Formation and chlorination of carbazole, phenoxazine, and phenazine
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 formulation...
Ausführliche Beschreibung
Gespeichert in:
| Autor*in: |
Dlugogorski, Bogdan Z [verfasserIn] |
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| Format: |
Artikel |
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| Sprache: |
Englisch |
| Erschienen: |
2015 |
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| Schlagwörter: |
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| Übergeordnetes Werk: |
Enthalten in: Environmental science & technology - Washington, DC : ACS Publ., 1967, 49(2015), 4, Seite 2215 |
|---|---|
| Übergeordnetes Werk: |
volume:49 ; year:2015 ; number:4 ; pages:2215 |
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| 520 | |a 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. | ||
| 650 | 4 | |a Diphenylamine - chemistry | |
| 650 | 4 | |a Carbazoles - chemistry | |
| 650 | 4 | |a Tetrachlorodibenzodioxin - chemistry | |
| 650 | 4 | |a Oxazines - chemistry | |
| 650 | 4 | |a Phenazines - chemistry | |
| 650 | 4 | |a Chlorine | |
| 650 | 4 | |a Oxygen | |
| 650 | 4 | |a Molecules | |
| 650 | 4 | |a Organic chemicals | |
| 650 | 4 | |a Trends | |
| 650 | 4 | |a Decomposition | |
| 700 | 1 | |a Altarawneh, Mohammednoor |4 oth | |
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Formation and chlorination of carbazole, phenoxazine, and phenazine |
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Dlugogorski, Bogdan Z |
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Environmental science & technology |
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Environmental science & technology |
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Dlugogorski, Bogdan Z |
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050 333.7 |
| title_sort |
formation and chlorination of carbazole, phenoxazine, and phenazine |
| title_auth |
Formation and chlorination of carbazole, phenoxazine, and phenazine |
| 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. |
| abstractGer |
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. |
| abstract_unstemmed |
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. |
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4 |
| title_short |
Formation and chlorination of carbazole, phenoxazine, and phenazine |
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http://www.ncbi.nlm.nih.gov/pubmed/25584392 http://search.proquest.com/docview/1658066481 |
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Altarawneh, Mohammednoor |
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