Binding of alkyl halides in water-soluble cavitands with urea rims

Abstract

The complexation of primary alkyl halides C_n–X (n = 5, 6 and 9; X = Cl, Br and I) in a new, water-soluble cavitand is evaluated. The complexes are dynamic; the host and guest adapt their shapes to accommodate each other and the guest undergoes tumbling or yo–yo like motions in the space. Evidence for halogen bonding of the halides to the aryl surfaces of the cavitand is presented.