Determination of descriptors for polycyclic aromatic hydrocarbons and related compounds by chromatographic methods and liquid–liquid partition in totally organic biphasic systems

Ariyasena, Thiloka C.; Poole, Colin F.

doi:10.1016/j.chroma.2014.08.008

Cited by 24 publications

(2 citation statements)

References 72 publications

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“…Data are available for many substances, most of which come from indirect gas chromatographic measurements. − ,,, When using a nonpolar GC column and under isothermal conditions, according to the pp-LFER approach, the logarithmic retention time log t ret of an organic compound according to eq depends linearly on both the log K HdA ( L ) value and the McGowan volume V McG …”

Section: Resultsmentioning

confidence: 99%

“…Experimental techniques are also applied and numerous devices are available to determine K OA , − K OW , − and K HdA , − but only few authors − critically discuss the challenges and pitfalls of methods to measure K OW . Experimental work must also take into account that a certain amount of water is soluble in 1-octanol and vice versa. , The mutual solubility of n -hexadecane and water is negligible (see Supporting Information).…”

Section: Introductionmentioning

confidence: 99%

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Quantum Chemical Calculation and Evaluation of Partition Coefficients for Classical and Emerging Environmentally Relevant Organic Compounds

Salthammer

Grimme

Stahn

et al. 2021

Environ. Sci. Technol.

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Octanol/water (K OW), octanol/air (K OA), and hexadecane/air (K HdA) partition coefficients are calculated for 67 organic compounds of environmental concern using computational chemistry. The extended CRENSO workflow applied here includes the calculation of extensive conformer ensembles with semiempirical methods and refinement through density functional theory, taking into account solvation models, especially COSMO-RS, and thermostatistical contributions. This approach is particularly advantageous for describing large and nonrigid molecules. With regard to K OW and K HdA, one can refer to many experimental data from direct and indirect measurement methods, and very good matches with results from our quantum chemical workflow are evident. In the case of the K OA values, however, good matches are only obtained for the experimentally determined values. Larger systematic deviations between data computed here and available, nonexperimental quantitative structure–activity relationship literature data occur in particular for phthalic acid esters and organophosphate esters. From a critical analysis of the coefficients calculated in this work and comparison with available literature data, we conclude that the presented quantum chemical composite approach is the most powerful so far for calculating reliable partition coefficients because all physical contributions to the conformational free energy are considered and the structure ensembles for the two phases are generated independently and consistently.

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