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- Title
Synergic Interplay Between Halogen Bonding and Hydrogen Bonding in the Activation of a Neutral Substrate in a Nanoconfined Space.
- Authors
La Manna, Pellegrino; De Rosa, Margherita; Talotta, Carmen; Rescifina, Antonio; Floresta, Giuseppe; Soriente, Annunziata; Gaeta, Carmine; Neri, Placido
- Abstract
The principle of amplified halogen bonding (XB) in a small space is exploited as a catalytic tool for the activation of an XB acceptor substrate in a nanoconfined environment. The inner cavity of the resorcinarene capsule has been equipped with an XB catalyst bearing an ammonium unit acting as a Trojan horse to drive the catalyst inside the capsule. In the presence of a specific XB catalyst, the capsule is able to catalyze a Michael reaction between N‐methylpyrrole and methyl vinyl ketone. In the bulk medium in absence of the resorcinarene capsule, the XB catalyst is catalytically ineffective. Quantum‐mechanical investigations highlight that the Michael reaction proceeds through the activation of the carbonyl group by synergistically enhanced halogen/hydrogen‐bonding interactions and takes place in an open pentameric capsule.
- Subjects
HYDROGEN bonding; METHYL vinyl ketone; MICHAEL reaction; HALOGENS; CARBONYL group; ATOMIC hydrogen
- Publication
Angewandte Chemie, 2020, Vol 132, Issue 2, p821
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201909865