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Probing Orientation-Specific Charge-Dipole Interactions between Hexafluoroisopropanol and Halides: A Joint Photoelectron Spectroscopy and Theoretical Study.

The interactions between hexafluoroisopropanol (HFIP) and halogen anions X‒ (F‒, Cl‒, Br‒, and I‒) have been investigated by negative ion photoelectron spectroscopy (NIPES) and ab initio calculations. The measured NIPE spectrum of each [HFIP·X]‒ (X = Cl, Br, and I) complex shows the identical pattern to the corresponding X‒ by shifting to the high electron binding energy side, indicative of formation of [HFIP···X‒] structure, in which X‒ interacts with HFIP via charge-dipole interactions. However, the spectrum of [HFIP·F]‒ appears completely different from that of F‒, and is more similar to the spectrum of the deprotonated HFIP anion (HFIP‒H‒). The geometry and electron density calculations indicate that a neutral HF molecule is formed upon HFIP interacting with F‒ via proton transfer, rendering a stable structure of [HFIP‒H···HF]‒. Two conformers of [HFIP‒H·HF]‒ with HFIP being in synperiplanar and antiperiplanar configurations, respectively, are observed, providing direct experimental evidences to show the distinctly different and orientation-specific interactions between HFIP and halide anions.