Quantitative Structure-Activity Relationships Study on the Rate Constants of Polychlorinated Dibenzo-p-Dioxins with OH Radical
Abstract
:1. Introduction
2. Results and Discussion
2.1. Reactions with OH Radicals
2.2. Relation between Rate Constants and the Configuration Parameters
2.2.1. kα, kβ and kγ with the Configuration Parameters
Compound | kα | kβ | kγ | Nα | Nβ | N1,9 | N2,8 | No | Nm | Np | N | EHOMO | ELUMO | ΔEHOMO-LUMO | D |
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
MCDDs | |||||||||||||||
1 | 1.35 × 10−13 | 9.15 × 10−12 | 7.40 × 10−12 | 1 | 0 | 1 | 0 | 0 | 0 | 0 | 1 | −0.247 | −0.003 | 0.245 | 1.63 |
2 | 3.18 × 10−13 | 1.69 × 10−11 | 1.12 × 10−11 | 0 | 1 | 0 | 1 | 0 | 0 | 0 | 1 | −0.246 | −0.003 | 0.243 | 2.07 |
DCDDs | |||||||||||||||
1,2 | 8.66 × 10−14 | 3.98 × 10−12 | 8.21 × 10−12 | 1 | 1 | 1 | 1 | 1 | 1 | 0 | 2 | −0.251 | −0.010 | 0.242 | 2.86 |
1,3 | 4.44 × 10−13 | 5.66 × 10−12 | 7.97 × 10−12 | 1 | 1 | 1 | 0 | 0 | 1 | 0 | 2 | −0.253 | −0.011 | 0.242 | 2.29 |
1,4 | 8.23 × 10−14 | 1.13 × 10−11 | 5.50 × 10−12 | 2 | 0 | 1 | 0 | 0 | 0 | 1 | 2 | −0.255 | −0.011 | 0.244 | 0.88 |
1,6 | 5.25 × 10−13 | 1.54 × 10−11 | 5.62 × 10−12 | 2 | 0 | 1 | 0 | 0 | 0 | 0 | 2 | −0.255 | −0.010 | 0.245 | 0.00 |
1,7 | 2.34 × 10−13 | 8.03 × 10−12 | 6.81 × 10−12 | 1 | 1 | 1 | 0 | 0 | 0 | 0 | 2 | −0.253 | −0.011 | 0.243 | 1.52 |
1,8 | 2.72 × 10−13 | 7.81 × 10−12 | 8.25 × 10−12 | 1 | 1 | 1 | 1 | 0 | 0 | 0 | 2 | −0.253 | −0.011 | 0.242 | 2.79 |
1,9 | 2.85 × 10−13 | 8.39 × 10−12 | 5.57 × 10−12 | 2 | 0 | 2 | 0 | 0 | 0 | 0 | 2 | −0.255 | −0.010 | 0.245 | 2.99 |
2,3 | 3.07 × 10−13 | 4.58 × 10−12 | 7.92 × 10−12 | 0 | 2 | 0 | 1 | 1 | 0 | 0 | 2 | −0.251 | −0.009 | 0.242 | 3.16 |
2,7 | 2.45 × 10−13 | 3.90 × 10−12 | 1.10 × 10−11 | 0 | 2 | 0 | 1 | 0 | 0 | 0 | 2 | −0.252 | −0.012 | 0.241 | 0.00 |
2,8 | 1.99 × 10−13 | 4.63 × 10−12 | 1.05 × 10−11 | 0 | 2 | 0 | 2 | 0 | 0 | 0 | 2 | −0.252 | −0.012 | 0.240 | 1.79 |
Tri-CDDs | |||||||||||||||
1,2,3 | 2.11 × 10−13 | 2.46 × 10−12 | 7.40 × 10−12 | 1 | 2 | 1 | 1 | 2 | 1 | 0 | 3 | −0.256 | −0.015 | 0.241 | 3.42 |
1,2,4 | 1.04 × 10−13 | 6.06 × 10−12 | 7.66 × 10−12 | 2 | 1 | 1 | 1 | 1 | 1 | 1 | 3 | −0.258 | −0.018 | 0.240 | 2.40 |
