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The Nature of Azo-Substituted Carbocations: N-N π-Electron Stabilization versus Nitrogen Nonbonding Electron

Xavier Creary1

  • 1Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, United States.

The Journal of Organic Chemistry
|March 15, 2021
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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