Ja. Leenheer et al., STRONG-ACID, CARBOXYL-GROUP STRUCTURES IN FULVIC-ACID FROM THE SUWANNEE RIVER, GEORGIA .2. MAJOR STRUCTURES, Environmental science & technology, 29(2), 1995, pp. 399-405
Polycarboxylic acid structures that account for the strong-acid charac
teristics (pK(a1) near 2.0) were examined for fulvic acid from the Suw
annee River. Studies of model compounds demonstrated that pK, values n
ear 2.0 occur only if the alpha-ether or alpha-ester groups were in cy
clic structures with two to three additional electronegative functiona
l groups (carboxyl, ester, ketone, aromatic groups) at adjacent positi
ons on the ring. Ester linkage removal by alkaline hydrolysis and dest
ruction of ether linkages through cleavage and reduction with hydriodi
c acid confirmed that the strong carboxyl acidity in fulvic acid was a
ssociated with polycarboxylic alpha-ether and alpha-ester structures.
Studies of hypothetical structural models of fulvic acid indicated pos
sible relation of these polycarboxylic structures with the amphiphilic
and metal binding properties of fulvic acid.