The solid state and solution conformational behaviour of a chiral 30-crown-10 derivative synthesised from 1,4:3,6-dianhydro-D-mannitol; X-ray crystal structure

Abstract

A chiral 30-crown-10 derivative. DD-(2), has been prepared from 1,4:3,6-dianhydro-D-mannitol, D-(1), and shown by X-ray crystallography and dynamic ¹³C n.m.r. spectroscopy to adopt, in both the solid state and in solution, a ‘face-to-back’ conformation which must undergo substantial change in order to create the hydrophilic cavity necessary for the formation of complexes with Li⁺, Na⁺, K⁺, Rb⁺, NH₄⁺, MeNH₃⁺, and Bu^tNH₃⁺ ions.