Table 3. 2,5-Dimethylphenacyl (8, DMP) Photoremovable Group.
leaving group, X (protected species) | solvent | quantum yield, Φ | chemical yield of HX release (%) | kapp/s–1 a |
---|---|---|---|---|
Cl | benzene | 0.1156a (0.12)54a | 4.4 × 106 61 | |
methanol | 0.7656a (0.78)54a | 4.4 × 104 61 | ||
OC(=O)R (carboxylic acids) | benzene | 0.18–0.2554b,57b | 85–9554b | ∼257b |
methanol | 0.09–0.1457b | 9254b | 4.5 × 102 57b | |
OP(=O)(OR)2 (phosphates) | benzene | 0.0954a | ∼254a | |
methanol | 0.7154a | 9454a | 5 × 104 54a | |
OS(=O)2R (sulfonic acids) | benzene | 0.16–0.1954a | ||
methanol | 0.6854a | 90–9354a | 4 × 104 54a | |
OC(=O)OR (alcohols) | cyclohexane | 0.36–0.5158 | >7058 | b |
methanol | 0.09–0.2058 | b | ||
OC(=O)NR2 (amines) | cyclohexane | 0.054–0.08959 | b | |
acetonitrile | 0.035–0.07059 | 9759 | b | |
methanol | 0.027–0.06159 | b |
Appearance rate constant of the leaving group, calculated as kapp = 1/τenol.
Slow, presumably <1 ms–1.