Identification of an intact sydnonimine ring depending on the reaction substituents of mesocarb by gas chromatography/mass spectrometry

JeongAe Lee, Hyeonsook Jeung, Keon Kim, Dong Seok Lho

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Trifluoroacylated, trimethylsilylated and methylated mesocarb (3-(1-methyl-2-phenylethyl)-5-[[(phenylamino carbonyl]amino]-1,2,3-oxadiazolium) were analyzed by gas chromatography/mass spectrometry (GC/MS). In trifluoroacylation, N-trifluoroacylated sydnophen (SP-NTFA), where the exocyclic nitrogen atom of the sydnonimine ring attacks N-methylbis(trifluoroacetamide), was identified by GC/MS. However, in trimethylsilylation, C-trimethylsilylated sydnophen (SP-CTMS), where the C-4 atom of the sydnonimine ring attacks N-methyl-N-trimethylsilyltrifluoroacetamide, was detected. SP-NTFA and SP-CTMS are intermediates of mesocarb in pyrolysis, and retain an intact sydnonimine ring. In methylation, a ketene form of mesocarb reacts as a nucleophile with methyl iodide to produce methylated N-nitroso-N-cyanomethylamphetamine. Thus, depending on the reaction substituents, the intermediate of mesocarb in pyrolysis was identified to be either an intact sydnonimine ring skeleton or an open-ring compound using GC/MS.

Original languageEnglish
Pages (from-to)1079-1086
Number of pages8
JournalJournal of Mass Spectrometry
Volume34
Issue number10
DOIs
Publication statusPublished - 1999 Jan 1

Fingerprint

Gas chromatography
Gas Chromatography-Mass Spectrometry
Mass spectrometry
Pyrolysis
Atoms
Nucleophiles
Methylation
Skeleton
Nitrogen
sidnocarb
sydnophen
cyclohexane-1,2,4-tris(methylenesulfonate)

Keywords

  • Intact sydnonimine ring
  • Mesocarb intermediate
  • Methylated N-nitroso-N-cyanomethylamphetamine
  • Pyrolysis
  • Trifluoroacylated sydnophen
  • Trimethylsilylated sydnophen

ASJC Scopus subject areas

  • Biophysics
  • Organic Chemistry
  • Spectroscopy

Cite this

Identification of an intact sydnonimine ring depending on the reaction substituents of mesocarb by gas chromatography/mass spectrometry. / Lee, JeongAe; Jeung, Hyeonsook; Kim, Keon; Lho, Dong Seok.

In: Journal of Mass Spectrometry, Vol. 34, No. 10, 01.01.1999, p. 1079-1086.

Research output: Contribution to journalArticle

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