Dehalogenation of aromatics by nucleophilic aromatic substitution

Daniel Sadowsky, Kristopher McNeill, Chris Cramer

Research output: Contribution to journalArticlepeer-review

27 Scopus citations

Abstract

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 carbonhalogen 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.

Original languageEnglish (US)
Pages (from-to)10904-10911
Number of pages8
JournalEnvironmental Science and Technology
Volume48
Issue number18
DOIs
StatePublished - Sep 16 2014

Bibliographical note

Publisher Copyright:
© 2014 American Chemical Society.

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