Identification of the Aromatic Tertiary N-Oxide Functionality in Protonated Analytes via Ion/Molecule Reactions in Mass Spectrometers

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• 作者：Penggao Duan ; Todd A. Gillespie ; Brian E. Winger ; Hilkka I. Kenttä ; maa
• 刊名：Journal of Organic Chemistry
• 出版年：2008
• 出版时间：July 4, 2008
• 年：2008
• 卷：73
• 期：13
• 页码：4888 - 4894
• 全文大小：211K
• 年卷期：v.73,no.13(July 4, 2008)
• ISSN：1520-6904

文摘

A mass spectrometric method is presented for the rapid identification of compounds that contain the aromatic N-oxide functional group. This method utilizes a gas-phase ion/molecule reaction with 2-methoxypropene that yields a stable adduct for protonated aromatic tertiary N-oxides (and with one protonated nitrone) in different mass spectrometers. A variety of protonated analytes with O- or N-containing functional groups were examined to probe the selectivity of the reaction. Besides protonated aromatic tertiary N-oxides and one nitrone, only three protonated amines were found to form a stable adduct but very slowly. All the other protonated analytes, including aliphatic tertiary N-oxides, primary N-oxides, and secondary N-oxides, are unreactive toward or react predominantly by proton transfer with 2-methoxypropene.