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19.12: Mass Spectrometry of Amines

JoVE Core
Organic Chemistry

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Mass Spectrometry of Amines

19.12: Mass Spectrometry of Amines

In mass spectroscopy, amines undergo fragmentation to give parent ions with odd molecule weights. This observed mass spectrum follows the nitrogen rule: a molecule with an odd number of nitrogen atoms produces a parent ion with an odd molecular weight. The remaining fragments have an even mass.

Amines undergo fragmentation through α cleavage, producing nitrogen-containing cations—iminium ions—and alkyl radicals. Mass spectra of aromatic and cyclic aliphatic amines exhibit strong molecular ion peaks, but acyclic aliphatic amines show weaker molecular ion peaks.


Mass Spectrometry Amines Fragmentation Parent Ions Nitrogen Rule Mass Spectrum Nitrogen Atoms Molecular Weight Fragments α-cleavage Iminium Ions Alkyl Radicals Aromatic Amines Cyclic Aliphatic Amines Acyclic Aliphatic Amines

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