Structure-retention relationship analysis for some mono- and polycyclic aromatic hydrocarbons in reversed-phase liquid chromatography using molecular connectivity

Wells, Martha J.M.; Clark, Charles R.; Patterson, R. M.

doi:10.1021/ac00121a008

Cited by 17 publications

(1 citation statement)

References 79 publications

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“…On the other hand, structure‐related molecular properties can be computed easily and simple functions of these descriptors can predict retention values despite the complexity of the phenomenon. Examples of descriptors employed in the QSRRs of PAHs are the number of carbon atoms, connectivity indices, molecular sizes, the moment of inertia, and the quadrupole moment together with the polarizability …”

Section: Introductionmentioning

confidence: 99%

Quantitative Structure–Retention Relationships for Polycyclic Aromatic Hydrocarbons and their Oligoalkynyl‐Substituted Derivatives

et al. 2017

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Reversed‐phase high‐performance liquid chromatography (RP‐HPLC) has been carried out for a series of unsubstituted polycyclic aromatic hydrocarbons (PAHs) and the corresponding ethynyl, 1,3‐butadiynyl, and 1,3,5‐hexatriynyl derivatives. Theoretical values of the isotropic polarizability and several polarity descriptors have been computed for each compound by using semiempirical models and density functional theory (DFT), with the aim of evaluating linear functions as quantitative structure–retention relationships (QSRRs). The polarity has been described by using either the permanent electric dipole moment, the subpolarity, or a topological electronic index. Three types of partial atomic charges have been used to calculate the subpolarity and a topological index. The choice of the theoretical model, of the polarity descriptor, and of the partial atomic charges is discussed and the resulting QSRRs are compared. Calculating the retention times from the polarizability and the topological electronic index (AM1, PM3, or DFT‐B3LYP/6–31+G(d,p)) gives the best agreement with the experimental values.

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Section: Introductionmentioning

confidence: 99%

Quantitative Structure–Retention Relationships for Polycyclic Aromatic Hydrocarbons and their Oligoalkynyl‐Substituted Derivatives

et al. 2017

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Studies of Performance of Graph Theoretical Indices in QSAR Analysis

Ośamiałowski¹,

Kaliszan²

1991

Quant. Struct.‐Act. Relat.

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Comparative studies of performance in exemplary QSAR of the most commonly used structural descriptors derived from molecular graphs were performed. Three diverse series of test compounds were selected for which various property measures existed. One group of compounds were polychlorinated dibenzofurans of determined gas chromatographic retention indices. The second group comprised isomers of general formula C4H8O of known boiling points, refractivity indices and densities. Third set of agents consisted of 2‐substituted isonicotinic acid hydrazides of determined antibacterial activity. The following graph theoretical indices were considered: the Kier and Hall [22] generalized molecular connectivity indices, the Balaban distance sum connectivity index calculated after Barysz et al. [23], the indices of molecular shape of Kier [24], the information indices of neighbourhood symmetry of Sarkar et al. [25] and of Basak et al. [26]. Auxiliary structural parameters, e.g., molecular surface area, were also employed. Significant correlation with molecular mass and intercorrelations among the graph theoretical indices were observed excepting the group of information content indices. For the compounds and properties studied the graph theoretical indices considered appeared unable to provide a size‐independent, meaningful input to property description.

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Calculation of retention indices by molecular topology

Sekušak

Sabljić

1993

Journal of Chromatography A

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Structure-retention relationship analysis for some mono- and polycyclic aromatic hydrocarbons in reversed-phase liquid chromatography using molecular connectivity

Cited by 17 publications

References 79 publications

Quantitative Structure–Retention Relationships for Polycyclic Aromatic Hydrocarbons and their Oligoalkynyl‐Substituted Derivatives

Quantitative Structure–Retention Relationships for Polycyclic Aromatic Hydrocarbons and their Oligoalkynyl‐Substituted Derivatives

Studies of Performance of Graph Theoretical Indices in QSAR Analysis

Calculation of retention indices by molecular topology

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