Journal article
Dehalogenation of aromatics by nucleophilic aromatic substitution.
- Sadowsky D Institute of Biogeochemistry and Pollutant Dynamics, ETH Zurich , 8092 Zurich, Switzerland.
- McNeill K
- Cramer CJ
- 2014-08-19
Published in:
- Environmental science & technology. - 2014
Anions
Benzene
Environment
Halogenation
Hydrocarbons, Aromatic
Organic Chemistry Phenomena
Solutions
Thermodynamics
English
Nucleophilic aromatic substitution has been implicated as a mechanism for both the biotic and abiotic hydrodehalogenation of aromatics. Two mechanisms for the aqueous dehalogenation of aromatics involving nucleophilic aromatic substitution with hydride as a nucleophile are investigated using a validated density functional and continuum solvation protocol. For chlorinated and brominated aromatics, nucleophilic addition ortho to carbon-halogen bonds via an anionic intermediate is predicted to be the preferred mechanism in the majority of cases, while concerted substitution is predicted to be preferred for most fluorinated aromatics. Nucleophilic aromatic substitution reactions with the hydroxide and hydrosulfide anions as nucleophiles are also investigated and compared.
- Language
-
- English
- Open access status
- closed
- Identifiers
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- DOI 10.1021/es5028822
- PMID 25133312
- Persistent URL
- https://sonar.ch/global/documents/229237
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