QSPR study of polychlorinated diphenyl ethers by molecular electronegativity distance vector (MEDV-4)

Sun, Lili; Zhou, Liping; Yu, Yu; Lan, Yukun; Li, Zhiliang

doi:10.1016/j.chemosphere.2006.07.013

Cited by 12 publications

(12 citation statements)

References 15 publications

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“…These ten elements combine atomic attributes (both the chemical element type and the chemical bond type of each atom), bond length, relative distance between atoms, and their relative electronegativities. The relative electronegativity of a nonhydrogen atom is defined as the ratio of Pauling's electronegativity of the non-hydrogen atom to Pauling's electronegativity of a carbon atom, and the relative distance or relative bond length of a chemical bond is defined as the ratio of the length of this bond to the bond length of the C-C bond (Liu et al, 2002;Sun et al, 2007).…”

Section: Quantum-chemical Descriptorsmentioning

confidence: 99%

“…Several MCI ( 0 χ v , 1 χ , 1 χ v , χ , 3 χ v , 3 χ v pc , 5 χ v , 6 χ v c , or 6 χ v pc ) were used to predict the S W of 50 alcohols, 14 derivates of benzanilides, and miscellaneous compounds (Dai et al, 1998;Gerstl and Helling, 1987;Nirmalakhandan and Speece, 1988a): the best correlations were obtained for alcohols (r 2 = 0.961) and the worst for pesticides (r 2 = 0.389; Table S3). The S W of 107 PCDE was correlated to six quantum molecular electronegativity-distance vectors (M 11 , M 12 , M 13 , M 22 , M 23 , M 33 ; Sun et al, 2007). The combination of the polarizability α and the total energy TE was found useful to estimate the S W of 20 substituted phenols (r 2 = 0.980; Xie et al, 2008), and of 107 PCDE (r 2 = 0.956; Yang et al, 2003).…”

Section: Water Solubilitymentioning

confidence: 99%

See 1 more Smart Citation

Prediction of the Fate of Organic Compounds in the Environment From Their Molecular Properties: A Review

Mamy¹,

Patureau²,

Barriuso³

et al. 2014

Critical Reviews in Environmental Science and Technology

117

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A comprehensive review of quantitative structure-activity relationships (QSAR) allowing the prediction of the fate of organic compounds in the environment from their molecular properties was done. The considered processes were water dissolution, dissociation, volatilization, retention on soils and sediments (mainly adsorption and desorption), degradation (biotic and abiotic), and absorption by plants. A total of 790 equations involving 686 structural molecular descriptors are reported to estimate 90 environmental parameters related to these processes. A significant number of equations was found for dissociation process (pKa), water dissolution or hydrophobic behavior (especially through the KOW parameter), adsorption to soils and biodegradation. A lack of QSAR was observed to estimate desorption or potential of transfer to water. Among the 686 molecular descriptors, five were found to be dominant in the 790 collected equations and the most generic ones: four quantum-chemical descriptors, the energy of the highest occupied molecular orbital (EHOMO) and the energy of the lowest unoccupied molecular orbital (ELUMO), polarizability (α) and dipole moment (μ), and one constitutional descriptor, the molecular weight. Keeping in mind that the combination of descriptors belonging to different categories (constitutional, topological, quantum-chemical) led to improve QSAR performances, these descriptors should be considered for the development of new QSAR, for further predictions of environmental parameters. This review also allows finding of the relevant QSAR equations to predict the fate of a wide diversity of compounds in the environment.

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Section: Quantum-chemical Descriptorsmentioning

confidence: 99%

Section: Water Solubilitymentioning

confidence: 99%

Prediction of the Fate of Organic Compounds in the Environment From Their Molecular Properties: A Review

Mamy¹,

Patureau²,

Barriuso³

et al. 2014

Critical Reviews in Environmental Science and Technology

117

View full text Add to dashboard Cite

show abstract

“…In general, the interaction increases with the increment of the electro negativities and the decrement of the relative distance. In this report, we learn from the literature [6][7][8] to characterize the impact of the properties of molecular influenced by the vertices' interaction. The interaction from four types of vertexes can be grouped in ten elements, M 11 In the formula, n or l represents the types of vertexes i and j, i or j is an atom of vertexe in the molecular; Z i and Z j are the electro-negativities of atoms i and j relative to atom C (For example, the atoms of oxygen relative electro-negativity is 3.44/2.55 = 1.3490); r ij represents the relative distance between the ith vertex and the jth vertex (viz.…”

Section: Asian Journal Of Chemistry Asian Journal Of Chemistrymentioning

confidence: 99%

Studies on Quantitative Structure-Toxicity Relationship of Alcohols, Phenols, Ethers, Ketones and Esters

Lan¹,

Liu²,

Yu³

et al. 2014

Asian J. Chem.

