Aromatic Interactions

Abstract

Aromatic sidechains are special for many reasons. First of all, they are just big relative to other sidechains. But they also have a subtle dual role as hydrophobic groups and as acceptors in polar interactions (e.g., as hydrogen bond acceptors (Adams et al in Chem Commun pp 2531–2532, 1996, [2])). Their delocalized $\pi$-electronic cloud is highly polarizable and enables interactions with cations, so-called cation-$\pi$ interactions.