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Alkoxydialkylsilyl derivatives for the characterization of steroids and cannabinoids by gas chromatography and mass spectrometry
Author(s) -
Harvey D. J.
Publication year - 1980
Publication title -
biomedical mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0306-042X
DOI - 10.1002/bms.1200070703
Subject(s) - chemistry , alkoxy group , mass spectrum , mass spectrometry , alkyl , alcohol , fragmentation (computing) , ion , gas chromatography , methanol , medicinal chemistry , chromatography , organic chemistry , computer science , operating system
Alkoxydimethylsilyl ethers were prepared by the reaction of the steroid or cannabinoid with bis(diethylamino)dimethylsilane followed by an alcohol. The alcohol, and hence the alkoxy group, was varied to introduce specific retention increment shifts for the gas‐liquid chromatographic separation of compounds containing different numbers of derivatizable groups. The mass spectra of these derivatives were very similar to those of the corresponding TMS derivatives. The nature of the alkoxy group could be varied so that the derivative could be made suitable for specific detection systems. Thus, the use of 2,2,2‐trifluoroethanol introduced fluorine for electron‐capture detection and N,N ‐dimethylaminoethanol introduced nitrogen. Deuterium was introduced for mass spectrometric study by the use of [ 2 H 4 ]methanol. Changing the other alkyl groups on the silicon atom from methyl to ethyl, changed the mass spectral fragmentation to give very abundant [M – C 2 H 5 ] + ions which could be used for single ion monitoring studies. Again, in these derivatives, the nature of the alkoxy group could be changed to alter the retention time of the compound and the mass of the [M – C 2 H 5 ] + ions.