Effect of ortho-chlorine substitution on the partition behavior of chlorophenols.
Chlorophenol isomers are known to possess substantially different octanol/water and octane/water partition constants depending on whether the chlorine substituents are in the ortho or meta/para position. Here we show that the same is also true for environmental partition processes such as water/air and humic acid/air partitioning. Quantitative structure property relationships (QSPR) such as those in the widely used EPI-suite or SPARC fail to correctly predict this influence of the substituent position on the compound's partitioning. Only a more sophisticated quantum chemical software, called COSMOtherm, correctly reproduced these effects. Based on this and earlier experiences we conclude that COSMOtherm may be a better tool for screening large sets of chemicals for which no experimental data on their partitioning yet exist.
Niederer
Christian
C
Institute of Biogeochemistry and Pollutant Dynamics, ETH-Zurich, Universitätsstrasse 16, CH-8092 Zurich, Switzerland.
Goss
Kai-Uwe
KU
D000327:Adsorption; D000388:Air; D005591:Chemical Fractionation; D002713:Chlorine / Q000737:chemistry*; D002733:Chlorophenols / Q000737:chemistry*; D008956:Models, Chemical; D000442:Octanols / Q000737:chemistry; D012984:Software; D012987:Soil; D014867:Water / Q000737:chemistry
D002733:Chlorophenols; D000442:Octanols; D012987:Soil; D014867:Water; D002713:Chlorine