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Mass spectrometry of aralkyl compounds with a functional group—IX: Hydrogen scrambling in the molecular ion of hydrocinnamaldehyde
Author(s) -
Venema A.,
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.1210030507
Subject(s) - chemistry , hydrogen atom , polyatomic ion , deuterium , hydrogen , mass spectrum , ring (chemistry) , ion , mass spectrometry , scrambling , group (periodic table) , medicinal chemistry , crystallography , stereochemistry , organic chemistry , linguistics , physics , philosophy , chromatography , quantum mechanics
Abstract The molecular ion of hydrocinnamaldehyde (C 6 H 5 CH 2 CH 2 CHO) chiefly loses fragments C 2 H 2 O and C 3 H 4 O. Mass spectra of specifically deuterated analogues show that in the loss of C 2 H 2 O an α‐hydrogen atom (with respect to the aldehyde group) is transferred to the aromatic part. A shift of the aldehydic hydrogen to one of the ortho positions of the phenyl ring and loss of C 2 H 2 O by a McLafferty rearrangement is not observed. In the loss of C 3 H 4 O also an α‐hydrogen atom migrates to the aromatic part. Both reactions appear to occur with an extensive randomization of all hydrogen atoms in the molecular ion.