Observation of an isolated intermediate of the nucleophilic aromatic substition reaction by infrared spectroscopy

Hayato Hasegawa, Kenta Mizuse, Masaki Hachiya, Yoshiyuki Matsuda, Naohiko Mikami, Asuka Fujii

Research output: Contribution to journalArticlepeer-review

19 Citations (Scopus)

Abstract

(Figure Presented) Caught in the act: The σ complex formed as an intermediate in a nucleophilic aromatic substitution has been observed experimentally. Efficient direct ionization of C6F6 by coherent vacuum ultraviolet light was employed to effect the formation of C 6F5NH2 + from C6F 6 +/NH3. Comparison of the IR spectrum of (C6F6-NH3)+ with that predicted from DFT calculations showed that the cluster cation forms a stable σ complex (see picture).

Original languageEnglish
Pages (from-to)6008-6010
Number of pages3
JournalAngewandte Chemie - International Edition
Volume47
Issue number32
DOIs
Publication statusPublished - 2008 Jul 28

Keywords

  • Aromatic substitution
  • Gas-phase reactions
  • IR spectroscopy
  • Ion-molecule reactions
  • Reaction intermediates

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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