Infrared spectroscopic observation of the McLafferty rearrangement in ionized 2-pentanone

文献情報

出版日 2020-08-12

DOI 10.1039/D0CP02602F

インパクトファクター 3.676

著者

Ryo Yasumoto, Yoshiyuki Matsuda, Asuka Fujii

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要旨

The McLafferty rearrangement is a well-known process in mass spectrometry. In ionization of organic molecules containing a carbonyl group, β cleavage occurs following transfer of a hydrogen atom of aliphatic CH at the γ position to the carbonyl group. Although the McLafferty rearrangement has undergone numerous mass spectrometric investigations, no spectroscopic investigation of the enolized radical cation generated in the hydrogen atom transfer has been carried out. 2-Pentanone is the simplest ketone containing CH bonds at the γ position. In this study, infrared predissociation spectroscopy for both neutral and ionized 2-pentanone in the gas phase through vacuum ultraviolet ionization detection is performed to investigate the ionization-induced isomerization and to observe the enolized product. An OH stretch band is observed in the infrared spectrum of ionized 2-pentanone, and this demonstrates its enolization accompanying the rearrangement of an alkyl hydrogen. The enolization of ionized 2-pentanone is theoretically supported by the reaction path search based on the anharmonic downward distortion following method.

掲載誌

Physical Chemistry Chemical Physics

CiteScore: 5.5

自己引用率: 10.3%

年間論文数: 3036

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