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Mass spectrometry of hydroxy dicarboxylic acids as trimethylsilyl derivatives. Rearrangement fragmentations.

Göran Petersson (Institutionen för teknisk kemi)
Organic Mass Spectrometry Vol. 6 (1972), p. 565-576.
[Artikel, refereegranskad vetenskaplig]

Gas chromatography - mass spectrometry offers a convenient method for the separation and identification of hydroxy dicarboxylic acids as open-chain trimethylsilyl (TMS) derivatives. Mass spectra were studied of aldaric (tartronic, tartaric, pentaric and hexaric) acids and deoxyaldaric (malic, 2-deoxypentaric, 2-deoxyhexaric, 3-deoxypentaric and 3-deoxyhexaric) acids. The different structural types can be readily identified from their characteristic spectra.

The most prominent fragmentations involving the rupture of one bond are the loss of a siliconlinked methyl group and the formation of alfa-cleavage ions by carbon chain cleavage. The further decay is characterized by a number of significant rearrangements specific of TMS derivatives. Several of these can be classified as involving migration of a TMS group to an oxygen atom or migration of an ester OTMS group to a silicon atom. Concomitant loss of a stable molecule often provides a driving force.

Prominent odd-electron ions are formed by a McLafferty-type rearrangement of a TMS group. The decomposition of several even-electron ions can be regarded as analogous to that rearrangement.

Denna post skapades 2010-01-30. Senast ändrad 2011-06-08.
CPL Pubid: 111262


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