Potassium bis(trimethylsilyl)amide
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).
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| Names | |
|---|---|
| Preferred IUPAC name
Potassium 1,1,1-trimethyl-N-(trimethylsilyl)silanaminide | |
| Other names
Potassium hexamethyldisilazide | |
| Identifiers | |
3D model (JSmol) |
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| Abbreviations | KHMDS |
| ChemSpider | |
| ECHA InfoCard | 100.115.605 |
PubChem CID |
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| UN number | 3263 |
CompTox Dashboard (EPA) |
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| Properties | |
| KSi 2C 6NH 18 | |
| Molar mass | 199.4831 g mol−1 |
| Appearance | White, opaque crystals |
| Reacts | |
| Hazards | |
| GHS pictograms |  |
| GHS Signal word | Danger |
GHS hazard statements |
H314[1] |
| P280, P305+351+338, P310[1] | |
| Related compounds | |
Other cations |
Lithium 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 | |
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]
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See also
References
- Potassium bis(trimethylsilyl)amide, Sigma-Aldrich
- 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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