Sorption to dissolved organic matter (DOM) may influence significantly
the fate and the effects of organic pollutants in the aquatic environ
ment. To date, most studies on DOM-water partitioning have focused on
neutral hydrophobic compounds. Very little is known on the binding of
hydrophobic organic cations to DOM. In this study, the association of
triorganotin compounds (TOTs) with dissolved Aldrich and Suwannee Rive
r humic acids has been systematically investigated as a function of pH
and sodium perchlorate concentration. The organotin compounds studied
include the two widely used biocides tributyltin (TBT) and triphenylt
in (TPT) as well as other trialkyltin compounds of various hydrophobic
ities. Between pH 3 and pH 9, for both TBT and TPT, the overall DOM-wa
ter distribution ratio (D-DOM) was strongly pH-dependent and exhibited
a maximum close to the acidity constant (pK(a)) of the compounds. The
observed pH dependence of D-DOM could be described successfully with
a semiempirical discrete log K spectrum model. it was found that, over
the whole pH range investigated, sorption was governed by complexatio
n of the corresponding TOT cation (TOT+) by negatively charged ligands
(i.e., carboxylate and phenolate groups) of the humic acids. The dete
rmining factors of the TOT+ binding are postulated to be (i) complex f
ormation between the tin atom and the deprotonated ligands and (ii) hy
drophobic interactions. Significant differences in D-DOM of TBT were o
bserved between Suwannee River and Aldrich humic acid. D-DOM values of
TOTs determined for Aldrich humic acid were in the same range as part
iculate organic matter-water distribution ratios reported in the liter
ature for soils and sediments.