Partition Coefficients for Environmentally Important, Multifunctional Organic Compounds in Hexane + Water

Schulte, Jan S.; Dürr, J.; Ritter, Simone; Hauthal, Werner H.; Quitzsch, and K.; Maurer, Gerd

doi:10.1021/je970112e

Cited by 24 publications

(21 citation statements)

References 10 publications

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“…The CG MD model was parametrized to give a value of -7 kcal/mol, which is in agreement with the experimental value of -6.9 kcal/mol. [35][36][37][38][39] Again, no interfacial activity is predicted for toluene at the interface existing between hexane and water. The volume-corrected experimental transfer free-energy data (water-to-hexane) for p-cresol give a value of -2.9 kcal/mol in going from water to hexane.…”

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confidence: 99%

Coarse-Grained Potential Models for Phenyl-Based Molecules: I. Parametrization Using Experimental Data

et al. 2010

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A coarse-grained intermolecular potential has been parametrized for phenyl-based molecules. The parametrization was accomplished by fitting to experimental thermodynamic data. Specifically, the intermolecular potentials, which were based on Lennard-Jones functional forms, were parametrized and validated using experimental surface tension, density, and partitioning data. This approach has been used herein to develop parameters for coarse-grained interaction sites that are applicable to a variety of phenyl-based molecules, including analogues of the amino acid side chains of phenylalanine and tyrosine. Comparison of the resulting coarse-grain model to atomistic simulations shows a high level of structural and thermodynamic agreement between the two models, despite the fact that no atomistic simulation data was used in the parametrization of the coarse-grain intermolecular potentials.

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confidence: 99%

Coarse-Grained Potential Models for Phenyl-Based Molecules: I. Parametrization Using Experimental Data

et al. 2010

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“…All of the NPs have much more negative values for b than SDS micelles, indicating much lower affinity for basic compounds. As a point of reference, the reported value of b for transfer of solutes from water to hexane, a nonacidic hydrocarbon, is −4.64 , suggesting that the NP PSPs afford only very weak interactions with basic compounds. A similar large negative value is reported for a random copolymer of AMPS and dodecyl methacrylate (poly(C 12 Mat/AMPS) , suggesting that the acrylate and acrylamide groups on these polymer backbones do not facilitate interactions with basic solutes.…”

Section: Resultsmentioning

confidence: 99%

RAFT polymerized nanoparticles: Influences of shell and core chemistries on performance for electrokinetic chromatography

et al. 2014

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The performance and solvation characteristics of two novel latex nanoparticle (NP) pseudo-stationary phases (PSPs) for EKC are determined and compared to those of previously reported micellar, polymeric, and NP materials. The new NPs have shells composed of strongly acidic poly(AMPS) as opposed to the poly(acrylic acid) shell of the prior NP, and have varied hydrophobic core chemistry of either poly(butyl acrylate) or poly(ethyl acrylate). The NPs poly(AMPS) shell shows only minor changes in mobility and selectivity between pH 4.9 and 9.4, allowing adjustment of pH to influence and optimize separation performance. All of the NP phases have significantly different solvation characteristics and selectivity relative to SDS micelles. The selectivity and solvent character are similar for NPs with poly(butyl acrylate) cores and different shells, but vary significantly between NPs with poly(butyl acrylate) versus poly(ethyl acrylate) cores. NPs with poly(butyl acrylate) cores are among the least cohesive PSPs reported to date, while the NP with poly(ethyl acrylate) core is among the most cohesive. The results demonstrate that PSPs with unique selectivity can be generated by altering the chemistry of the hydrophobic core.

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“…18;38;53-67 To expand the pool, 145 alkane/water (A/W) partition coefficients were also collected 18;38;53-61;64;65 and used to predict the C16/W partition coefficients for additional 208 compounds. All used data are listed in Table S1 in Supporting Information.…”

Section: Methodsmentioning

confidence: 99%

“…The solvation properties of the bilayer core can be, thanks to similar densities and composition, 15 emulated by n-hexadecane (C16) 16 or other alkane/alkene, such as 2,4,4-trimethylpentane, 17 n-hexane, 18 n-heptane, 19 isooctane, 20 n-decane, 21 n-dodecane, 22 1-hexadecene, 1,9-decadiene, 21 or loosely defined alkane mixtures. 23 The partition coefficients of compounds in different alkane/water systems have quite similar magnitudes.…”

Section: Introductionmentioning

confidence: 99%

Structural Determinants of Drug Partitioning in n-Hexadecane/Water System

Natesan

Wang

Lukáčová

et al. 2013

J. Chem. Inf. Model.

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Surrogate phases have been widely used as correlates for modeling transport and partitioning of drugs in biological systems, taking advantage of chemical similarity between the surrogate and the phospholipid bilayer as the elementary unit of biological phases, which is responsible for most of transport and partitioning. Solvation in strata of the phospholipid bilayer is an important drug characteristics because it affects the rates of absorption and distribution, as well as the interactions with the membrane proteins having the binding sites located inside the bilayer. The bilayer core can be emulated by n-hexadecane (C16), and the headgroup stratum is often considered a hydrophilic phase because of the high water content. Therefore, we tested the hypothesis that the C16/water partition coefficients (P) can predict the bilayer locations of drugs and other small molecules better than other surrogate systems. Altogether 514 PC16/W values for nonionizable (458) and completely ionized (56) compounds were collected from the literature or measured, when necessary. With the intent to create a fragment-based prediction system, the PC16/W values were factorized into the fragment solvation parameters (f) and correction factors based on the ClogP fragmentation scheme. A script for the PC16/W prediction using the ClogP output is provided. To further expand the prediction system and reveal solvation differences, the fC16/W values were correlated with their more widely available counterparts for the 1-octanol/water system (O/W) using solvatochromic parameters. The analysis for 50 compounds with known bilayer location shows that the available and predicted PC16/W and PO/W values alone or the PC16/O values representing their ratio do not satisfactorily predict the preference for drug accumulation in bilayer strata. These observations indicate that the headgroups stratum, albeit well hydrated, does not have solvation characteristics similar to water and is also poorly described by the O/W partition characteristics.

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Partition Coefficients for Environmentally Important, Multifunctional Organic Compounds in Hexane + Water

Cited by 24 publications

References 10 publications

Coarse-Grained Potential Models for Phenyl-Based Molecules: I. Parametrization Using Experimental Data

Coarse-Grained Potential Models for Phenyl-Based Molecules: I. Parametrization Using Experimental Data

RAFT polymerized nanoparticles: Influences of shell and core chemistries on performance for electrokinetic chromatography

Structural Determinants of Drug Partitioning in n-Hexadecane/Water System

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