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Electron ionization-induced fragmentation of N-(alkoxymethyl)anilides
Witold Danikiewicz1, Rafał Szmigielski, Marian Olejnik
1Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, P.O. Box 58, 01-224 Warsaw 42, Poland. witold@icho.edu.pl
Journal of Mass Spectrometry : JMS
|January 15, 2003
Summary
Electron ionization of N-alkoxymethylanilides reveals a primary fragmentation pathway involving alkyl radical loss, yielding protonated N-acylformanilide derivatives with high kinetic energy release. Other key fragmentations include aldehyde loss and N-methyleneaniline cation formation.
Area of Science:
- Organic Chemistry
- Mass Spectrometry
- Chemical Analysis
Background:
- N-acylaniline derivatives are important in organic synthesis.
- Understanding their fragmentation patterns under electron ionization is crucial for structural elucidation.
Purpose of the Study:
- To investigate the electron ionization-induced fragmentation patterns of N-(alkoxymethyl)acetanilides and related compounds.
- To identify the primary and secondary fragmentation pathways and their associated kinetic properties.
Main Methods:
- Electron ionization mass spectrometry was employed.
- Analysis of fragmentation patterns and kinetic energy release was performed.
Main Results:
- The dominant fragmentation pathway involves the loss of an alkyl radical from the N-alkoxymethyl group, forming protonated N-acylformanilide derivatives.
- This primary fragmentation is characterized by unusually high kinetic energy release.
- Additional fragmentation pathways include the loss of an aldehyde, elimination of a C(n)H(2n)O(2) fragment, and the formation of N-methyleneaniline radical cations.
Conclusions:
- The study elucidates the characteristic electron ionization fragmentation behavior of N-(alkoxymethyl)anilides.
- The observed fragmentation pathways provide valuable insights for the structural analysis of these compounds using mass spectrometry.