Aniline Catalysed Hydrazone Formation Reactions Show a Large Variation in Reaction Rates and Catalytic Effects

Journal article (2018)

Authors

F. Trausel ChemE/Advanced Soft Matter - AS
B. Fan ChemE/Advanced Soft Matter - AS
S.A.P. van Rossum ChemE/Advanced Soft Matter - AS
J.H. van Esch ChemE/Advanced Soft Matter - AS
R. Eelkema ChemE/Advanced Soft Matter - AS
Research Group
ChemE/Advanced Soft Matter (AS) (TU Delft)
Copyright: © 2018 F. Trausel, B. Fan, S.A.P. van Rossum, J.H. van Esch, R. Eelkema
DOI
help_outline
https://doi.org/10.1002/adsc.201800342
Bioorthogonal chemistry Click chemistry Hydrazones Organocatalysis UV/vis spectroscopy
More Info
expand_more

Published Date

2018

Language

English

Reuse Rights

Other than for strictly personal use, it is not permitted to download, forward or distribute the text or part of it, without the consent of the author(s) and/or copyright holder(s), unless the work is under an open content license such as Creative Commons.

Faculty

Applied Sciences

Department

ChemE/Chemical Engineering

Research Group

ChemE/Advanced Soft Matter

Abstract

Hydrazone formation reactions from aldehydes and hydrazides have the remarkable qualities that they proceed in water and the kinetics can be controlled by organocatalysis. For these reasons, this class of reactions finds widespread use in biological as well as material settings. We recently reported a protected aniline catalyst for hydrazone formation that can be activated using a chemical signal. In our search to find a suitable hydrazone formation reaction to investigate the activation of this pro-catalyst, we found a wide variety in reaction rates and response to catalysis. Here we report an overview of hydrazone formation reactions, their reaction rates and response to aniline catalysis, their compatibility for kinetic analysis by UV/Vis spectroscopy, and their compatibility with the reaction environment and with the pro-catalyst pro-aniline.