Issue 6, 2021

Accelerated reactions of amines with carbon dioxide driven by superacid at the microdroplet interface

Abstract

Microdroplets display distinctive interfacial chemistry, manifested as accelerated reactions relative to those observed for the same reagents in bulk. Carbon dioxide undergoes C–N bond formation reactions with amines at the interface of droplets to form carbamic acids. Electrospray ionization mass spectrometry displays the reaction products in the form of the protonated and deprotonated carbamic acid. Electrosonic spray ionization (ESSI) utilizing carbon dioxide as nebulization gas, confines reaction to the gas–liquid interface where it proceeds much faster than in the bulk. Intriguingly, trace amounts of water accelerate the reaction, presumably by formation of superacid or superbase at the water interface. The suggested mechanism of protonation of CO2 followed by nucleophilic attack by the amine is analogous to that previously advanced for imidazole formation from carboxylic acids and diamines.

Graphical abstract: Accelerated reactions of amines with carbon dioxide driven by superacid at the microdroplet interface

Supplementary files

Article information

Article type
Edge Article
Submitted
10 10 2020
Accepted
19 12 2020
First published
21 12 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2021,12, 2242-2250

Accelerated reactions of amines with carbon dioxide driven by superacid at the microdroplet interface

K. Huang, Z. Wei and R. G. Cooks, Chem. Sci., 2021, 12, 2242 DOI: 10.1039/D0SC05625A

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