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Molecules 2018, 23(11), 2935;

The Internal Relation between Quantum Chemical Descriptors and Empirical Constants of Polychlorinated Compounds

Institute of Environmental Engineering, School of Metallurgy and Environment, Central South University, Changsha 410083, China
College of Resources and Environment, Hunan Agricultural University, Changsha 410128, China
College of Biology and Environmental Sciences, Jishou University, Jishou 416000, China
South China Institute of Environmental Sciences, Ministry of Environmental Protection, Guangzhou 510655, China
Authors to whom correspondence should be addressed.
Academic Editor: Kok Hwa Lim
Received: 11 October 2018 / Revised: 6 November 2018 / Accepted: 6 November 2018 / Published: 10 November 2018
(This article belongs to the Special Issue QSAR and QSPR: Recent Developments and Applications)
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Quantum chemical descriptors and empirical parameters are two different types of chemical parameters that play the fundamental roles in chemical reactivity and model development. However, previous studies have lacked detail regarding the relationship between quantum chemical descriptors and empirical constants. We selected polychlorinated biphenyls (PCBs) as an object to investigate the intrinsic correlation between 16 quantum chemical descriptors and Hammett constants. The results exhibited extremely high linearity for σ o ,   m ,   p + with Qxx/yy/zz, α and EHOMO based on the meta-position grouping. Polychlorinated dibenzodioxins (PCDDs) and polychlorinated naphthalenes (PCNs) congeners, as two independent compounds, validated the reliability of the relationship. The meta-substituent grouping method between σ o ,   m ,   p + and α was successfully used to predict the rate constant (k) for OH oxidation of PCBs, as well as the octanol/water partition coefficient (logKOW) and aqueous solubility (−logSW) of PCDDs, and exhibited excellent agreement with experimental measurements. Revealing the intrinsic correlation underlying the empirical constant and quantum chemical descriptors can develop simpler and higher efficient model application in predicting the environmental behavior and chemical properties of compounds. View Full-Text
Keywords: quantum chemical descriptor; Hammett constant; meta-position; prediction model quantum chemical descriptor; Hammett constant; meta-position; prediction model

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Fei, J.; Mao, Q.; Peng, L.; Ye, T.; Yang, Y.; Luo, S. The Internal Relation between Quantum Chemical Descriptors and Empirical Constants of Polychlorinated Compounds. Molecules 2018, 23, 2935.

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