Exceptionally rapid oxime and hydrazone formation promoted by catalytic amine buffers with low toxicity
Journal article, 2018

Hydrazone and oxime bond formation between α-nucleophiles (e.g. hydrazines, alkoxy-amines) and carbonyl compounds (aldehydes and ketones) is convenient and is widely applied in multiple fields of research. While the reactants are simple, a substantial drawback is the relatively slow reaction at neutral pH. Here we describe a novel molecular strategy for accelerating these reactions, using bifunctional buffer compounds that not only control pH but also catalyze the reaction. The buffers can be employed at pH 5-9 (5-50 mM) and accelerate reactions by several orders of magnitude, yielding second-order rate constants of >10 M-1s-1. Effective bifunctional amines include 2-(aminomethyl)imidazoles and N,N-dimethylethylenediamine. Unlike previous diaminobenzene catalysts, the new buffer amines are found to have low toxicity to human cells, and can be used to promote reactions in cellular applications.


Dennis Larsen

Stanford University

Technical University of Denmark (DTU)

Anna M. Kietrys

Stanford University

Spencer A. Clark

Stanford University

Hyun Shin Park

Stanford University

Andreas Ekebergh

Stanford University

Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry

Eric T. Kool

Stanford University

Chemical Science

2041-6520 (ISSN) 2041-6539 (eISSN)

Vol. 9 23 5252-5259

Subject Categories

Inorganic Chemistry

Other Chemistry Topics

Organic Chemistry



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Latest update

7/4/2018 1