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

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).