ISSN:
0030-493X
Keywords:
Chemistry
;
Analytical Chemistry and Spectroscopy
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Not only strongly basic aromatic amines such as ‘proton sponges’ show characteristic [M - Me2NH - H]+ peaks corresponding to cyclization to stable heterocyclic ions under electron impact. The fragmentation of the title compounds, which are weak bases, leads to [M - RNH2 - C6H5]+ heteroaromatic ions. These are the 7-phenyl-7H-benz[kl]acridine radical cation and the delocalized stable 7H-benz[kl]acridin-7-ylium ion as shown by unimolecular metastable ion spectra, collision-induced decomposition (CID) tandem mass spectrometry (MS/MS) and accurate mass measurements. The high-collision-energy CID tandem mass spectra of these ions are perfectly superimposable on those of the ions produced by the reference substance, 7-phenyl-7H-benz[kl]acridine obtained as a by-product in the Ullmann phenylation of 1,8-diaminonaphthalene. This combination of MS/MS experiments also provides strong support for the gas-phase reaction mechanism leading to the benz[kl]acridine ions and for the structures of these ions.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/oms.1210280505
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