N-alkyl-o-nitroanilines: observation of new types of ortho-effects



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Eur. J. Mass Spectrom. 4, 167 - 179 (1998)

Electron ionization-induced fragmentation of N-alkyl-o-nitroanilines: observation of new types of ortho-effects

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

ABSTRACT:
Molecular ions of N-alkyl substituted derivatives of o-nitroaniline and some of their fragment ions undergo several fragmentations which are examples of new types of ortho-effects. A fragmentation common to all studied compounds with an unbranched alkyl chain #150;CH2(CH2)nH is the formal loss of H(CH2)nCOOH (n = 03). Other important primary decomposition processes are eliminations of H2O, OH· and HO2· fragments. Reaction mechanisms for these reactions, supported by metastable and collision-induced decomposition spectra of selected model compounds and by deuterium labeling, are proposed. Other fragmentations of the molecular ion of N-alkyl-o-nitroanilines depend on the type of alkyl substituent. For alkyl larger than methyl an important process is the a-cleavage of the CC bond next to the nitrogen atom yielding the corresponding immonium cation.

Keywords: ortho-effect, fragmentation mechanisms, N-alkyl-o-nitroanilines

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