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Keywords:

  • hydrazones;
  • hydrolysis;
  • oximes;
  • reaction mechanisms
Thumbnail image of graphical abstract

Watching C 'n' N: Hydrazones and oximes are common conjugates but are labile to hydrolysis. The hydrolytic stabilities of isostructural hydrazones and one oxime were determined at pD 5.0–9.0. The rate constant for the acid-catalyzed hydrolysis of the oxime was nearly 103-fold lower than those for simple hydrazones, and a trialkylhydrazonium ion (formed after condensation) was even more stable than the oxime.