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Strong halogen bond (XB) donors are needed for the activation of neutral substrates. We demonstrate that XB donor properties of iodo-triazoles can be significantly enhanced by quaternization in combination with varying the counterion and aromatic substituent, exemplified by association constants with quinuclidine as high as 1.1 × 10 4 M -1 .

Tunable chiral triazole-based halogen bond donors: assessment of donor strength in solution with nitrogen-containing acceptors