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The Mass Spectrometric Fragmentation of 1‐Alkyl Ions derived from Halides
Author(s) -
Fiaux A.,
Wirz B.,
Gäumann T.
Publication year - 1974
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19740570324
Subject(s) - chemistry , fragmentation (computing) , halide , ion , hydrogen , alkyl , olefin fiber , mass spectrum , electron ionization , medicinal chemistry , stereochemistry , photochemistry , organic chemistry , catalysis , computer science , operating system , ionization
The mass‐spectrometric fragmentation of n ‐pentyl, n ‐hexyl, n ‐octyl and n ‐nonyl ions has been studied using 13 C‐ and D‐labelling. The ions were produced from the corresponding halide ions. The loss of an olefin as a neutral fragment is the main reaction. The elimination of this fragment must be by a complex mechanism, since the terminal carbon atoms have the smallest probability of being lost with the neutral fragment. On chains with five to six carbon atoms, hydrogen scrambling seems to preceed the fragmentation; this is not true for hydrogen on terminal positions of longer chains. Ring formation prior to the fragmentation could explain some of the results; but no reasonable conclusion could be reached.