Potassium bis(trimethylsilyl)amide

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Potassium bis(trimethylsilyl)amide
Stereo, skeletal formula of potassium bis(trimethylsilyl)amide dimer
Ball and stick model of potassium bis(trimethylsilyl)amide dimer
Names
Preferred IUPAC name
Potassium bis(trimethylsilyl)amide[citation needed]
Other names
Potassium hexamethyldisilazide[citation needed]
Identifiers
Abbreviations KHMDS
40949-94-8 YesY
ChemSpider 21171158 N
Jmol-3D images 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 The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
H314[1]
P280, P305+351+338, P310[1]
EU classification Corrosive 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 noted otherwise, data is 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).[citation needed]

Structure[edit]

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[edit]

References[edit]

  1. ^ a b c d e 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.