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The problem of the azatropylium ion: Hydrogen elimination from the molecular ion of γ‐picoline
Author(s) -
Neeter R.,
Nibbering N. M. M.,
De Boer Th. J.
Publication year - 1970
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.1210030508
Subject(s) - picoline , deuterium , ion , chemistry , hydrogen , polyatomic ion , ring (chemistry) , hydrogen isotope , methyl group , isotope , kinetic isotope effect , hydrogen molecule , medicinal chemistry , group (periodic table) , organic chemistry , atomic physics , pyridine , physics , nuclear physics
Comparison of the mass spectrum of γ‐picoline with that of analogues, specifically deuterated in the methyl group, the ring or both, has shown that the molecular ion loses the α,β and methyl hydrogen atoms (ω‐hydrogen') in the ratio 1.43: 1: 1. 13. The same trend is found for the elimination of HCN from the molecular ion. Moreover, a value of 1.52 is found for the isotope effect, expressing the favoured loss of H over D, irrespective of its position.