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Eur. J. Mass Spectrom. 2, 295 - 300 (1996)

Mass spectrometry of some fluorinated pyridinium N-imines

Giuseppe Resnati and Barbara Novo
CNR, Centro di Studio per le Sostanze Organiche Naturali, Dipartimentodi Chimica del Politecnico, Via Mancinelli 7, I-20133 Milano, Italy.
Donata Favretto
CNR, Area di Ricerca, Corso Stati Uniti 4, I-35020 Padova, Italy.
Pietro Traldi
CNR, Centro di Studio sulla Stabilità e Reattività dei Composti di Coordinazione, Via Marzolo 1, I-35100 Padova, Italy.

ABSTRACT:
Four fluorinated pyridinium-N-imines have been studied under both electron ionisation and fast atom bombardment conditions, with the aim of evaluating the role of fluorine in the stabilisation of the possible canonical forms of the resonance hybrid. The data obtained suggest that the presence of a fluorinated substituent increases the contribution of the form bearing the negative charge on the oxygen atom. Electron impact data, in particular the highly favoured formation of [M H]+ ions and the presence of specific fragmentation channels, different from the ones described in the literature for non-fluorinated analogues, are in agreement with this hypothesis. Fast atom bombardment data indicate that protonation activates severe structural modifications, responsible for decomposition processes that are not easily explained.

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