Potassium bis(trimethylsilyl)amide: Difference between revisions
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|ImageFile = KHMDS.png |
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| ImageFile = KHMDS.png |
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|ImageName = Stereo, skeletal formula of potassium bis(trimethylsilyl)amide dimer |
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|ImageFile2 = Potassium bis(trimethylsilyl)amide unsolvated from crystal.png |
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| OtherNames = Potassium hexamethyldisilazane |
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| Section1 = {{Chembox Identifiers |
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|ImageName2 = Ball and stick model of potassium bis(trimethylsilyl)amide dimer |
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| Abbreviations = KHMDS |
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|PIN = Potassium 1,1,1-trimethyl-''N''-(trimethylsilyl)silanaminide |
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| CASNo = 40949-94-8 |
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|OtherNames = Potassium hexamethyldisilazide |
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| EINECS = |
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Potassium hexamethylsilazane<ref name=auto>{{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 |
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|website=sigmaaldrich.com|title=Potassium Hexamethyldisilazane}}</ref> |
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|Abbreviations = KHMDS |
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|CASNo = 40949-94-8 |
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|PubChem = 3251421 |
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|UNNumber = 3263 |
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|SMILES = C[Si](C)(C)N([K])[Si](C)(C)C |
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|StdInChI = 1S/C6H18NSi2.K/c1-8(2,3)7-9(4,5)6;/h1-6H3;/q-1;+1 |
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| C = 6 | H = 18 | K = 1 | N = 1 | Si = 2 |
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|StdInChIKey = IUBQJLUDMLPAGT-UHFFFAOYSA-N |
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|Formula = {{Chem|KSi|2|C|6|NH|18}} |
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| OtherCations = [[Lithium bis(trimethylsilyl)amide]], [[Sodium bis(trimethylsilyl)amide]] |
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|MolarMass = 199.4831 g mol<sup>−1</sup> |
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|Appearance = White, opaque crystals |
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|Solubility = Reacts |
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|GHSPictograms = {{GHS corrosion}} |
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|GHSSignalWord = '''DANGER''' |
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|HPhrases = {{H-phrases|314}}<ref name=sigmaaldrich>[http://www.sigmaaldrich.com/catalog/product/aldrich/324671?lang=en Potassium bis(trimethylsilyl)amide], [[Sigma-Aldrich]]</ref> |
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|PPhrases = {{P-phrases|280|305+351+338|310}}<ref name=sigmaaldrich/> |
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|Section4={{Chembox Related |
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|OtherCations = [[Lithium bis(trimethylsilyl)amide]]<br /> |
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[[Sodium bis(trimethylsilyl)amide]] |
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'''Potassium bis(trimethylsilyl)amide''' (commonly abbreviated as '''KHMDS''', Potassium('''K''') '''H'''exa'''M'''ethyl'''D'''i'''S'''ilazide) or potassium hexamethyldisilazane<ref name="auto"/> is the chemical compound with the formula ((CH<sub>3</sub>)<sub>3</sub>Si)<sub>2</sub>NK. It is a strong, non-nucleophilic base with an approximate pK<sub>a</sub> of 26 (compare to [[lithium diisopropylamide]], at 36).{{Citation needed|date = September 2011}} |
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==Structure== |
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'''Potassium bis(trimethylsilyl)amide''' is the chemical compound with the formula ((CH<sub>3</sub>)<sub>3</sub>Si)<sub>2</sub>NK. This species is usually called potassium hexamethyldisilazane (KHMDS), although the proper nomenclature is potassium hexamethyldisilazanide since the nitrogen is deprotonated. It is a strong, non-nucleophilic base with an approximate pK<sub>a</sub> of 26 (compare to [[lithium diisopropylamide]], at 36). |
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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 pair]]ing.<ref>{{cite journal | doi = 10.1021/ic00333a029 | journal = [[Inorg. Chem.]] | title = Ion pairing in [bis(trimethylsilyl)amido]potassium: The x-ray crystal structure of unsolvated [KN(SiMe3)2]2 | year = 1990 | last1 = Tesh | first1 = Kris F. | last2 = Hanusa | first2 = Timothy P. | last3 = Huffman | first3 = John C. | volume = 29 | issue = 8 | pages = 1584–1586}}</ref> |
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==See also== |
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[[Category:Reagents for organic chemistry]] |
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* [[Metal bis(trimethylsilyl)amides]] |
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[[Category:organosilicon compounds]] |
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==References== |
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{{organic-compound-stub}} |
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<references/> |
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[[Category:Bis(trimethylsilyl)amides]] |
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[[de:Kaliumhexamethyldisilizan]] |
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[[Category:Potassium compounds]] |
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[[Category:Non-nucleophilic bases]] |
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