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Solvation rules: aromatic interactions outcompete cation–π interactions in synthetic host–guest complexes in water †

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Peer-reviewed

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Authors

Tobajas-Curiel, Gloria  ORCID logo  https://orcid.org/0000-0003-0022-834X
Sun, Qingqing 
Sanders, Jeremy K. M.  ORCID logo  https://orcid.org/0000-0002-5143-5210
resid: B-6436-2011 
Hunter, Christopher A.  ORCID logo  https://orcid.org/0000-0002-5182-1859

Abstract

Chemical double mutant cycles were used to measure the interaction of a N-methyl pyridinium cation with a π-box in a calix[4]pyrrole receptor. Although the cation–π interaction is attractive (−11 kJ mol−1), it is 7 kJ mol−1 less favourable than the corresponding aromatic interaction with the isosteric but uncharged tolyl group.

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Publisher

The Royal Society of Chemistry
Sponsorship
Agència de Gestió d'Ajuts Universitaris i de Recerca (2017 SGR 1123)
Generalitat de Catalunya (Unassigned)