Identification of the Aromatic Tertiary N-Oxide Functionality in Protonated Analytes via Ion/Molecule Reactions in Mass Spectrometers
Autor: | Hilkka I. Kenttämaa, Todd A. Gillespie, Penggao Duan, Brian E. Winger |
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Rok vydání: | 2008 |
Předmět: | |
Zdroj: | The Journal of Organic Chemistry. 73:4888-4894 |
ISSN: | 1520-6904 0022-3263 |
DOI: | 10.1021/jo800309u |
Popis: | 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. |
Databáze: | OpenAIRE |
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