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Substituent Effects On The Binding Of Halides By Neutral And Dicationic Bis-Triazolium Receptors, Binod Nepal, Steve Scheiner
Substituent Effects On The Binding Of Halides By Neutral And Dicationic Bis-Triazolium Receptors, Binod Nepal, Steve Scheiner
Chemistry and Biochemistry Faculty Publications
The effects of substituent and overall charge upon the binding of a halide anion by a bis-triazolium receptor are studied by M06-2X DFT calculations, with the aug-cc-pVDZ basis set. Comparison is also made between a receptor that engages in H-bonds, with a halogen-bonding species. Fluoride is clearly most strongly bound, followed by Cl-, Br-, and I- in that order. The dicationic receptor engages in stronger complexes, but not by a very wide margin compared to its neutral counterpart. The binding is enhanced as the substituent on the two triazolium rings becomes progressively more electron-withdrawing. Halogen-substituted receptors, whether neutral or cationic, …
Competitive Halide Binding By Halogen Versus Hydrogen Bonding: Bis-Triazole Pyridinium, Binod Nepal, Steve Scheiner
Competitive Halide Binding By Halogen Versus Hydrogen Bonding: Bis-Triazole Pyridinium, Binod Nepal, Steve Scheiner
Chemistry and Biochemistry Faculty Publications
The binding of F-, Cl-, Br-, and I- anions by bis‐triazole‐pyridine (BTP) was examined by quantum chemical calculations. There is one H atom on each of the two triazole rings that chelate the halide via H bonds. These H atoms were replaced by halogens Cl, Br, and I, thus substituting H bonds by halogen bonds. I substitution strongly enhances the binding; Br has a smaller effect, and Cl weakens the interaction. The strength of the interaction is sensitive to the overall charge on the BTP, rising as the binding agent becomes singly and then doubly positively charged. The strongest preference …