<div>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.</div><div><br></div>
<div>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.</div><div><br></div>
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