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HSAB and ionization parameters for thiolate and enolate nucleophiles
Softness (σ) and nucleophilicity (ω−; NAPQI as the reacting electrophile) for the selected compounds were calculated as described under Materials and Methods.
| Nucleophile | σ | ω– | pKa | % Anion (pH = 7.4) |
|---|---|---|---|---|
| × 10–3 ev–1 | × 10–3 ev | |||
| 2-ACP (enolate) | 418 | 485 | 7.8 | 28.5 |
| GSH (thiolate) | 427 | 548 | 8.6 | 5.9 |
| NAC (thiolate) | 367 | 667 | 9.5 | 0.8 |
