Hydrolytic Stability of Hydrazones and Oximes

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. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2008/z802651_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.