The effect of the hydrogen fluoride chain on the aromaticity of C6H6 in the C6H6···(HF)1–4 complexes

Abstract

ABSTRACTThe effect of the hydrogen fluoride chain ((HF)n) on the aromaticity and π character of C–C bonds of C6H6 in the C6H6···(HF)n (n = 1–4) complexes were investigated using density functional theory employing RM05 functional. It was found that the binding energy between C6H6 and different (HF)n chains showed a maximum at n = 3 (C6H6···(HF)3). Also, the π–hydrogen interaction (πHI) and the bifurcated fluorine interaction (BFI) increased and decreased the π character of the C–C bond of C6H6, respectively. In addition, the change of aromaticity of the C6H6 due to the interaction with the HF chains was also studied using three different aspects such as aromatic fluctuation index (FLU), average two centre index (ATI) and proton nuclear magnetic resonance (HNMR) spectrum. The most change in the aromaticity happens when the C6H6 interacts with (HF)3 chain. The variation of aromaticity with the binding energy and the summation of two-body terms were investigated and very good linear correlations were observed.