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On the Activation of PhICl2 with Pyridine
preprintsubmitted on 19.03.2021, 01:33 and posted on 19.03.2021, 13:25 by Tiffany Poynder, Analia Orue, Tania _, Lachlan Sharp-Bucknall, Matthew Flynn, David J. D. Wilson, Kasun Athukoroala, Jack K. Clegg, Jason Dutton
It has been previously proposed that pyridines can activate PhICl2 by displacing a chloride and forming the [PhI(Pyr)(Cl)]+ cation as a reactive intermediate. Here we show that pyridine does not displace chloride, but rather forms a weak complex with the iodine via halogen bonding along the C-I bond axis. This interaction is investigated by NMR, structural, charge density and theoretical investigations, which all indicate the pyridine does not activate PhICl2 as proposed.