Concepedia

An Attractive Interaction between the π-Cloud of C<sub>6</sub>F<sub>6</sub>and Electron-Donor Atoms

Ibón Alkorta, Isabel Rozas, José Elguero

The Journal of Organic Chemistry · 1997 · 181 citations · 25 references

TL;DR

The study investigates interactions between the π‑cloud of hexafluorobenzene and small electron‑donor molecules such as FH, HLi, :CH₂, NCH, and CNH. The authors employed HF, MP2, and B3LYP calculations with 6‑31G** and 6‑311++G** basis sets, and analyzed electron density topology via AIM and electrostatic potential maps of benzene and hexafluorobenzene. Database searches revealed examples of such π‑cloud interactions in crystal structures.

Abstract

A theoretical study of the possible interaction of the π-cloud of hexafluorobenzene (C6F6) with several small electron-donor molecules (FH, HLi, :CH2, NCH, and CNH) has been carried out. The calculations have been performed using HF, MP2, and hybrid HF/DFT methods (B3LYP) with the 6-31G** and 6-311++G** basis sets. The topology of the electron density of the complexes has been characterized using the AIM methodology. The characteristics of the electron density and molecular electrostatic potential maps of benzene and hexafluorobenzene have been compared. Finally, the results obtained from a search in the Cambridge Structural Database system of this kind of interaction are shown.