The generation and characterization of N-succinimidooxy radical by tandem mass spectrometry in the gas phase

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T3N1

The generation and characterization of N-succinimidooxy
radical by tandem mass spectrometry in the gas phase

Dmitri V. Zagorevskiia, Curt M. Brenemana, Alexander A. Mommersb

aDepartment of Chemistry and Chemical Biology, Rensselaer Polytechnic Institute,
209C Cogswell Lab., 110 8th St., Troy, NY, U.S.A. 12180; zagord@rpi.edu
bChemistry Department, University of Ottawa, 10 Marie Curie, Ottawa, Ontario,
Canada K1N 6N5

Received: 13.09.2005; revised: 24.11.2005

Electron induced dissociation of N-hydroxysuccinimido esters of aromatic carboxylic acids resulted in the formation of the succinimidooxy radical. These radicals were detected by collision-induced dissociative ionization mass spectrometry. The initial step in the majority of fragmentation reactions of succinimidooxy ions was a loss of NO. Theoretical calculations were consistent with such behavior indicating a significant elongation of C–N bonds, and shortening of the N–O bond upon electron removal from the radical. 

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