Table 3.
ΔErxn in kcal/mol for bimolecular reaction with a hydrogen atom producing OH and chlorobenzene. 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 | −2.3 | −7.7 | −8.5 | |
| 2-Chlorophenol | −1.5 (+0.8) | −7.0 (+0.7) | −7.8 (+0.7) | −5.2 (+1.0) |
| 3-Chlorophenol | −2.5 (−0.2) | −7.9 (−0.2) | −8.7 (−0.2) | −6.3 (−0.1) |
| 4-Chlorophenol | −2.8 (−0.5) | −8.2 (−0.5) | −9.1 (−0.6) | −6.7 (−0.5) |
| 2,3-Dichlorophenol | −1.5 (+0.8) | −7.0 (+0.7) | −7.8 (+0.7) | |
| 2,4-Dichlorophenol | −1.9 (+0.4) | −7.4 (+0.3) | −8.4 (+0.1) | |
| 2,5-Dichlorophenol | −1.5 (+0.8) | −7.1 (+0.6) | −7.9 (+0.6) | |
| 2,6-Dichlorophenol | −3.5 (−1.2) | −9.0 (−1.3) | −10.1 (−1.6) | |
| 3,4-Dichlorophenol | −2.9 (−0.6) | −8.2 (−0.5) | −9.1 (−0.6) | |
| 3,5-Dichlorophenol | −2.7 (−0.4) | −8.0 (−0.3) | −8.8 (−0.3) | |
| 2,3,4-Trichlorophenol | −1.8 (+0.5) | −7.3 (+0.4) | −8.2 (+0.3) | |
| 2,3,5-Trichlorophenol | −1.6 (+0.7) | −7.1 (+0.6) | −7.9 (+0.6) | |
| 2,3,6-Trichlorophenol | −3.4 (−1.1) | −9.0 (−1.3) | −10.0 (−1.5) | |
| 2,4,5-Trichlorophenol | −2.0 (+0.3) | −7.5 (+0.2) | −8.4 (+0.1) | |
| 2,4,6-Trichlorophenol | −3.8 (−1.5) | −9.4 (−1.7) | −10.6 (−2.1) | |
| 3,4,5-Trichlorophenol | −3.0 (−0.7) | −8.4 (−0.7) | −9.3 (−0.8) | |
| 2,3,4,5-Tetrachlorophenol | −7.4 (+0.3) | −8.3 (+0.2) | ||
| 2,3,4,6-Tetrachlorophenol | −9.2 (−1.5) | −10.3 (−1.8) | ||
| 2,3,5,6-Tetrachlorophenol | −9.1 (−1.4) | −10.0 (−1.5) | ||
| Pentachlorophenol | −9.4 (−1.7) | −10.5 (−2.0) |