Preparation and characterization of a halogen-bonded shape-persistent chiral alleno-acetylenic inclusion complex

Org Lett. 2014 Feb 21;16(4):1136-9. doi: 10.1021/ol403778f. Epub 2014 Feb 10.

Abstract

A chiral bidentate inclusion complex has been formed by halogen-bond interaction between the pyridyl moieties of a pyridoallenoacetylenic host and octafluorodiiodobutane. X-ray crystallography showed that the guest adopts a chiral conformation inside the molecular channels formed by stacking of the host units. A 10 ppm shielding of the (15)N NMR resonance for the pyridil units provided evidence of the formation of the halogen-bond complex in solution.