Insights into complexation and enantioselectivity of uranyl-2-(2-hydroxy-3-methoxyphenyl)-9-(2-hydroxyphenyl)thiopyrano[3,2-h]thiochromene-4,7-dione with R/S-organophosphorus pesticides

In order to explore the enantioselectivity of new uranyl receptors to chiral organophosphorus pesticides (COPs), we designed a novel ligand: 2-(2-hydroxy-3-methoxyphenyl)-9-(2-hydroxyphenyl)thiopyrano[3,2-h]thiochromene-4,7-dione (HTTDN) and constructed a new receptor of Uranyl-HTTDN by complexation of HTTDN with uranyl. The complexation and enantioselectivity of Uranyl-HTTDN to COPs of R/S-methamidophos (R/S-MAPs) and R/S-acephates (R/S-APs) were studied using density functional theory (DFT) method in this paper. The results showed that in vacuum and toluene, Uranyl-HTTDN could effectively recognize R/S-MAPs by complexation with oxygen of phosphoryl of methamidophos, with enatioselectivity coefficients of 91.80% and 86.74%, respectively. In vacuum, water, and acetone, Uranyl-HTTDN could also effectively identify R/S-APs by the oxygen of phosphoryl coordinating with U, and enatioselectivity coefficients toward R/S-APs were 99.41%, 91.09%, and 93.84%, respectively. These results could provide valuable information and theoretical reference for the further experiments of COPs separation.

Automated summary

The novel receptor Uranyl-HTTDN showed high enantioselectivity towards chiral organophosphorus pesticides R/S-MAPs and R/S-APs by complexation with uranyl. This provides valuable theoretical reference and information for further experiments on the separation of COPs.