-94-8 YesY
Abbreviations KHMDS
ChemSpider 21171158 N
Jmol interactive 3D Image
PubChem 3251421
UN number 3263
Properties
KSi
2
C
6
NH
18
Molar mass 199.4831 g mol−1
Appearance White, opaque crystals
Reacts
Hazards
GHS pictograms
GHS signal word DANGER
H314[1]
P280, P305+351+338, P310[1]
C[1]
R-phrases R14, R34[1]
S-phrases S26, S36/37/39, S43, S45[1]
Related compounds
Other cations
Lithium bis(trimethylsilyl)amide

Sodium bis(trimethylsilyl)amide

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Potassium bis(trimethylsilyl)amide (commonly abbreviated as KHMDS, Potassium(K) HexaMethylDiSilazide) 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

In the solid state, the unsolvated compound is dimeric, with two potassium and two nitrogen atoms forming a square. This compound is soluble in hydrocarbon solvents, and conducts electricity poorly in solution and in the melt. This is attributed to very strong ion-pairing.[2]

See also

References

  1. 1 2 3 4 5 Potassium bis(trimethylsilyl)amide, Sigma-Aldrich
  2. Tesh, Kris F.; Hanusa, Timothy P.; Huffman, John C. (1990). "Ion pairing in [bis(trimethylsilyl)amido]potassium: The x-ray crystal structure of unsolvated [KN(SiMe3)2]2". Inorg. Chem. 29 (8): 1584–1586. doi:10.1021/ic00333a029.


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