Search for diastereoisomers of the 3,5-bis(trifluoromethyl)phenyl dinaphtho propeller crowns: crystal structure and molecular dynamics simulations

Abstract

The crystal structure of the propeller crown 2-[3,5-bis(trifluoromethyl)phenyl]-4,7, 10, 13, 16, 19-hexaoxa-3(1,2), 1(2, 1)-dinaphthenacyclononadecaphane has been shown to contain the isomer B of the propeller. Molecular dynamics studies of a discrete molecule in vacuo, with Coulomb interactions dampened by an effective dielectric constant (relative permittivity), of this and the alternative A isomer help to explain the behaviour of the crown in solution: the propeller section is preorganised while the macrocycle section is mobile on a ps–ns timescale.