The White–Bovill alkane–alkene force field (WBFF) has been slightly modified and extended for the calculation of geometrical and thermodynamic properties of saturated compounds containing the isolated ether or the 1,4-dioxa grouping. The new force field reproduces the heats of formation of 14 ethers with a mean deviation of 0.86 kcal mol–1 between observed and calculated enthalpies. Bond lengths, bond angles, and torsion angles are satisfactorily reproduced with mean deviations of 0.010 Å, 1.0°, and 4.3° respectively over a set of 103 observations. The force field has been used to investigate the detailed relationship between the strain energies and the corresponding equilibrium geometries of various conformations of 9-crown-3, 12-crown-4, and 18-crown-6. The determination of the structure of the complex of 18-crown-6 with benzylammonium thiocyanate, by X-ray crystallography, is described and molecular mechanics calculations are used to comment upon the conformations adopted by 18-crown-6 in a range of complexes.
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Bovill et al. (1980) studied this question.
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