Infrared Spectroscopic Observation Of The Mclafferty Rearrangement In Ionized 2-pentanone
Matsuda, Yoshiyuki
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https://hdl.handle.net/2142/111216
Description
Title
Infrared Spectroscopic Observation Of The Mclafferty Rearrangement In Ionized 2-pentanone
Author(s)
Matsuda, Yoshiyuki
Contributor(s)
Fujii, Asuka
YASUMOTO, RYO
Issue Date
2021-06-22
Keyword(s)
Ions
Abstract
The McLafferty rearrangement is a well-known process in mass spectrometry. The Mclafferty rearrangement is dissociations of ionized ketones with accompanying hydrogen transfer on the gamma carbon atom to generate an enol cation. This reaction has undergone numerous mass spectrometric investigations but there has been no spectroscopic research to observe the intermediate enol cation. In this study, we have performed infrared spectroscopy of jet-cooled neutral and ionized 2-pentanone to investigate its isomerization process following photoionization. The OH stretch bands as well as CH stretch bands are observed in the spectrum of cationic 2-pentanone, while only CH stretch bands are observed for the neutral. These clearly indicate the enolization following hydrogen transfer from CH occurs in the ionized pentanone. The enolization of ionized 2-pentanone through hydrogen transfer from the gamma carbon is also supported by the theoretical reaction path search calculation.
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