Exploring the solid state and solution structural chemistry of the utility amide potassium hexamethyldisilazide (KHMDS)

Ojeda-Amador, Ana I. and Martínez-Martínez, Antonio J. and Robertson, Gemma M. and Robertson, Stuart D. and Kennedy, Alan R. and O'Hara, Charles T. (2017) Exploring the solid state and solution structural chemistry of the utility amide potassium hexamethyldisilazide (KHMDS). Dalton Transactions, 46 (19). pp. 6392-6403. ISSN 1477-9234 (https://doi.org/10.1039/C7DT01118K)

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Abstract

The structural chemistry of eleven donor complexes of the important Brønsted base potassium 1,1,1,3,3,3-hexamethyldisilazide (KHMDS) has been studied. Depending on the donor, each complex adopted one of four general structural motifs. Specifically, in this study the donors employed were toluene (to give polymeric 1 and dimeric 2), THF (dimeric 3), N,N,N',N'-tetramethylethylenediamine (TMEDA) (dimeric 4), (R,R)-N,N,N',N'-tetramethyl-1,2-diaminocyclohexane [(R,R)-TMCDA] (dimeric 5), 12-crown-4 (dimeric 6), N,N,N',N'-tetramethyldiaminoethyl ether (TMDAE) (tetranuclear dimeric 8 and monomeric 10), N,N,N',N',N''-pentamethyldiethylentriamine (PMDETA) (tetranuclear dimeric 7), tris[2-dimethyl(amino)ethyl]amine (Me6TREN) (tetranuclear dimeric 9) and tris{2-(2-methoxyethoxy)ethyl}amine (TMEEA) (monomeric 11). The complexes were also studied in solution by 1H and 13C NMR spectroscopy as well as DOSY NMR spectroscopy.

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