Potassium bis(trimethylsilyl)amide

Potassium bis(trimethylsilyl)amide (commonly abbreviated as KHMDS, Potassium(K) HexaMethylDiSilazide) or potassium hexamethyldisilazane[1] 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).

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 1,1,1-trimethyl-N-(trimethylsilyl)silanaminide
Other names
Potassium hexamethyldisilazide Potassium hexamethylsilazane[1]
Identifiers
3D model (JSmol)
Abbreviations KHMDS
ChemSpider
ECHA InfoCard 100.102.263
UN number 3263
  • InChI=1S/C6H18NSi2.K/c1-8(2,3)7-9(4,5)6;/h1-6H3;/q-1;+1 ☒N
    Key: IUBQJLUDMLPAGT-UHFFFAOYSA-N ☒N
  • C[Si](C)(C)N([K])[Si](C)(C)C
Properties
KSi
2C
6NH
18
Molar mass 199.4831 g mol−1
Appearance White, opaque crystals
Reacts
Hazards
GHS labelling:
GHS05: Corrosive
Danger
H314[2]
P280, P305+P351+P338, P310[2]
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).
☒N verify (what is checkY☒N ?)
Infobox references

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.[3]

See also

References
  1. "Potassium Hexamethyldisilazane". sigmaaldrich.com. Retrieved 1 April 2023.
  2. Potassium bis(trimethylsilyl)amide, Sigma-Aldrich
  3. 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.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.