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A novel hydrogen rearrangement of bifunctional o ‐xylylene derivatives in chemical ionization mass spectrometry
Author(s) -
Nakata Hisao,
Osogoshi Keisuke,
Noda Yasuyo,
Abe Ayako,
Suzuki Hiroshi
Publication year - 1994
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/rcm.1290080123
Subject(s) - chemistry , hydride , mass spectrometry , bifunctional , xylylene , ion , deuterium , mass spectrum , hydrogen , cationic polymerization , photochemistry , proton , reaction mechanism , chemical ionization , computational chemistry , ionization , organic chemistry , catalysis , atomic physics , physics , chromatography , quantum mechanics
A novel hydrogen rearrangement reaction was found in benzyl ions that have a (benzyl) group (Z=O or N) at their ortho position. From deuterium labeling experiments, mass analyzed ion kinetic energy spectra with collisional activation, and examination of structure‐peak intensity correlation, a mechanism is proposed which involves a direct transfer of hydrogen (hydride) to the structurally remote but spatially close cationic center. The possibility of an alternative, less likely mechanism including an ion/neutral complex and/or a proton‐bridged complex has also been discussed.