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Hydrolytic Stability of Hydrazones and Oximes

Authors


  • We are grateful to Prof. W. W. Cleland, Prof. S. F. Nelsen, M. D. Shoulders, and T. J. Rutkoski for contributive discussions, and Dr. C. G. Fry for providing laboratory space and unconstrained access to NMR spectrometers in the Department of Chemistry. This work was supported by NIH grant GM044783 and the Materials Research Science and Engineering Center at the University of Wisconsin-Madison (NSF DMR-0520527). The Magnetic Resonance Facility was supported by NSF grant CHE-9208463 and NIH grant RR08389. NMRFAM was supported by NIH grant P41RR02301.

Abstract

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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.

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