Insights into the Retention Mechanisms on Perfluorohexylpropylsiloxane-Bonded (Fluophase-RP) and Octadecylsiloxane-Bonded (Betasil C18) Stationary Phases Based on the Same Silica Substrate in RP-LC

Poole, Colin F.; Ahmed, Hamid; Kiridena, Waruna; DeKay, C.; Koziol, Wladyslaw W.

doi:10.1365/s10337-006-0131-4

Cited by 29 publications

(9 citation statements)

References 25 publications

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“…Endo and Schmidt further pointed out that donor-dependency of H-bond basicity might pose another problem for compounds containing certain functional groups (alkyl ethers, nitroalkanes, methyl-substituted anilines, etc.). Poole et al discuss increased retention of weak bases due to ion-exchange interactions with the stationary phase in RP systems as a further confounding factor. However, although the compounds in our data set contain a large variety and combination of functional groups, no clear trends toward higher inconsistencies for compounds containing certain functional groups could be recognized.…”

Section: Resultsmentioning

confidence: 99%

Experimental Determination of LSER Parameters for a Set of 76 Diverse Pesticides and Pharmaceuticals

Tülp

Goss

Schwarzenbach

et al. 2008

Environ. Sci. Technol.

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Linear solvation energy relationships (LSERs) have more recently been proposed as the method of choice to describe and/or predict the partitioning behavior of neutral organic compounds over a large range of environmental matrices and for a broad variety of compounds in a consistent manner. However, when dealing with more complex, polar compounds with multiple functional groups, it has also been noted that there is a severe lack of substance descriptors quantifying the different intermolecular interactions that these compounds may undergo. In this study, we used a system of eight reversed phase, normal phase, and hydrophilic interaction HPLC systems to determine the substance descriptors for H-bond donor (A) and acceptor (B) interactions and for polarizability and dipolarity (S) for a set of 76 complex compounds containing multiple functional groups, comprising mainly pesticides and some pharmaceuticals. The obtained substance descriptors for most compounds are unique in that values of A, S, and B are high and lie at the very upper end of the numerical range of currently known substance descriptors. The substance descriptors have been cross-compared against literature values of the octanol-water (Kow) and air-water (Kaw) partition coefficients and against a set of heptan-methanol partition coefficients (Khm) experimentally determined with a consistent methodology herein. The comparison confirmed plausibility of the substance descriptors of all except six tested compounds. The newly determined substance descriptors promise to be highly valuable in chemicalfate modeling, allowing, in conjunction with available phase descriptors, for a better representation of partitioning of polar compounds in those models. The results also reveal a systematic deviation of the log Kow values predicted with our substance descriptors from the literature values. The deviation points toward a possible problem when existing LSER equations are applied to polar, multifunctional compounds with high values of A, S, and B. Hence, the substance descriptors determined herein should also be helpful in revisiting the validity of existing LSERs for complex, polar compounds.

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Section: Resultsmentioning

confidence: 99%

Experimental Determination of LSER Parameters for a Set of 76 Diverse Pesticides and Pharmaceuticals

Tülp

Goss

Schwarzenbach

et al. 2008

Environ. Sci. Technol.

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“…It has been demonstrated that perfluoroalkyl‐modified stationary LC columns can be used to separate analytes not only by fluorophilicity, but also by secondary separation effects such as electrostaticity derived from the significant number of silanol residues in silica‐gel‐based fluorinated phases . The separation can also be controlled by using a mobile phase consisting of a mixture of fluorophilic solvents, organic solvents, and water containing certain acids or bases, and this method has also been used to separate positional isomers . We found in this study that our optimized LC conditions could successfully separate and selectively retain the derivatives of oligosaccharide isomers on the fluorous LC column.…”

Section: Structures Of Sialyl Oligosaccharides Used In This Studymentioning

confidence: 85%

Liquid chromatography/tandem mass spectrometry with fluorous derivatization method for selective analysis of sialyl oligosaccharides

Sakaguchi¹,

Hayama

Yoshida

et al. 2014

Rapid Comm Mass Spectrometry

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“…Many studies on the separation mechanism in LC with a fluorocarbon stationary phase have revealed that “secondary effects”, e.g., absorption to silanol residue on the particulate, and fluorophilicity affect the retention of analytes. − Therefore, LC columns with fluorocarbon stationary phases have been used to separate highly hydrophobic compounds − and structural isomers ,,− that are difficult to separate with conventional RP columns. Furthermore, drug analogues containing some trifluoromethyl structure, a C 1 fluorous unit, have been successfully determined by LC separation using a fluorous-phase column. , Because the fluorous stationary phase can retain fluorous compounds effectively, many examinations based on fluorous interaction have been conducted to collect or remove fluorous compounds ,,− and to investigate the specific separation mechanisms. − , However, to the best of our knowledge, there are no reports on quantitative analysis of fluorous-labeled compounds using a fluorous-phase LC column.…”

mentioning

confidence: 99%

Separation-Oriented Derivatization of Native Fluorescent Compounds through Fluorous Labeling Followed by Liquid Chromatography with Fluorous-Phase

et al. 2009

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We have developed a new and simple method based on "fluorous derivatization" for LC of native fluorescent compounds. This method involves the use of a column with a fluorous stationary phase. Native fluorescent analytes with target functional groups are precolumn derivatized with a nonfluorescent fluorous tag, and the fluorous-labeled analytes are retained in the column, whereas underivatized substances are not. Only the retained fluorescent analytes are detected fluorometrically at appropriate retention times, and retained substrates without fluorophores are not detected. In this study, biologically important carboxylic acids (homovanillic acid, vanillylmandelic acid, and 5-hydroxyindoleacetic acid) and drugs (naproxen, felbinac, flurbiprofen, and etodolac) were used as model native fluorescent compounds. Experimental results indicate that the fluorous-phase column can selectively retain fluorous compounds including fluorous-labeled analytes on the basis of fluorous separation. We believe that separation-oriented derivatization presented here is the first step toward the introduction of fluorous derivatization in quantitative LC analysis.

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Insights into the Retention Mechanisms on Perfluorohexylpropylsiloxane-Bonded (Fluophase-RP) and Octadecylsiloxane-Bonded (Betasil C18) Stationary Phases Based on the Same Silica Substrate in RP-LC

Cited by 29 publications

References 25 publications

Experimental Determination of LSER Parameters for a Set of 76 Diverse Pesticides and Pharmaceuticals

Experimental Determination of LSER Parameters for a Set of 76 Diverse Pesticides and Pharmaceuticals

Liquid chromatography/tandem mass spectrometry with fluorous derivatization method for selective analysis of sialyl oligosaccharides

Separation-Oriented Derivatization of Native Fluorescent Compounds through Fluorous Labeling Followed by Liquid Chromatography with Fluorous-Phase

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