5 years ago

Direct Experimental Evidence for Halogen–Aryl π Interactions in Solution from Molecular Torsion Balances

Direct Experimental Evidence for Halogen–Aryl π Interactions in Solution from Molecular Torsion Balances
Dieter Lentz, Han Sun, André Horatscheck, Marc Nazaré, Peter Schmieder, Max Bartetzko, Vera Martos, Ulrike Uhrig
We dissected halogen–aryl π interactions experimentally using a bicyclic N-arylimide based molecular torsion balances system, which is based on the influence of the non-bonded interaction on the equilibria between folded and unfolded states. Through comparison of balances modulated by higher halogens with fluorine balances, we determined the magnitude of the halogen–aryl π interactions in our unimolecular systems to be larger than −5.0 kJ mol−1, which is comparable with the magnitude estimated in the biomolecular systems. Our study provides direct experimental evidence of halogen–aryl π interactions in solution, which until now have only been revealed in the solid state and evaluated theoretically by quantum-mechanical calculations. Weighty evidence: Molecular torsion balances containing an N-aryl imide and an additional aromatic moiety provided direct experimental evidence for halogen–aryl π interactions in solution (see picture). The magnitude of the halogen–aryl π interactions in the unimolecular systems described herein are found to be larger than −5.0 kJ mol−1.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201700520

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