Table 1.
Hildebrand and Molecular Dynamics solubility parameters of nicotinate acid ester prodrugs
| Compound | Molar Vaporization Energy1 (by Fedors Group Contribution) (kJ/mol) |
Molar Volume1 (by Fedors Group Contribution) (cm3/mol) |
δ (by Group Contribution) (J/cm3)1/2 |
δ (by Simulation) (J/cm3)1/2 |
|---|---|---|---|---|
| Perhydrocarbon nicotinates (Scheme 1A) |
||||
| C1F0 | 62.02 | 114.4 | 23.28 | 22.47 ± 0.33 |
| C2F0 | 66.92 | 130.5 | 22.65 | 21.82 ± 0.10 |
| C4F0 | 76.84 | 162.7 | 21.73 | 20.70 ± 0.10 |
| C6F0 | 86.72 | 194.9 | 21.09 | 20.28 ± 0.06 |
| C8F0 | 96.60 | 227.1 | 20.62 | 19.93 ± 0.05 |
| C10F0 | 106.48 | 259.3 | 20.26 | 18.88 ± 0.10 |
| C12F0 | 116.36 | 291.5 | 19.98 | 19.40 ± 0.08 |
| Perfluoroalkyl nicotinates (Scheme 1B) |
||||
| C2F3 | 66.52 | 154.5 | 20.75 | 19.97 ± 0.08 |
| C3F5 | 70.79 | 177.5 | 19.97 | 19.51 ± 0.10 |
| C4F7 | 75.06 | 200.5 | 19.35 | 18.82 ± 0.08 |
| C8F15 | 92.14 | 292.5 | 17.75 | 17.26 ± 0.09 |
| Perfluoroalkyl nicotinates (Scheme 1C) |
||||
| C3F4 | 77.78 | 162 | 21.91 | 22.43 ± 0.13 |
| C5F8 | 86.33 | 208 | 20.37 | 19.82 ± 0.18 |
| C8F13 | 92.81 | 285.6 | 18.03 | 17.85 ± 0.09 |
1
Values taken from Fedors group contribution method in ref [21]