A quantitative structure–activity relationships (QSAR) analysis of triarylmethane dye tracers

Dyes are important hydrological tracers. Many different dyes have been proposed as optimal tracers, but none of these dyes can be considered an ideal water tracer. Some dyes are toxic and most sorb to subsurface materials. The objective of this study was to find the molecular structure of an optimal water tracer. We used QSAR to screen a large number of hypothetical molecules, belonging to the class of triarylmethane dyes, in regard to their sorption characteristics to a sandy soil. The QSAR model was based on experimental sorption data obtained from four triarylmethane dyes: C.I. Food Blue 2 (C.I. 42090; Brilliant Blue FCF), C.I. Food Green 3 (C.I. 42053; FD&C Green No. 3), C.I. Acid Blue 7 (C.I. 42080; ORCOacid Blue A 150%), and C.I. Acid Green 9 (C.I. 42100; ORCOacid Fast Green B). Sorption characteristics of the dyes to the sandy soil were expressed with the Langmuir isotherm. Our premise was that dye sorption can be reduced by attachment of sulfonic acid (SO3) groups to the triarylmethane template. About 70 hypothetical dyes were created and QSAR were used to estimate sorption characteristics. The results indicated that both the position and the number of SO3 groups affected dye sorption. Sorption decreased with increasing number of SO3 groups attached to the molecule. Increasing the number of sulfonic acid groups also decreases the toxicity of the compounds. An optimal triarylmethane water tracer contains 4 to 6 SO3 groups.