What is so special about the sorption behavior of highly fluorinated compounds?

被引:72
作者
Goss, Kai-Uwe [1 ]
Bronner, Guido [1 ]
机构
[1] ETH, Inst Biogeochem & Pollutant Dynam, CH-8092 Zurich, Switzerland
关键词
PARTITION; FLUOROPHILICITY; DESIGN;
D O I
10.1021/jp062684o
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Highly fluorinated organic compounds are often said to exhibit unique sorption and partition properties. Terms such as "fluorophilicity" have been used to describe these properties, and fudge factors depending on the degree of fluorination have been used in predictive partition models to make them work for fluorinated solutes. Here we demonstrate that highly fluorinated compounds differ from other molecules only in that they exhibit van der Waals interactions much smaller than those of other molecules of same size. A simple cavity model for partitioning is shown to give good results for fluorinated compounds if the nonspecific interactions are correctly parametrized.
引用
收藏
页码:9518 / 9522
页数:5
相关论文
共 18 条
[1]  
Abraham M.H., 1994, J CHEM SOC PERK T 2, P1777
[2]   HYDROGEN-BONDING .27. SOLVATION PARAMETERS FOR FUNCTIONALLY-SUBSTITUTED AROMATIC-COMPOUNDS AND HETEROCYCLIC-COMPOUNDS, FROM GAS-LIQUID-CHROMATOGRAPHIC DATA [J].
ABRAHAM, MH .
JOURNAL OF CHROMATOGRAPHY, 1993, 644 (01) :95-139
[3]   THE USE OF CHARACTERISTIC VOLUMES TO MEASURE CAVITY TERMS IN REVERSED PHASE LIQUID-CHROMATOGRAPHY [J].
ABRAHAM, MH ;
MCGOWAN, JC .
CHROMATOGRAPHIA, 1987, 23 (04) :243-246
[4]   Solubility predictions for crystalline polycyclic aromatic hydrocarbons (PAHs) dissolved in organic solvents based upon the Abraham general solvation model [J].
Acree, WE ;
Abraham, MH .
FLUID PHASE EQUILIBRIA, 2002, 201 (02) :245-258
[5]  
[Anonymous], 1998, CRC Handbook of Chemistry and Physics
[6]  
ARP HP, UNPUB ENV SCI TECHNO
[7]  
Boublik T., 1984, The Vapour Pressures of Pure Substances, Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, DOI [10.1002/bbpc.19850890355, DOI 10.1002/BBPC.19850890355]
[8]  
Daubert T.E., 1997, PHYS THERMODYNAMIC P
[9]   Fast solvent screening via quantum chemistry: COSMO-RS approach [J].
Eckert, F ;
Klamt, A .
AICHE JOURNAL, 2002, 48 (02) :369-385
[10]  
Fowkes F.M., 1991, ACID BASE INTERACTIO, P93