cis-Cyclohexano-9-crown-3 ether. Solid state and low-temperature solution stereochemistry as determined by X-ray crystallography and nuclear magnetic resonance spectroscopy

Abstract

The X-ray crystal structure of the title material has been determined at −130 °C. Low-temperature 1H1H COSY, 13C1H HETCOR, and DEPT 13C NMR spectra have been recorded, which permit unambiguous assignments of all carbon resonances when ring inversion is slow on the NMR timescale. The limiting low-temperature solution phase 13C spectrum has many common features with the solid phase 13C CPMAS spectrum recorded at 300 K. Spectra for the 7,10-tetra-deuterio derivative have also been obtained and substituent influences on 13C shieldings are discussed in detail.