1,2,6 | 8.76 × 10−14 | 1.85 × 10−12 | 5.61 × 10−12 | 2 | 1 | 1 | 1 | 1 | 0 | 0 | 3 | −0.259 | −0.017 | 0.242 | 1.59 |
1,2,7 | 9.32 × 10−14 | 2.22 × 10−12 | 7.55 × 10−12 | 1 | 2 | 1 | 1 | 1 | 0 | 0 | 3 | −0.257 | −0.017 | 0.240 | 1.14 |
1,2,8 | 9.77 × 10−14 | 1.81 × 10−12 | 8.14 × 10−12 | 1 | 2 | 1 | 2 | 1 | 0 | 0 | 3 | −0.257 | −0.017 | 0.240 | 2.89 |
1,2,9 | 7.05 × 10−14 | 2.66 × 10−12 | 5.68 × 10−12 | 2 | 1 | 2 | 1 | 1 | 0 | 0 | 3 | −0.258 | −0.016 | 0.242 | 3.76 |
1,3,6 | 4.03 × 10−13 | 4.99 × 10−12 | 7.66 × 10−12 | 2 | 1 | 1 | 0 | 0 | 1 | 0 | 3 | −0.260 | −0.018 | 0.242 | 1.96 |
1,3,7 | 2.16 × 10−13 | 1.57 × 10−12 | 8.17 × 10−12 | 1 | 2 | 1 | 0 | 0 | 1 | 0 | 3 | −0.259 | −0.019 | 0.240 | 0.48 |
1,3,8 | 3.04 × 10−13 | 4.63 × 10−12 | 1.04 × 10−11 | 1 | 2 | 1 | 1 | 0 | 1 | 0 | 3 | −0.259 | −0.019 | 0.240 | 1.51 |
1,3,9 | 1.90 × 10−13 | 2.38 × 10−12 | 5.80 × 10−12 | 2 | 1 | 2 | 0 | 0 | 1 | 0 | 3 | −0.260 | −0.018 | 0.242 | 2.66 |
1,4,6 | 7.72 × 10−14 | 2.60 × 10−12 | 3.95 × 10−12 | 3 | 0 | 1 | 0 | 0 | 0 | 1 | 3 | −0.262 | −0.017 | 0.245 | 1.48 |
1,4,7 | 1.17 × 10−13 | 4.45 × 10−12 | 5.93 × 10−12 | 2 | 1 | 1 | 0 | 0 | 0 | 1 | 3 | −0.260 | −0.018 | 0.242 | 1.27 |
2,3,6 | 2.98 × 10−13 | 2.92 × 10−12 | 5.63 × 10−12 | 1 | 2 | 0 | 1 | 1 | 0 | 0 | 3 | −0.258 | −0.016 | 0.242 | 3.06 |
2,3,7 | 1.82 × 10−13 | 1.04 × 10−12 | 7.47 × 10−12 | 0 | 3 | 0 | 1 | 1 | 0 | 0 | 3 | −0.257 | −0.017 | 0.240 | 1.58 |
Compound | kα | kβ | kγ | Nα | Nβ | N1,9 | N2,8 | No | Nm | Np | N | EHOMO | ELUMO | ΔEHOMO-LUMO | D |
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
TCDDs | |||||||||||||||
1,2,3,4 | 6.62 × 10−14 | 2.07 × 10−12 | 7.06 × 10−12 | 2 | 2 | 1 | 1 | 3 | 2 | 1 | 4 | −0.260 | −0.022 | 0.239 | 3.30 |
1,2,3,6 | 1.91 × 10−13 | 1.35 × 10−12 | 5.38 × 10−12 | 2 | 2 | 1 | 1 | 2 | 1 | 0 | 4 | −0.263 | −0.022 | 0.241 | 2.77 |
1,2,3,7 | 2.00 × 10−13 | 1.34 × 10−12 | 7.56 × 10−12 | 1 | 3 | 1 | 1 | 2 | 1 | 0 | 4 | −0.261 | −0.023 | 0.239 | 1.42 |
1,2,3,8 | 2.39 × 10−13 | 7.45 × 10−13 | 7.97 × 10−12 | 1 | 3 | 1 | 2 | 2 | 1 | 0 | 4 | −0.261 | −0.023 | 0.239 | 2.40 |
1,2,3,9 | 1.34 × 10−13 | 1.70 × 10−12 | 5.23 × 10−12 | 2 | 2 | 2 | 1 | 2 | 1 | 0 | 4 | −0.262 | −0.022 | 0.241 | 3.71 |
1,2,4,6 | 4.89 × 10−14 | 1.79 × 10−12 | 4.88 × 10−12 | 3 | 1 | 1 | 1 | 1 | 1 | 1 | 4 | −0.265 | −0.024 | 0.241 | 2.05 |
