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Type: Journal article
Title: Rearrangement and fragmentation of isomeric C4H5O anions upon collision activation: a combined experimental and ab initio study
Author: Dua, S.
Bowie, J.
Hevko, J.
Citation: European Journal of Mass Spectrometry, 2001; 7(1):7-14
Publisher: IM Publications
Issue Date: 2001
ISSN: 1469-0667
Statement of
Suresh Dua, John H. Bowie and John M. Hevko
Abstract: The 3,4-epoxybutoxide anion on collisional activation in the gas phase forms an intermediate ion complex (vinyl ethylene oxide, HO–) which eliminates water by two competitive pathways, viz. (i) by the HO– ion deprotonating the neutral to produce a vinylethylene oxide anion deprotonated on the ring adjacent to the vinyl substituent: this anion then ring opens to give –CH2–CO–CH=CH2 and (ii) by the HO– ion deprotonating at the ring methylene group to give a cyclic anion which ring opens to yield –CH2–CH=CH–CHO. In contrast, when vinyl ethylene oxide is allowed to react with HO– in the source of the mass spectrometer, deprotonation occurs mainly, if not exclusively, at the ring methylene position (as shown by deuterium labelling) to yield the anion –CH2–CH=CH–CHO. The two ring-opening processes have been investigated using theoretical studies at the MP2 Fc/6-31+G(d) level of theory.
Keywords: isomeric C4H5O anions, rearrangement, depronated methyl vinyl ketone, deprotonated crotonaldehyde
RMID: 0020010308
DOI: 10.1255/ejms.373
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Appears in Collections:Chemistry publications

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