Publication: Octanol/water distribution coefficients of the C1 through C7 perfluoro-n-alkyl sulfonates: Comparison of the IEFPCM-UFF, CPCM, and SMD solvation models

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Title	Octanol/water distribution coefficients of the C1 through C7 perfluoro-n-alkyl sulfonates: Comparison of the IEFPCM-UFF, CPCM, and SMD solvation models
Authors/Editors*	S Rayne, K Forest
Where published*	Nature Precedings
How published*	Other
Year*	2010
Volume
Number
Pages
Publisher	Nature Publishing Group
Keywords	perfluoro-n-alkyl sulfonates; octanol/water distribution; solvation model; benchmarking; theoretical methods
Link	http://dx.doi.org/10.1038/npre.2010.5103.1
Abstract	The octanol/water distribution coefficients (log Dow) of the C1 through C7 perfluoro-n-alkyl sulfonates (PFSAs) were calculated using the M062X/6-311++G(d,p) and MP2/6-311++G(d,p)//M062X/6-311++G(d,p) levels of theory and the IEFPCM-UFF, CPCM, and SMD solvation models. At both levels of theory with all solvation models, absolute log Dow calculated for the straight chain C1 through C7 PFSAs display a substantial negative bias against available experimental data and expected trends by several log units. However, the SMD solvation model achieves accurate relative log Dow accuracy, yielding fragmental contributions of a -CF2- group towards the log Dow of 0.51+/-0.02 to 0.54+/-0.01 units (-3.0+/-0.1 to -3.1+/-0.1 kJ/mol), in good agreement with the experimental value of 0.61 units (-3.4+/-0.1 kJ/mol). In contrast, the IEFPCM-UFF and CPCM solvation models exhibit either invariant log Dow with increasing perfluoro-n-alkyl chain length (CPCM) or a modestly decreasing trend (IEFPCM-UFF).