Organotin-Substituted [13]-Crown-4 Ethers: Ditopic Receptors for Lithium and Cesium Halides

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The synthesis of the organotin- and the bis(organostannyl)methane-substituted crown ethers Ph(3−n)XnSnCH2-[13]-crown-4 (1, n = 0; 2, n = 1, X = I; 3, n = 1, X = Cl; 4, n = 1, X = F; 5, n = 2, X = I; 6, n = 3, X = I; 8, n = 3, X = Cl; 9, n = 2, X = Cl) and Ph(3−n)XnSnCH2Sn(X)nPh(2−n)CH2-[13]-crown-4 (10, n = 0; 11, n = 1, X = I; 12, n = 2, X = I; 13, n = 1, X = F; 14, n = 2, X = Cl) as well as of the ditopic complexes 8·LiCl·H2O and Ph2(SCN)SnCH2-[13]-crown-4·LiSCN (15·LiSCN) are reported. These compounds were characterized by elemental analyses, by 1H, 13C, 19F, and 119Sn NMR spectroscopy, electrospray mass spectrometry, and in the case of 2 and 4 also by 119Sn MAS NMR spectroscopy. Single-crystal X-ray diffraction analyses reveal distorted tetrahedral configurations for the tin atoms in compounds 1, 11 (Sn2), and 12 (Sn2), whereas intramolecular O→Sn interactions (Sn−O = 2.416(2) (6) to 2.471(3) (11, Sn1) A) characterize the molecular structures of compounds 2, 6, 9, and 11 (Sn1), in which the tin atoms ...