Table 4.
ΔErxn in kcal/mol for bimolecular reaction with OH producing water and chlorinated phenoxyl radical. The values for phenol are also reported for reference. Values relative to phenol are given in parentheses. The model chemistries are B3LYP/6-31G(d,p) (I), BHandHLYP/6-31G(d,p) (II), BHandHLYP/aug-cc-pVDZ (III) and QCISD(T)/6-31G(d,p)// BHandHLYP/6-31G(d,p) (IV).
| Compound | I | II | III | IV |
|---|---|---|---|---|
| Phenol | −30.4 | −26.6 | −28 | −26.5 |
| 2-Chlorophenol | −28.6 (+1.8) | −24.4 (+2.2) | −25.6 (+2.4) | −24.9 (+1.6) |
| 3-Chlorophenol | −29.3 (+1.1) | −25.4 (+1.2) | −26.9 (+1.1) | −25.4 (+1.1) |
| 4-Chlorophenol | −31.0 (−0.6) | −26.8 (−0.2) | −28.6 (−0.6) | −27.0 (−0.5) |
| 2,3-Dichlorophenol | −28.0 (+2.4) | −23.6 (+3.0) | −24.9 (+3.1) | |
| 2,4-Dichlorophenol | −29.4 (+1.0) | −24.7 (+1.9) | −26.3 (+1.7) | |
| 2,5-Dichlorophenol | −27.8 (+2.6) | −23.3 (+3.3) | −24.7 (+3.3) | |
| 2,6-Dichlorophenol | −29.9 (+0.5) | −25.1 (+1.5) | −26.3 (+1.7) | |
| 3,4-Dichlorophenol | −30.1 (+0.3) | −25.7 (+0.9) | −27.6 (+0.4) | |
| 3,5-Dichlorophenol | −28.2 (+2.2) | −24.2 (+2.4) | −25.8 (+2.2) | |
| 2,3,4-Trichlorophenol | −28.8 (+1.6) | −23.9 (+2.7) | −25.6 (+2.4) | |
| 2,3,5-Trichlorophenol | −27.1 (+3.3) | −22.6 (+4.0) | −24.0 (+4.0) | |
| 2,3,6-Trichlorophenol | −29.4 (+1.0) | −24.5 (+2.1) | −25.8 (+2.2) | |
| 2,4,5-Trichlorophenol | −28.7 (+1.7) | −23.8 (+2.8) | −25.5 (+2.5) | |
| 2,4,6-Trichlorophenol | −30.8 (−0.4) | −25.5 (+1.1) | −27.2 (+0.8) | |
| 3,4,5-Trichlorophenol | −29.2 (+1.2) | −24.6 (+2.0) | −26.6 (+1.4) | |
| 2,3,4,5-Tetrachlorophenol | −23.0 (+3.6) | −24.7 (+3.3) | ||
| 2,3,5,6-Tetrachlorophenol | −23.9 (+2.7) | −25.3 (+2.7) | ||
| 2,3,4,6-Tetrachlorophenol | −24.9 (+1.7) | −26.5 (+1.5) | ||
| Pentachlorophenol | −24.3 (+2.3) | −26.0 (+2.0) |