The CH−π Interactions of Methyl Ethers as a Model for Carbohydrate–N‑Heteroarene Interactions

CH−π interactions have been cited as an important contributor to carbohydrate recognition. To determine whether N-heterocycles form stronger CH−π interactions, the interactions of methyl ether groups with heterocyclic and nonheterocyclic aromatic surfaces were studied. Both experimental and computational experiments found that N-heterocyclic aromatic surfaces formed stronger interactions. This enhancement was attributed to attractive dipole–dipole interactions between the methyl ether C–O bond and the N-heterocyclic aromatic dipole.