Table 1.
Thiazolium Coenzyme Mimics (14) | ||||||
---|---|---|---|---|---|---|
Entry | R1 | R2 | X | PEI | V (×10−9 M/s) | krelb |
1c | C12H25 | BnO | Br | - | 4 | 1 |
2 | C12H25 | BnO | Br | 11 | 5040 ± 60 | 1260 ± 15 |
3 | C12H25 | BnO | Br | 13 | 5136 ± 111 | 1284 ± 28 |
4d | C12H25 | BnO | Br | 11 | 5167 ± 222 | 1304 ± 56 |
5 | C12H25 | BnO | I | 11 | 4944 ± 111 | 1248 ± 28 |
6 | Bn | BnO | Cl | 11 | 24 ± 2 | 6 ± 0.5 |
7 | Me | C12H25S | I | 11 | 552 ± 56 | 138 ± 14 |
8 | C4H9 | C12H25S | I | 11 | 9424 ± 524 | 2356 ± 131 |
9 | C6H13 | C12H25S | I | 11 | 4664 ± 40 | 1166 ± 10 |
10 | Bn | C12H25S | Br | 11 | 1552 ± 16 | 388 ± 4 |
11 | C4H9 | C12H25S | I | 12 | 596 ± 16 | 149 ± 4 |
Imidazolium Coenzyme Mimics (4) | ||||||
Entry | R | X | PEI | V (×10−9 M/s) | krelb | |
12 | Me | I | - | 0.36 | 1 | |
13 | C4H9 | I | 13 | 13 ± 0.17 | 37 ± 0.5 | |
14 | C6H13 | I | 13 | 18.7 ± 0.33 | 52 ± 1 | |
15 | C8H17 | I | 13 | 44 ± 2 | 123 ± 6 | |
16 | C10H21 | I | 13 | 833 ± 11 | 2314 ± 31 | |
17 | C12H25 | I | 13 | 1225 ± 3 | 3402 ± 8 | |
18 | C12H25 | I | 11 | 83 ± 5 | 230 ± 14 |
Coenzyme loading = 10 mol % (14), 40 mol % (4); [PEI] = 6 mM; [PhCHO]initial = 40mM.
Relative to entry 1 or 12, respectively. Errors are the deviations from two runs.
One run.
Buffer concentration = 0.2M Na2HPO4 (pH~8.0).
Calculated from the initial slope of [Benzoin] vs. time. Errors are the deviations from two runs.