Relationships between the chromatographic hydrophobicity indices and solute descriptors obtained by using several reversed-phase, diol, nitrile, cyclodextrin and immobilised artificial membrane-bonded high-performance liquid chromatography columns

Valkó, Klára; Plass, Monika; Bevan, Chris; Reynolds, Derek P.; Abraham, Michael H.

doi:10.1016/s0021-9673(97)00961-8

Cited by 129 publications

(48 citation statements)

References 27 publications

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“…1, and the point for any other system; we denote this distance as δ-PCA. We put these distances on a scale such that the distance between the point for the standard system and the point for the water-cyclohexane partition is 10, and we list the distances in Table 2.A technique that allows all of the information content in the coefficients to be used is that of nonlinear mapping (NLM), 50 as applied by Valko et al 51,52 Two components are obtained from the five coefficients, and a nonlinear map of the two components is shown in Figure 3. We calculate the distance in the xy plane between the point for a given system and the point for system no.…”

mentioning

confidence: 99%

Some Novel Liquid Partitioning Systems: Water−Ionic Liquids and Aqueous Biphasic Systems

Abraham¹,

Zissimos²,

Huddleston³

et al. 2003

Ind. Eng. Chem. Res.

188

152

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Partition coefficients, as values of log P, between water and two room-temperature ionic liquids and between water and an aqueous biphasic system have been correlated with Abraham's solute descriptors to yield linear free energy relationships that can be used to predict further values of log P, to ascertain the solute properties that lead to increased or decreased log P values, and to characterize the partition systems. It is shown that, in all three of the systems, an increase in solute hydrogen-bond basicity leads to a decrease in log P and an increase in solute volume leads to an increase in log P. For the two ionic liquid systems, an increase in solute hydrogenbond acidity similarly decreases log P, but for the aqueous biphasic system, solute hydrogenbond acidity has no effect on log P. These effects are rather smaller than those observed in traditional water-solvent systems. However, the ionic liquids appear to have an increased affinity for polyaromatic hydrocarbons as compared to traditional organic solvents. Principal component analysis and nonlinear mapping show that the three unconventional partition systems are considerably different from conventional water-organic solvent systems. IntroductionA major contemporary industrial challenge is to continued manufacturing beneficial chemical products while eliminating or substantially reducing the detrimental environmental consequences of the processes adopted. The Montreal Protocol 1 identified the need to reevaluate chemical processes to take account of their environmental impact, especially with regard to the use of volatile organic solvents. In addition, some 90% of hazardous waste is aqueous in nature, 2 and thus, industry is reliant upon efficient separations from liquid media. To this end, liquid-liquid separations are widely applied in the chemical process industry. Typically, because of their immiscibility with water, volatile organic solvents are often employed in such processes. 3 Taken together, these issues suggest that the elimination of the use of flammable toxic and volatile organic solvents in separations processing represents a significant step in the creation of a sustainable industrial technology. 4 A number of different approaches to this problem have been identified, including solvent-free synthesis, the use of water as a solvent, 5 the use of supercritical fluids, 6 and the use of ionic liquids. Recently, roomtemperature ionic liquids (RTILs) have received worldwide attention 7,8 as replacements for organic solvents in catalysis, 9 synthesis, 10,11 and separations processes. 12,13 Room-temperature ionic liquids, in contrast to conventional ionic liquids such as molten sodium chloride, which are only liquids at temperatures above 800°C, represent ionic salts that are liquid at room temperature. Many RTILs are liquids over a wide temperature range, and RTILs with melting points as low as -96°C are known. The constituents of many RTILs (being ionic) are constrained by high Coulombic forces and thus exert practically no vapor pressure abo...

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mentioning

confidence: 99%

Some Novel Liquid Partitioning Systems: Water−Ionic Liquids and Aqueous Biphasic Systems

Abraham¹,

Zissimos²,

Huddleston³

et al. 2003

Ind. Eng. Chem. Res.

188

152

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“…25 Ethylene glycol linkers are often preferred over aliphatic linkers due to the oxygen atoms that counterbalance the unpolar hydrocarbon parts of the linker. The gradient HPLC retention times, which can be used to substitute log P values, 26 were measured for the xylosides using a C-18 column and a mobile phase of water (0.1% TFA) with a gradient of MeCN from 1 minute increasing by 1.2% per minute ( Table 1). The retention times increased with increasing xylose-aglycon distances, which probably is a combined effect of a slightly decreased polarity and increased surface area of the xylosides.…”

Section: Synthesismentioning

confidence: 99%

Synthesis and biology of oligoethylene glycol linked naphthoxylosides

Holmqvist

Persson

Johnsson

et al. 2013

Bioorganic & Medicinal Chemistry

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“…Numerous equations have been published [63][64][65][66][67][68] for the characterisation of the various reversed phase of columns (C-18, perfluorinated hydrocarbons, cyclodextrin) using acetonitrile and methanol as an organic modifier in the mobile phase. The generally good statistical fit of the chromatographic retention data and the molecular descriptors derived from bulk organic solvent/water partition coefficients support the comparability of the two types of partition data.…”

Section: Analysis By the Solvation Equationmentioning

confidence: 99%

Application of High Performance Liquid Chromatography for the Measurements of Lipophilicity and Biomimetic Binding Properties in Drug Discovery

Valkó¹

2012

Physico-Chemical Methods in Drug Discovery and Development

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Relationships between the chromatographic hydrophobicity indices and solute descriptors obtained by using several reversed-phase, diol, nitrile, cyclodextrin and immobilised artificial membrane-bonded high-performance liquid chromatography columns

Cited by 129 publications

References 27 publications

Some Novel Liquid Partitioning Systems: Water−Ionic Liquids and Aqueous Biphasic Systems

Some Novel Liquid Partitioning Systems: Water−Ionic Liquids and Aqueous Biphasic Systems

Synthesis and biology of oligoethylene glycol linked naphthoxylosides

Application of High Performance Liquid Chromatography for the Measurements of Lipophilicity and Biomimetic Binding Properties in Drug Discovery

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