Ortho interactions during fragmentation of N-(2-nitrophenyl)-methane sulfonamide and its N-alkyl derivatives upon electronionization

Eur. J. Mass Spectrom. 3, 209–216 (1997)
DOI: 10.1255/ejms.13

Ortho interactions during fragmentation of N-(2-nitrophenyl)-methane sulfonamide and its N-alkyl derivatives upon electronionization

Witold Danikiewicz
Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, 01-224 Warszawa 42, PO Box 58, Poland.

ABSTRACT:

Fragmentation patterns upon electron ionization of N-(2-nitrophenyl)-methane sulfonamide and selected N-alkyl-N-(2-nitrophenyl)-methane sulfonamides are described. It is observed that the molecular ions of the latter compounds undergo rearrangement reactions resulting in the loss of the molecule of an appropriate carbonyl compound. The molecular ion of N-(2-nitrophenyl)-methane sulfonamide also undergoes rearrangement reaction yielding a benzofurazane radical cation. Proposals for the appropriate "ortho-effect" based reaction mechanisms are given.

Keywords: ortho-effect, fragmentation mechanisms,o-nitroaniline derivatives.

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