1,2,4,7 | 6.42 × 10−14 | 1.09 × 10−12 | 7.42 × 10−12 | 2 | 2 | 1 | 1 | 1 | 1 | 1 | 4 | −0.263 | −0.025 | 0.239 | 0.61 |
1,2,4,8 | 7.46 × 10−14 | 2.02 × 10−12 | 7.10 × 10−12 | 2 | 2 | 1 | 2 | 1 | 1 | 1 | 4 | −0.263 | −0.025 | 0.238 | 1.48 |
1,2,4,9 | 3.81 × 10−14 | 2.16 × 10−12 | 4.97 × 10−12 | 3 | 1 | 2 | 1 | 1 | 1 | 1 | 4 | −0.265 | −0.024 | 0.241 | 2.68 |
1,2,6,7 | 6.42 × 10−14 | 1.18 × 10−12 | 6.06 × 10−12 | 2 | 2 | 1 | 1 | 2 | 0 | 0 | 4 | −0.262 | −0.023 | 0.239 | 0.00 |
1,2,6,8 | 1.47 × 10−13 | 2.36 × 10−12 | 8.51 × 10−12 | 2 | 2 | 1 | 2 | 1 | 1 | 0 | 4 | −0.263 | −0.024 | 0.239 | 1.41 |
1,2,6,9 | 5.65 × 10−14 | 1.92 × 10−12 | 4.16 × 10−12 | 3 | 1 | 2 | 1 | 1 | 0 | 1 | 4 | −0.265 | −0.023 | 0.241 | 2.17 |
1,2,7,8 | 1.45 × 10−13 | 8.84 × 10−13 | 6.35 × 10−12 | 1 | 3 | 1 | 2 | 2 | 0 | 0 | 4 | −0.261 | −0.023 | 0.239 | 2.28 |
1,2,7,9 | 1.93 × 10−13 | 1.51 × 10−12 | 8.04 × 10−12 | 2 | 2 | 2 | 1 | 1 | 1 | 0 | 4 | −0.263 | −0.024 | 0.240 | 2.49 |
1,2,8,9 | 6.79 × 10−14 | 1.53 × 10−12 | 7.22 × 10−12 | 2 | 2 | 2 | 2 | 2 | 0 | 0 | 4 | −0.261 | −0.023 | 0.239 | 3.88 |
1,3,6,8 | 4.41 × 10−13 | 2.69 × 10−12 | 9.96 × 10−12 | 2 | 2 | 1 | 1 | 0 | 2 | 0 | 4 | −0.265 | −0.025 | 0.240 | 0.00 |
1,3,6,9 | 2.71 × 10−13 | 2.35 × 10−12 | 5.68 × 10−12 | 3 | 1 | 2 | 0 | 0 | 1 | 1 | 4 | −0.267 | −0.025 | 0.242 | 1.39 |
1,3,7,8 | 2.25 × 10−13 | 1.38 × 10−12 | 6.97 × 10−12 | 1 | 3 | 1 | 1 | 1 | 1 | 0 | 4 | −0.263 | −0.024 | 0.239 | 1.08 |
1,3,7,9 | 2.57 × 10−13 | 2.41 × 10−12 | 7.57 × 10−12 | 2 | 2 | 2 | 0 | 0 | 2 | 0 | 4 | −0.265 | −0.025 | 0.240 | 1.08 |
1,4,6,9 | 3.93 × 10−16 | 3.70 × 10−12 | 3.20 × 10−12 | 4 | 0 | 2 | 0 | 0 | 0 | 2 | 4 | −0.269 | −0.024 | 0.244 | 0.00 |
1,4,7,8 | 1.24 × 10−13 | 1.35 × 10−12 | 4.06 × 10−12 | 2 | 2 | 1 | 1 | 1 | 0 | 1 | 4 | −0.264 | −0.024 | 0.241 | 2.21 |
2,3,7,8 | 1.72 × 10−13 | 1.35 × 10−15 | 5.20 × 10−12 | 0 | 4 | 0 | 2 | 2 | 0 | 0 | 4 | −0.261 | −0.022 | 0.239 | 0.00 |
Compound | kα | kβ | kγ | Nα | Nβ | N1,9 | N2,8 | No | Nm | Np | N | EHOMO | ELUMO | ΔEHOMO-LUMO | D |
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Penta-CDDs | |||||||||||||||
1,2,3,4,6 | 4.48 × 10−14 | 9.83 × 10−13 | 5.07 × 10−12 | 3 | 2 | 1 | 1 | 3 | 2 | 1 | 5 | −0.267 | −0.028 | 0.240 | 3.14 |
