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Chain length effects in the competition between intramolecular hydrogen migrations in the molecular ions of hydrogen migration in the molecular ions of α‐benzylamino‐ω‐benzyloxyalkanes as studied by deuterium labelling
Author(s) -
Bruins Andries P.,
Nibbering Nico M. M.
Publication year - 1976
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.1210110307
Subject(s) - chemistry , deuterium , ion , intramolecular force , hydrogen , hydrogen atom , reactivity (psychology) , bifunctional , molecule , labelling , transition state , benzaldehyde , photochemistry , stereochemistry , alkyl , organic chemistry , catalysis , atomic physics , alternative medicine , pathology , medicine , biochemistry , physics
The unimolecular decompositions upon electron impact of the bifunctional compounds ØCH 2 ‐NH(CH 2 ) n ‐OCH 2 Ø(n=2 to 7)have been studied by deuterium labelling. The molecular ions lose a benzyl radical and/or a benzaldehyde molecule, depending on the length of the aliphatic chain. Both reactions appear to be the result of the transfer of a hydrogen atom to the charge localized amino function in a cyclic transition state. The ring size of this transition state turns out to play a far more important role than the difference in reactivity of the migrating hydrogen atoms.