Journal article
Formation and chlorination of carbazole, phenoxazine, and phenazine
Environmental Science & Technology, Vol.49(4), pp.2215-2221
2015
Abstract
This contribution presents pathways for the formation of the three nitrogenated dioxin-like species, carbazole, phenoxazine, and phenazine via unimolecular rearrangements of diphenylamine (DPA) and its nitro substituents (NDPA). The latter represent major structural entities appearing in formulations of explosives and propellants. Intramolecular H transfer from the amine group to one of the two O atoms in the nitro group denotes the most accessible route in the unimolecular decomposition of NDPA. Further unimolecular rearrangements afford phenazine and carbazole. A loss of an ortho substituent from DPA, followed by addition of an oxygen molecule, prompts the formation of carbazole and phenoxazine in a facile mechanism. The consistency between trends in Fukui-based electrophilic indices and the experimental profiles of chlorinated carbazole, phenoxazine, and phenazine suggests the formation of these species by electrophilic substitution.
Details
- Title
- Formation and chlorination of carbazole, phenoxazine, and phenazine
- Authors/Creators
- M. Altarawneh (Author/Creator)B.Z. Dlugogorski (Author/Creator)
- Publication Details
- Environmental Science & Technology, Vol.49(4), pp.2215-2221
- Publisher
- American Chemical Society
- Grant note
- Grant ID: DP140104492
- Identifiers
- 991005541974907891
- Copyright
- © 2015 American Chemical Society
- Murdoch Affiliation
- School of Engineering and Information Technology
- Language
- English
- Resource Type
- Journal article
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