American Chemical Society
ol502418k_si_002.cif (23.99 kB)

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

Download (23.99 kB)
posted on 2014-10-03, 00:00 authored by Ping Li, Trent M. Parker, Jungwun Hwang, Fengyuan Deng, Mark D. Smith, Perry J. Pellechia, C. David Sherrill, Ken D. Shimizu
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.