Self Cite

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In order to find out the quantitative relationship between toxicity and structures of alcohols, phenols, ethers, ketones, esters, some structures of compounds were characterized by the values of molecular vertexes and their interaction. Two models of the quantitative structure-toxicity relationship (QSTR) were established by the methods multiple linear regression (MLR) and stepwise regression (SMR). A comparison of two models indicated that the model 2 (M2) showed better simulation results and the multiple correlation coefficient (R) was 0.952 and the value of standard deviation (SD) was 0.325. Jacknife method used for testing its stability indicated that the regression model 2 had an acceptable stability and a good predictive ability. In addition, the model was tested by the cross-validation with the leaveone-out (LOO) procedure. And the multiple correlation coefficient in cross-validation (RCV) was 0.927 and the value of standard deviation (SDCV) was 0.396, which showed the stability and predictive ability of the model were desirable.

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“…We took 38 benzene halides as the samples of this study and their lgKow listed in Table 1 were taken from the literature [4]. As for the QSPR research, our laboratory has developed a molecular structural characterization method called the molecular electronegativity-distance vector (MEDV) [5][6][7][8]. Based on the MEDV, the main aim of this study was to develop another molecular structural characterization method called the molecular vertex distance index (MVDI).…”

mentioning

confidence: 99%

“…where k or l represent the atomic types of atoms i and j; i or j is the code of an atom in the molecular skeleton graph; in the MEDV [5][6][7][8], Z i and Z j are the relative electronegativities of atoms i and j to atom C. But in this paper, Z i and Z j are the characteristic values of atoms i and j; d ij represents the relative distance between the ith and jth atoms (viz. sum of the experienced shortest path with respect to the relative C-C single bond length).…”

mentioning

confidence: 99%

Study on octanol-water partition coefficients of benzene halides by molecular vertex distance index

Liu

Lei

et al. 2011

J Struct Chem

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A new method of molecular structural characterization (MSC) called the molecular vertex distance index (MVDI) is constructed and used to describe the structures of benzene halides. Two quantitative structureproperty relationship (QSPR) models of octanol-water partition coefficients (lgKow) are obtained through multiple linear regression (MLR) and partial least squares regression (PLSR). The estimation stability and generalization ability of the models are analyzed by both internal and external validations. The results show that the models constructed in this work can provide satisfactory estimation stability and favorable predictive ability.The hydrophobic constant of organic compounds plays very important role in the environmental risk assessment and it is directly related to the migration and distribution of pollutants in the atmosphere, water, sediments, soil, and other environmental media as well as the organisms. The octanol-water partition coefficient (lgKow) is the most common form of the hydrophobic constant of organic compounds. The construction of a quantitative structure-property relationship (QSPR) requires the structural descriptors of related chemical compounds. Much meaningful work on QSPR has been done for a long time [1-3]. We took 38 benzene halides as the samples of this study and their lgKow listed in Table 1 were taken from the literature [4]. As for the QSPR research, our laboratory has developed a molecular structural characterization method called the molecular electronegativity-distance vector (MEDV) [5][6][7][8]. Based on the MEDV, the main aim of this study was to develop another molecular structural characterization method called the molecular vertex distance index (MVDI). A useful QSPR model of lgKow of benzene halides was also established in this work.Principles and methods. The property of an organic compound is directly related to the molecular structure. The octanol-water partition coefficient of organic matter is usually affected by the molecular size, flexibility and polarity, the hydrogen bonding between the molecules and so forth. For the molecular matrix skeleton, each non-hydrogen atom is a molecular vertex. The vertex is the basic unit of a molecule, so the external property of a compound can be reflected from the level of its vertices. Hence, the characteristic value of the vertex should be defined firstly for the correlative index. This definition is not a definite restriction and its purpose is to correlate the defined characteristic value with the practical problems of the research. The characteristic value of the vertex should exhibit the atomic structure and its surrounding environment. Without regard to non-framework hydrogen atoms, these vertex atoms were classified as four atomic types according to the atom number of each atom connecting to through some chemical bond/bonds. If an atom is linked to k

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QSPR study of polychlorinated diphenyl ethers by molecular electronegativity distance vector (MEDV-4)

Cited by 12 publications

References 15 publications

Prediction of the Fate of Organic Compounds in the Environment From Their Molecular Properties: A Review

Prediction of the Fate of Organic Compounds in the Environment From Their Molecular Properties: A Review

Studies on Quantitative Structure-Toxicity Relationship of Alcohols, Phenols, Ethers, Ketones and Esters

Study on octanol-water partition coefficients of benzene halides by molecular vertex distance index

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