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Updated: Nov 8, 2025

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
On the activation of PhICl2 with pyridine
Tiffany B Poynder1, Analia I Chamorro Orué2, Tania1
1Department of Chemistry and Physics, La Trobe University, Melbourne, Victoria, 3086, Australia. j.dutton@latrobe.edu.au.
Abstract:
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 interrogated by NMR, structural, charge density, and theoretical investigations, which all indicate that pyridine does not activate PhICl2 as proposed.
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