The internal relation between quantum chemical descriptors and empirical constants of polychlorinated compounds

Jiangchi Fei, Qiming Mao, Lu Peng, Tiantian Ye, Yuan Yang*, Shuang Luo

*Corresponding author for this work

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaperJournal articleResearchpeer-review

11 Citations (Scopus)

Abstract

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.

Original languageEnglish
Article number2935
JournalMolecules
Volume23
Issue11
ISSN1420-3049
DOIs
Publication statusPublished - 10 Nov 2018

Keywords

  • Hammett constant
  • Meta-position
  • Prediction model
  • Quantum chemical descriptor

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