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Observation of an Isolated Intermediate of the Nucleophilic Aromatic Substition Reaction by Infrared Spectroscopy
Author(s) -
Hasegawa Hayato,
Mizuse Kenta,
Hachiya Masaki,
Matsuda Yoshiyuki,
Mikami Naohiko,
Fujii Asuka
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200801751
Subject(s) - infrared , chemistry , nucleophilic aromatic substitution , nucleophile , photochemistry , nucleophilic substitution , infrared spectroscopy , ionization , spectroscopy , ultraviolet , cluster (spacecraft) , computational chemistry , ion , medicinal chemistry , organic chemistry , materials science , physics , catalysis , optics , optoelectronics , quantum mechanics , computer science , programming language
Caught in the act : The σ complex formed as an intermediate in a nucleophilic aromatic substitution has been observed experimentally. Efficient direct ionization of C 6 F 6 by coherent vacuum ultraviolet light was employed to effect the formation of C 6 F 5 NH 2 + from C 6 F 6 + /NH 3 . Comparison of the IR spectrum of (C 6 F 6 ‐NH 3 ) + with that predicted from DFT calculations showed that the cluster cation forms a stable σ complex (see picture).
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