Studies in organic mass spectrometry. Part 23.

^a Role of the aroyl group on the competitive fragmentation reactions of the molecular ion of aroylanilides

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Eur. J. Mass Spectrom. 5, 89 - 92 (1999)

Studies in organic mass spectrometry. Part 23.^a Role of the aroyl group on the competitive fragmentation reactions of the molecular ion of aroylanilides

Leopoldo Ceraulo, Vita Di Stefano and Mirella Ferrugia
Dipartimento di Chimica e Tecnologie Farmaceutiche, Via Archirafi 32, I-90123 Palermo, Italy.
Salvatore Foti and Rosaria Saletti
Dipartimento di Scienze Chimiche, Viale A. Doria 6, I-95125 Catania, Italy.
Domenico Spinelli^*
Dipartimento di Chimica Organica "A. Mangini", Via San Donato 15, I-40127 Bologna, Italy.

ABSTRACT:

The 70 eV and mass-analysed ion kinetic energy (MIKE) spectra of some thiophenecarboxanilides and benzoylanilides (110) have been compared in order to investigate the role of the aroyl (or heteroaroyl) moiety on the abundance of the competitive fragmentation reactions occurring in their molecular ions (amidebond cleavage and phenol radical ion formation). It has been shown that the electron ionisation induced decompositions with high (70 eV) and low (MIKE) internal energy excess are qualitatively similar, but remarkable quantitative differences have been observed that can be accounted for in terms of the different effectiveness in the transmission of electronic effects of substituents in the thiophene and benzene rings.

Keywords: electron ionisation, positive ions, ion chemistry, aroylanilides, substituent effects, rearrangement processes.

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