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

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.

Tobajas-Curiel, G.; Sun, Q. Q.; Sanders, J. K. M.; Ballester, P.; Hunter, C. A.

Chem. Commun. 2023, 59 (95), 14146-14148
DOI: 10.1039/D3CC04399A

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