Acid-Base Catalysis in the Mechanochemical Formation of a Reluctant Imine

Understanding the mechanism of action of catalytic amounts of additives on mechanochemical reactions is a growing and increasingly important topic in mechanochemistry, because it allows a significant level of control over the course and selectivity of mechanochemical reactions. Here, we investigate...

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Bibliographic Details
Published in:Croatica Chemica Acta 2022-12, Vol.95 (4), p.141-145
Main Authors: Vugrin, Leonarda, Cvrtila, Ivica, Juribašić Kulcsár, Marina, Halasz, Ivan
Format: Article
Language:English
Subjects:
acid-base catalysis
Catalysis
imine
mechanism
mechanochemistry
Organic acids
Raman monitoring
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Summary:Understanding the mechanism of action of catalytic amounts of additives on mechanochemical reactions is a growing and increasingly important topic in mechanochemistry, because it allows a significant level of control over the course and selectivity of mechanochemical reactions. Here, we investigate catalysis in the mechanochemical formation of an imine derived from p-nitrobenzaldehyde and p-nitroaniline, which did not occur by neat grinding at room temperature. Based on in situ reaction monitoring and DFT computations, we explain efficient catalysis observed for carboxylic acids, which suitably position the reacting partners and facilitate proton transfer. We also observe the formation of an aminal intermediate and conclude that the final elimination step in imine formation may proceed from either the hemiaminal or the aminal. Keywords: imine, mechanochemistry, acid-base catalysis, mechanism, Raman monitoring.
ISSN:0011-1643
1334-417X
DOI:10.5562/cca3954