Table 2.
Binding constant KHG (103 M−1) of boronic acid hosts, KHG(S,S) with (S,S)-hydrobenzoin and KHG(R,R) with (R,R)-hydrobenzoin
Guest | Host-1 | Host (S,S)-2 | Host (R,R,R,S)-4 | Host (R)-6 | Host (S)-6 | Host (R)-8 | Host (S)-8 |
---|---|---|---|---|---|---|---|
KHG(S,S) | 1.42 ± 0.04 | 13.6 ± 0.13 | 3.55 ± 0.04 | 3.78 ± 0.06 | 6.38 ± 0.05 | 5.85 ± 0.06 | 4.17 ± 0.04 |
KHG(R,R) | 1.26 ± 0.03 | 4.77 ± 0.02 | 5.22 ± 0.07 | 5.93 ± 0.07 | 3.94 ± 0.04 | 3.96 ± 0.05 | 5.55 ± 0.06 |
All titrations were carried out in 100% MeOH, 10 mM para-toluenesulfonic acid, and Hunig's base buffer (pH 7.4). All measurements were taken at 25 °C. The error reported here results from the computer fit to the experimental isotherm. In our previous experience, there is ≈10% error, at most, in the reproducibility in the KHG value.