A conceptual DFT and information-theoretic approach towards QSPR modeling in polychlorobiphenyls

被引：0
作者：
Arpita Poddar
Ranita Pal
Chunying Rong
Pratim Kumar Chattaraj
机构：
[1] Indian Institute of Technology Kharagpur,Department of Chemistry
[2] Indian Institute of Technology Kharagpur,Advanced Technology Development Centre
[3] Hunan Normal University,College of Chemistry and Chemical Engineering
来源：
Journal of Mathematical Chemistry | 2023年 / 61卷
关键词：
Quantitative structure–property relationship; Conceptual density functional theory; Information theory; Multilinear regression;
D O I：
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中图分类号：
学科分类号：
摘要：
Quantitative structure–property relationship (QSPR) of various chlorine substituted biphenyl systems on the basis of linear and multi-linear regression (MLR) analysis is presented in this study. The determination of lipophilicity (log KOW) of the selected 133 polychlorobiphenyl (PCB) congeners is carried out taking the experimental log KOW as the dependent variable and the conceptual density functional theory (CDFT) and information theory (IT) based descriptors (global electrophilicity index (ω), its square term (ω2), and Shannon entropy (SS), GBP entropy (SGBP)) as independent variables. These are used to map the relationship between experimental log KOW and predicted log KOW. The best model is obtained using CDFT descriptor (ω) along with IT quantities (SS, SGBP) when combined linearly. The results show a very good coefficient of determination value (R2 = 0.9261) along with a high internal predicting ability (R2CV = 0.9208) which indicates the importance of the mentioned descriptors for the quantitative structure–property analysis of selected PCBs.
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页码：1143 / 1164
页数：21
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共 106 条
  • [1] Hansch C(1962)Correlation of biological activity of phenoxyacetic acids with Hammett substituent constants and partition coefficients Nature 194 178-180
  • [2] Maloney P(1964)p-σ-π Analysis. A method for the correlation of biological activity and chemical structure J. Am. Chem. Soc. 86 1616-1626
  • [3] Fujita T(1998)Quantitative structure–activity relationships of chemicals acting by non-polar narcosis—theoretical considerations Quant. Struct.-Act. Relat. 17 131-138
  • [4] Muir R(1997)Predicting modes of toxic action from chemical structure: acute toxicity in the fathead minnow ( Environ. Toxicol. Chem. 16 948-967
  • [5] Hansch C(2002)) Bioorg. Med. Chem. 10 1761-1766
  • [6] Fujita T(1996)Study on quantitative structure–toxicity relationships of benzene derivatives acting by narcosis Chem. Rev. 96 1027-1044
  • [7] Zhao YH(1935)Quantum-chemical descriptors in QSAR/QSPR studies Chem. Rev. 17 125-136
  • [8] Cronin MT(1937)Some relations between reaction rates and equilibrium constants J. Am. Chem. Soc. 59 96-103
  • [9] Dearden JC(2004)The effect of structure upon the reactions of organic compounds. Benzene derivatives Bioorg. Med. Chem. Lett. 12 5533-5543
  • [10] Russom CL(2004)Electrophilicity index as a possible descriptor of biological activity Curr. Sci. 86 535-122
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