Relationship between gas chromatographic retention indices and molecular connectivity indices of chlorinated pesticides and structurally related compounds

Heinzen, Vilma Edite Fonseca; Yunes, Rosendo A.

doi:10.1016/0021-9673(92)85054-w

Cited by 11 publications

(4 citation statements)

References 16 publications

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“…The molecular connectivity indices of different orders (Xi and Xi v ) (Kier andHall, 1976, 1986;Yunes, 1992, 1993), electrotopological-state indices (Si) Georgakopoulos et al, 1991;Heinzen and Yunes, 1996;Heinzen et al, 1999), topological state indices (Ti) (Hall and Kier, 1990), and indices of molecular shape, kappa values ( i Κ) (Kier, 1987;Heinzen and Yunes, 1996), were calculated using the computational program Molconn-X, developed by . These indices express, in a general way, the topological environment of each atom, the linearity and the branching of the molecule, the presence of heteroatoms, the charge distribution, and the electronic effects in molecules (Kier andHall, 1976, 1986;Georgakopoulos et al, 1991;Kier, 1987;Heinzen and Yunes, 1992, 1996Heinzen et al, 1999).…”

Section: Methodsmentioning

confidence: 99%

Quantitative Structure−Odor Relationships of Aliphatic Esters Using Topological Indices

Amboni

et al. 2000

J. Agric. Food Chem.

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Quantitative structure-activity relationships (QSAR) were used in this study to relate the structural parameters (electronic, topological, etc.) to the odor of 27 aliphatic esters previously evaluated by Rossiter. Rossiter used the Hansch approach, principal component analysis and comparative molecular field analysis (CoMFA) to predict the odor of these esters. Different structural parameters were selected, such as topological, physicochemical, and quantum-chemical indices, to find an equation to predict the molecular factors that determine the fruit odor of these compounds and to compare such results with those obtained by Rossiter. Two significant correlation equations were obtained with the following molecular descriptors: one with the electrotopological-state index related to the carbon atom of the carbonyl group (S(C)(=)(O)), the Kappa index ((2)Kappa), and the topological-state index related to the oxygen on the alcoholic side of the molecule (T(-)(O)(-)), and the other with (2)Kappa, S(C)(=)(O), and the energy of the highest occupied molecular orbital (E(HOMO)). The model found had a good predictive ability as established by cross-validation r(2)(cv) values and thus can be used to help in the prediction of odor of similar compounds. This method is simplier than the methods used by Rossiter and represents a reliable QSAR alternative in predicting the fruit odor of such aliphatic esters.

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Section: Methodsmentioning

confidence: 99%

Quantitative Structure−Odor Relationships of Aliphatic Esters Using Topological Indices

Amboni

et al. 2000

J. Agric. Food Chem.

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“…To that end, the possibility of estimating σ from easily computable topological indices was studied. The utility of some very popular topological indices is incontestable as they have been successfully implemented in quantitative structure–property relationship and quantitative structure–activity relationship. − Their implementation can be done independently or within a set of molecular descriptors (topological, geometric, electronic,...) that are correlated to physicochemical properties through a multiple regression analysis. ,− …”

Section: Introductionmentioning

confidence: 99%

“…The last selected topological descriptor was the Randić index, , based on the adjacency matrix of the molecular graph. It was specifically designed to best characterize the molecular branching, and it was identified as a measure of the intermolecular accessibility. , All four selected topological indices have been successfully correlated to a large number of physical and chemical properties, such as the boiling and melting points, ,,,, thermodynamic parameters, ,− the retention time indices in chromatography, ,,, the ultrasonic sound velocity, the electron energy characteristics of infinite conjugated polymers, , toxicity analyses, the aqueous solubility of organic compounds, the van der Waals surfaces of alkanes, , and drug design and pharmaceutical properties . Of note, in a paper of 1989, Rouvray has already reported that molecular cross-sections can be modeled with topological indices.…”

Section: Introductionmentioning

confidence: 99%

Correlation of the Molecular Cross-Sectional Area of Organic Monofunctional Compounds with Topological Descriptors

Desmecht,

Dubois

2024

J. Chem. Inf. Model.

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The molecular cross-sectional area (σ) has proved to be an interesting molecular measure not only in the field of adsorption phenomena on solids but also in biochemistry, physiology, or surfactant chemistry. The existing methods to estimate the cross-sectional areas are either not readily applicable or can only be applied to a limited number of compounds. The aim of this work was to describe a method, as general as possible, quick and easy to perform. To that end, the molecular cross-sectional areas were correlated with topological indices. The Emmett− Brunauer formula was used to calculate the reference crosssectional areas (σ EB ) of 431 compounds. The correlations of the Wiener (W), hyper-Wiener (WW), Balaban (J), and Randić(χ) indices with σ EB were compared for n-alkanes as well as branched and cyclic alkanes. Only the Wiener and hyper-Wiener indices correlated well with σ EB , with the data being best fitted by power law regression curves. The lower degeneracy of the hyper-Wiener index did not translate into any significant gain of performance when correlated with σ EB . Following the parsimony principle, the less complex Wiener index was thus selected to correlate with the σ EB of compounds representing 31 other monofunctional and structural families. The integration of all the compound families into a single curve allowed a quick rough estimation of the crosssectional areas. The specific reference equations σ EB = qW p were determined for the 34 selected families, allowing the fast and reliable calculation of the cross-sectional area of any monofunctional compound.

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“…Using the QSRR approach, structural descriptors such as topological, geometric and electronic or physico-chemical descriptors can be proposed for molecules with similar structural features, and a subset of them can be selected in order to describe and predict the gas chromatographic retention indices 2 . Numerous authors have attempted to correlate and predict retention indices of a variety of compounds by use of molecular structural information or physico-chemical and quantum-chemical parameters [3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] .…”

Section: Introductionmentioning

confidence: 99%

Prediction of Gas Chromatographic Retention Indices of Coumarins

Soares¹,

Monachè²,

Heinzen³

et al. 1999

J. Braz. Chem. Soc.

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Relationship between gas chromatographic retention indices and molecular connectivity indices of chlorinated pesticides and structurally related compounds

Cited by 11 publications

References 16 publications

Quantitative Structure−Odor Relationships of Aliphatic Esters Using Topological Indices

Quantitative Structure−Odor Relationships of Aliphatic Esters Using Topological Indices

Correlation of the Molecular Cross-Sectional Area of Organic Monofunctional Compounds with Topological Descriptors

Prediction of Gas Chromatographic Retention Indices of Coumarins

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