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Electron impact‐induced rearrangement of trimethylsilyl groups in long chain compounds
Author(s) -
Draffan G. H.,
Stillwell R. N.,
McCloskey James A.
Publication year - 1968
Publication title -
organic mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0030-493X
DOI - 10.1002/oms.1210010508
Subject(s) - trimethylsilyl , chemistry , fragmentation (computing) , mass spectrum , mass spectrometry , electron ionization , ion , deuterium , side chain , computational chemistry , medicinal chemistry , stereochemistry , organic chemistry , chromatography , polymer , ionization , physics , quantum mechanics , computer science , operating system
Mass spectra of trimethylsilyl (TMS) derivatives of long chain dicarboxylic acids, hydroxy acids, cyano acids, and terminal diols, dithiols and diamines have been examined. A number of fragmentation pathways involving rearrangement of partial or intact TMS groups between the termini or remote points in the chain have been determined, using deuterium and carbon‐13 labeling, and high resolution mass spectrometry. Knowledge of the occurrence of functional group migrations of this type is essential to the correct interpretation of mass spectra of TMS derivatives, which are now in wide use in mass spectrometry and gas chromatography. These data in addition provide further evidence for the general ability of remote functional groups to interact, by winding or coiling of long chains. A number of interesting doubly‐charged ions are reported, in which the charges are reported, in which the charges are located at opposite ends of long chains, and for which no singly‐charged counterparts are observed.