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

doi:10.1002/anie.200801751

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

SCI - Chemistry

Tohoku University

Research output: Contribution to journal › Article › peer-review

20 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 language	English
Pages (from-to)	6008-6010
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	47
Issue number	32
DOIs	https://doi.org/10.1002/anie.200801751
Publication status	Published - 2008 Jul 28

Keywords

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

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10.1002/anie.200801751

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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).",

keywords = "Aromatic substitution, Gas-phase reactions, Ion-molecule reactions, IR spectroscopy, Reaction intermediates",

author = "Hayato Hasegawa and Kenta Mizuse and Masaki Hachiya and Yoshiyuki Matsuda and Naohiko Mikami and Asuka Fujii",

year = "2008",

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T1 - Observation of an isolated intermediate of the nucleophilic aromatic substition reaction by infrared spectroscopy

AU - Hasegawa, Hayato

AU - Mizuse, Kenta

AU - Hachiya, Masaki

AU - Matsuda, Yoshiyuki

AU - Mikami, Naohiko

AU - Fujii, Asuka

PY - 2008/7/28

Y1 - 2008/7/28

N2 - (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).

AB - (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).

KW - Aromatic substitution

KW - Gas-phase reactions

KW - Ion-molecule reactions

KW - IR spectroscopy

KW - Reaction intermediates

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JF - Angewandte Chemie - International Edition

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

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Keywords

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