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Similarities and differences in the electron ionization-induced fragmentation of structurally related N-alkoxymethyl lactams and sultams.
J Mass Spectrom. 2005 Mar; 40(3):331-41.JM

Abstract

Unimolecular fragmentation patterns of the molecular ions of selected lactams and sultams bearing alkoxymethyl group at the nitrogen atom were studied. The main common fragmentation reaction observed for all compounds studied in this work is the elimination of an aldehyde molecule. This reaction is considered to proceed via two different mechanisms. For lactams, hydrogen rearrangement within an alkoxymethyl group is observed, which leads to the appropriate N-methyl derivatives. For sultams, transfer of the methyl group to the nitrogen and oxygen atoms, proceeding through an ion-neutral complex, dominates. Another important fragmentation channel characteristic exclusively for lactams is the loss of an alkyl radical. This process takes place within the N-alkoxymethyl moiety, yielding the appropriate protonated ion of N-formyllactams. This process is accompanied by relatively high kinetic energy release.

Authors+Show Affiliations

Institute of Organic Chemistry, Polish Academy of Sciences ul. Kasprzaka 44/52, P.O. Box 58, 01-224 Warsaw 42, Poland.No affiliation info available

Pub Type(s)

Comparative Study
Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

15685643

Citation

Szmigielski, Rafał, and Witold Danikiewicz. "Similarities and Differences in the Electron Ionization-induced Fragmentation of Structurally Related N-alkoxymethyl Lactams and Sultams." Journal of Mass Spectrometry : JMS, vol. 40, no. 3, 2005, pp. 331-41.
Szmigielski R, Danikiewicz W. Similarities and differences in the electron ionization-induced fragmentation of structurally related N-alkoxymethyl lactams and sultams. J Mass Spectrom. 2005;40(3):331-41.
Szmigielski, R., & Danikiewicz, W. (2005). Similarities and differences in the electron ionization-induced fragmentation of structurally related N-alkoxymethyl lactams and sultams. Journal of Mass Spectrometry : JMS, 40(3), 331-41.
Szmigielski R, Danikiewicz W. Similarities and Differences in the Electron Ionization-induced Fragmentation of Structurally Related N-alkoxymethyl Lactams and Sultams. J Mass Spectrom. 2005;40(3):331-41. PubMed PMID: 15685643.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Similarities and differences in the electron ionization-induced fragmentation of structurally related N-alkoxymethyl lactams and sultams. AU - Szmigielski,Rafał, AU - Danikiewicz,Witold, PY - 2005/2/3/pubmed PY - 2005/5/20/medline PY - 2005/2/3/entrez SP - 331 EP - 41 JF - Journal of mass spectrometry : JMS JO - J Mass Spectrom VL - 40 IS - 3 N2 - Unimolecular fragmentation patterns of the molecular ions of selected lactams and sultams bearing alkoxymethyl group at the nitrogen atom were studied. The main common fragmentation reaction observed for all compounds studied in this work is the elimination of an aldehyde molecule. This reaction is considered to proceed via two different mechanisms. For lactams, hydrogen rearrangement within an alkoxymethyl group is observed, which leads to the appropriate N-methyl derivatives. For sultams, transfer of the methyl group to the nitrogen and oxygen atoms, proceeding through an ion-neutral complex, dominates. Another important fragmentation channel characteristic exclusively for lactams is the loss of an alkyl radical. This process takes place within the N-alkoxymethyl moiety, yielding the appropriate protonated ion of N-formyllactams. This process is accompanied by relatively high kinetic energy release. SN - 1076-5174 UR - https://www.unboundmedicine.com/medline/citation/15685643/Similarities_and_differences_in_the_electron_ionization_induced_fragmentation_of_structurally_related_N_alkoxymethyl_lactams_and_sultams_ L2 - https://doi.org/10.1002/jms.790 DB - PRIME DP - Unbound Medicine ER -