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Reactions in Nitroimidazole and Methylnitroimidazole Triggered by Low-Energy (0-8 eV) Electrons

Katrin Tanzer1, Linda Feketeová2,3, Benjamin Puschnigg1

  • 1†Institut für Ionenphysik und Angewandte Physik and Center of Molecular Biosciences, Leopold Franzens Universität Innsbruck, Technikerstrasse 25, 6020 Innsbruck, Austria.

The Journal of Physical Chemistry. A
|May 29, 2015
PubMed

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Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
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All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for...
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