HSAB and ionization parameters for thiolate and enolate nucleophiles
Softness (σ) and nucleophilicity (ω−; acrolein as the reacting electrophile) for the selected compounds were calculated as described in Materials and Methods.
| Softness (σ × 103 ev−1) | Nucleophilicity (ω− × 103 ev) | pKa | % Anion (pH = 7.4) | |
|---|---|---|---|---|
| 2-ACP (enolate) | 418 | 204 | 7.8 | 28.5 |
| GSH (thiolate) | 427 | 239 | 8.6 | 5.9 |
| NAC (thiolate) | 367 | 316 | 9.5 | 0.8 |