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Hydrogen Rearrangements in the Mass Spectra of Alkylbenzenes

Volume 25, Number 2 (April 1971) Page 253-258

Lightner, David A.; Quistad, Gary B.; Irwin, Elizabeth


By means of extensive deuterium labeling, the γ-carbon has been shown to be the principal site of transferred hydrogen (deuterium) regardless whether the hydrogen (deuterium) is primary, secondary, or tertiary. Although a significant transfer is also observed from the β, δ, ɛ, and more remote (to θ) carbons of the alkyl chain, such transfer is not attended by C-C cleavage (fragmentation) and is interpreted as an exchange between the aromatic ring (ortho-hydrogen atoms) and the alkyl chain hydrogen atoms (deuterium atoms). The data herein also set small upper limits on the formation of m/e 91 (C7H7+) from m/e 92 (C7H8+.) at both high and low ionizing voltages as well as in long and short alkyl chains.