Solid-state and computational studies of anion-π interactions

ORGN 702

Christa Anderson, cander19@SLU.EDU, Chaidez Matthew, chaidezm@SLU.EDU, and Michael Lewis, LewisM5@slu.edu. Department of Chemistry, Saint Louis University, 3501 Laclede Avenue, Saint Louis, MO 63103
Computational studies have shown interactions between anions and aromatic π-electron density may exist when the aromatic is electron deficient. Recent solid-state investigations have shown anions will bind to the face of transition metal complexed aromatics with the general structural motif [TMn+–Ar–A–] where TMn+ is a transition metal with positive charge n, Ar is the aromatic, and A– is the anion. Obviously, the complexation of the transition metal to the face of the aromatic makes the arene electron deficient and thus this approach is in agreement with the computational work. However, most of the computational work on arene-anion complexes used electron-withdrawing substituents to produce electron deficient aromatics. We will present the synthesis of a model host that allows for the investigation of anion-π interactions of aromatics that are not complexed with transition metals, but instead have aromatics with electron-withdrawing substituents. We will also present computational studies aimed at determining whether anion-arene interactions involving transition metal complexed aromatics prefer arene-binding at the face of the aromatic or at the transition metal.