1,2,3,4,7 | 4.09 × 10−14 | 6.84 × 10−13 | 7.14 × 10−12 | 2 | 3 | 1 | 1 | 3 | 2 | 1 | 5 | −0.265 | −0.028 | 0.237 | 1.70 |
1,2,3,6,7 | 1.34 × 10−13 | 2.34 × 10−13 | 6.10 × 10−12 | 2 | 3 | 1 | 1 | 3 | 1 | 0 | 5 | −0.266 | −0.028 | 0.238 | 1.51 |
1,2,3,6,8 | 2.05 × 10−13 | 1.09 × 10−12 | 7.71 × 10−12 | 2 | 3 | 1 | 2 | 2 | 2 | 0 | 5 | −0.267 | −0.029 | 0.238 | 1.12 |
1,2,3,6,9 | 1.10 × 10−13 | 6.93 × 10−13 | 4.24 × 10−12 | 3 | 2 | 2 | 1 | 2 | 1 | 1 | 5 | −0.269 | −0.028 | 0.240 | 2.49 |
1,2,3,7,8 | 1.49 × 10−13 | 1.24 × 10−15 | 5.21 × 10−12 | 1 | 4 | 1 | 2 | 3 | 1 | 0 | 5 | −0.265 | −0.028 | 0.237 | 1.06 |
1,2,3,7,9 | 1.66 × 10−13 | 7.56 × 10−13 | 6.46 × 10−12 | 2 | 3 | 2 | 1 | 2 | 2 | 0 | 5 | −0.267 | −0.029 | 0.238 | 1.84 |
1,2,3,8,9 | 1.01 × 10−13 | 5.26 × 10−13 | 6.51 × 10−12 | 2 | 3 | 2 | 2 | 3 | 1 | 0 | 5 | −0.266 | −0.028 | 0.238 | 3.18 |
1,2,4,6,7 | 3.66 × 10−14 | 1.98 × 10−12 | 5.72 × 10−12 | 3 | 2 | 1 | 1 | 2 | 1 | 1 | 5 | −0.268 | −0.030 | 0.239 | 1.39 |
1,2,4,6,8 | 2.38 × 10−13 | 2.50 × 10−12 | 1.17 × 10−11 | 3 | 2 | 1 | 2 | 1 | 2 | 1 | 5 | −0.267 | −0.029 | 0.238 | 1.12 |
1,2,4,6,9 | 7.33 × 10−16 | 1.56 × 10−12 | 4.79 × 10−12 | 4 | 1 | 2 | 1 | 1 | 1 | 2 | 5 | −0.271 | −0.030 | 0.241 | 1.51 |
1,2,4,7,8 | 7.27 × 10−14 | 5.78 × 10−13 | 4.89 × 10−12 | 2 | 3 | 1 | 2 | 2 | 1 | 1 | 5 | −0.267 | −0.030 | 0.238 | 0.93 |
1,2,4,7,9 | 8.16 × 10−14 | 2.05 × 10−12 | 7.50 × 10−12 | 3 | 2 | 2 | 1 | 1 | 2 | 1 | 5 | −0.270 | −0.031 | 0.239 | 1.02 |
1,2,4,8,9 | 3.71 × 10−14 | 1.12 × 10−12 | 6.03 × 10−12 | 3 | 2 | 2 | 2 | 2 | 1 | 1 | 5 | −0.268 | −0.030 | 0.238 | 2.41 |
Hexa-CDDs | |||||||||||||||
1,2,3,4,6,7 | 1.60 × 10−14 | 2.54 × 10−13 | 6.16 × 10−12 | 3 | 3 | 1 | 1 | 4 | 2 | 1 | 6 | −0.270 | −0.033 | 0.237 | 2.26 |
1,2,3,4,6,8 | 1.10 × 10−13 | 8.46 × 10−13 | 7.87 × 10−12 | 3 | 3 | 1 | 2 | 3 | 3 | 1 | 6 | −0.271 | −0.034 | 0.237 | 1.19 |
1,2,3,4,6,9 | 7.74 × 10−16 | 7.82 × 10−13 | 4.45 × 10−12 | 4 | 2 | 2 | 1 | 3 | 2 | 2 | 6 | −0.273 | −0.034 | 0.239 | 2.36 |
1,2,3,4,7,8 | 6.63 × 10−14 | 9.51 × 10−16 | 5.04 × 10−12 | 2 | 4 | 1 | 2 | 4 | 2 | 1 | 6 | −0.269 | −0.033 | 0.236 | 0.19 |
1,2,3,6,7,8 | 2.56 × 10−13 | 1.15 × 10−15 | 6.27 × 10−12 | 2 | 4 | 1 | 2 | 4 | 2 | 0 | 6 | −0.270 | −0.033 | 0.237 | 0.00 |
