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
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