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2‐(1‐Azulyl)ethyl tosylate methylene scrambling in the gas phase. Similarities to solution chemistry
Author(s) -
Graham Cooks R.,
McDonald Richard N.,
Curtis James R.,
Petty Herbert E.
Publication year - 1971
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.1210050704
Subject(s) - chemistry , methylene , scrambling , ion , molecule , mass spectrometry , chemical ionization , photochemistry , medicinal chemistry , inorganic chemistry , ionization , computational chemistry , organic chemistry , chromatography , philosophy , linguistics
The methylene groups in 2‐(1‐azulyl)ethyl tosylate are largely scrambled prior to formation of fragment ions in the mass spectrometer. This process also occurs in the 3‐nitro analog, where it is dependent on sample residence time in the source and independent of electron energy. It could not be observed with the isomeric 6‐substituted tosylates, the 1‐substituted acetates or alcohols, or with 2‐(p‐anisyl)ethyl tosylate. Scrambling occurs in the neutral molecule prior to ionization and a mechanism involving absorption onto the metal surface and formation of a complexed ethylenazulonium ion is suggested.