1,2,3,6,7,9 | 1.07 × 10−13 | 6.23 × 10−13 | 6.05 × 10−12 | 3 | 3 | 2 | 1 | 3 | 2 | 1 | 6 | −0.272 | −0.034 | 0.237 | 0.97 |
1,2,3,6,8,9 | 1.20 × 10−13 | 5.56 × 10−13 | 6.32 × 10−12 | 3 | 3 | 2 | 2 | 3 | 2 | 1 | 6 | −0.272 | −0.034 | 0.237 | 1.71 |
1,2,3,7,8,9 | 1.46 × 10−13 | 1.13 × 10−15 | 6.19 × 10−12 | 2 | 4 | 2 | 2 | 4 | 2 | 0 | 6 | −0.269 | −0.033 | 0.237 | 2.01 |
1,2,4,6,7,9 | 6.30 × 10−16 | 6.19 × 10−13 | 6.07 × 10−12 | 4 | 2 | 2 | 1 | 2 | 2 | 2 | 6 | −0.274 | −0.036 | 0.238 | 0.00 |
1,2,4,6,8,9 | 6.55 × 10−16 | 1.22 × 10−12 | 5.86 × 10−12 | 4 | 2 | 2 | 2 | 2 | 2 | 2 | 6 | −0.274 | −0.036 | 0.238 | 1.02 |
Hepta-CDDs | |||||||||||||||
1,2,3,4,6,7,8 | 7.21 × 10−14 | 9.28 × 10−16 | 5.71 × 10−12 | 3 | 4 | 1 | 2 | 5 | 3 | 1 | 7 | −0.273 | −0.038 | 0.236 | 0.95 |
1,2,3,4,6,7,9 | 6.81 × 10−16 | 4.15 × 10−13 | 5.41 × 10−12 | 4 | 3 | 2 | 1 | 4 | 3 | 2 | 7 | −0.276 | −0.039 | 0.237 | 1.06 |
OCDD | |||||||||||||||
1,2,3,4,6,7,8,9 | 7.95 × 10−16 | 7.51 × 10−16 | 5.98 × 10−12 | 4 | 4 | 2 | 2 | 6 | 4 | 2 | 8 | −0.277 | −0.043 | 0.235 | 0.00 |
2.2.2. The Total Rate Constant kOH with the Configuration Parameters
3. Computational Methods
3.1. Geometry Optimization
3.2. Kinetic Calculation
3.3. Quantitative Structure–Activity Relationship
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interests
References
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Qi, C.; Zhang, C.; Sun, X. Quantitative Structure-Activity Relationships Study on the Rate Constants of Polychlorinated Dibenzo-p-Dioxins with OH Radical. Int. J. Mol. Sci. 2015, 16, 18812-18824. https://doi.org/10.3390/ijms160818812
Qi C, Zhang C, Sun X. Quantitative Structure-Activity Relationships Study on the Rate Constants of Polychlorinated Dibenzo-p-Dioxins with OH Radical. International Journal of Molecular Sciences. 2015; 16(8):18812-18824. https://doi.org/10.3390/ijms160818812
Chicago/Turabian StyleQi, Chuansong, Chenxi Zhang, and Xiaomin Sun. 2015. "Quantitative Structure-Activity Relationships Study on the Rate Constants of Polychlorinated Dibenzo-p-Dioxins with OH Radical" International Journal of Molecular Sciences 16, no. 8: 18812-18824. https://doi.org/10.3390/ijms160818812