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Journal Article

7H-benz [kl]acridin-7-ylium closed-shell ion produced from 1,8-bis(phenylamino)naphthalenes under electron impact: Tandem mass spectrometric structure elucidation

MPS-Authors
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Rentzea,  Marina
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Rimmler,  Gösta
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Neugebauer,  Franz A.
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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http://onlinelibrary.wiley.com/doi/10.1002/oms.1210280505/epdf
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https://dx.doi.org/10.1002/oms.1210280505
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Citation

Rentzea, M., Rimmler, G., & Neugebauer, F. A. (1993). 7H-benz [kl]acridin-7-ylium closed-shell ion produced from 1,8-bis(phenylamino)naphthalenes under electron impact: Tandem mass spectrometric structure elucidation. Organic Mass Spectrometry, 28(5), 494-498. doi:10.1002/oms.1210280505.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0019-AA65-B
Abstract
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.