Abstract
The crystal structure of α-d-mannosido-benzo-18-crown-6·KSCN (1) was solved by X-ray single crystal diffractometry. C28H36O10·KSCN is orthorhombic, space groupP212121 withZ=4,a=8.035(4),b=9.960(2),c=38.83(2) Å,M r =629.8,V=3103.6 Å3,D x =1.347 g cm−3, μ(CuKα)=2.53 mm−1, λ=1.54178 Å,F(000)=1324. FinalR=0.043 for 1139 unique observed reflections measured at room temperature. The potassium ion is surrounded by a nearly planar hexagon of oxygen atoms of the macrocyclic ring and lies on the plane formed by those atoms. Hexagonal pyramidal coordination is completed by the nitrogen atom of the thiocyanate anion. The SCN ion was found on the face of the macrocyclic ring opposite that for the chiral mannopyranoside moiety. The molecular structure of α-d-mannosido-18-crown-6 (2) and the structure of molecular complexes of2 and α-d-glucosido-benzo-18-crown-6 (3) were studied by molecular mechanics methods. The results suggest enthalpy driven selectivity of complexation of the phenylalanine methyl ester (4) by2 and both enthalpy and entropy effects in selective complexation of4 by3.
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Supplementary Data relating to this article are deposited with the British Library as supplementary publication No. SUP 82061 (20 pages).
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Suwińska, K., Lipkowski, J. Numerical modelling of inclusion-type complexes formed by chiral 18-crown-6 ethers bearing sugar moieties with enantiomers of phenylalanine methyl ester cations. Journal of Inclusion Phenomena 6, 237–248 (1988). https://doi.org/10.1007/BF00682136
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DOI: https://doi.org/10.1007/BF00682136