Heteroatoms in Parallel-Displaced Stacking

Stacking interactions between aromatic rings play a critical role in a wide array of
chemical and biological processes. A deeper understanding of these interactions has applications in fields ranging from drug design to the development of more efficient organic photovoltaic systems. It is well-known that most aromatic systems prefer to stack at parallel displaced positions as opposed to face to face. We explore the impact of heteroatoms on the geometry and interaction energy of parallel displaced stacked dimers using quantum chemistry calculations, and propose a simple model that explains these results.