Interactions between Functional Groups Part IV. The responses of four diazonium groups to adjacent electron-rich atoms in peri-substituted naphthalene and quinoline derivatives

Authors

  • John D. Wallis,

    Corresponding author
    1. Laboratorium für Organische Chemie, ETH-Zentrum, Universitätstrasse 16, CH–8092 Zürich
    Current affiliation:
    1. Chemical Laboratory, University of Kent, Canterbury CT2 7NH, England
    • Laboratorium für Organische Chemie, ETH-Zentrum, Universitätstrasse 16, CH–8092 Zürich
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  • Robert J. C. Easton,

    1. Laboratorium für Organische Chemie, ETH-Zentrum, Universitätstrasse 16, CH–8092 Zürich
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  • Jack D. Dunitz

    Corresponding author
    1. Laboratorium für Organische Chemie, ETH-Zentrum, Universitätstrasse 16, CH–8092 Zürich
    • Laboratorium für Organische Chemie, ETH-Zentrum, Universitätstrasse 16, CH–8092 Zürich
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Abstract

Four peri-substituted naphthalene-1-diazonium cations all show short attractive interactions between an electron-rich atom of the peri-substituent and the α -N-atom of the diazonium group. These are interpreted as models for incipient nucleophilic attack on a N[TRIPLE BOND]N bond. The diazonium group is a better acceptor of electron density ‘through space’ than the NO2 group, which parallels their relative ‘through-σ-bond’ inductive effects.

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