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Fragmentation of o-nitrodiarylamines on electron impact: Formation of carbazole radical cations

✍ Scribed by Ryszard Gawiuecki; Danuta Rasaia; Tomasz Bąk

Publisher
John Wiley and Sons
Year
1992
Tongue
English
Weight
413 KB
Volume
27
Category
Article
ISSN
1076-5174

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✦ Synopsis

The H O fragment eliminated on electron impact (EI) from the molecular ions of o-nitrodiarylamines contains either the amine or the aryl hydrogen. Moreover, 2-phenylamino-lnitropyridine loses H from the pheoyl group. As confirmed by collision-activated dissociation mass-analysed ion kinetic energy spectra, the fragmentation of such compounds involves the formation of carbazole radical cations. Such a process was not observed for the corresponding o-aminodiarylamines.

EI-induced fragmentation was investigated. Collision techniaues were used to confirm the structure4 of the INTRODUCTION

Diarylamines lose two hydrogen atoms on electron impact (EI) to give the respective carbazole radical cation.' Dibenzofurans' and thiophenes3 are formed with o-nitro-substituted diary1 ethers and sulphides expel HNO,. Formation of the respective aza heterocycles was suggested to take place in EI-induced fragmentation of 2-and 4-phenylamino-3-nitropyridines." It was proved recently' that N-(0-nitropheny1)-p-amino- benzoic acid loses successively HO' and NO' under similar conditions to form the respective carbazole carboxylic acid radical cation.

In this work, some new o-nitrodi(heter0)arylamines prod& of NHO, elimination from the molecular ions of the compounds under study. The formation of carbazole ions from o-nitroarylamine molecular ions is analogous to the Pschorr rea~tion.~.'

RESULTS AND DISCUSSION

The loss of HNO, from 2-and 4-phenylamino-3-nitropyridine on EI can be a one-or a two-step p r o ~e s s . ~

This paper discusses the EI-induced formation of carbazole radical cations from a series of nitrodiarylamines and their deutero analogues were prepared and their (1-12; R' = 0) (Scheme 1).

No.

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