Organotin‐Substituted Crown Ethers for Ditopic Complexation of Anions and Cations

Abstract

Keywords: Ditopic complexation / Host-guest chemistry / NMR spectroscopy / X-ray crystallography / TinThe syntheses of the organotin-substituted crown ethers m-(Ph 2 XSnCH 2 CH 2 )-15-benzocrown-5 (2, X = Ph; 3, X = I; 4, X = Cl; 5, X = NCS) and the salt [m-(Ph 3 SnCH 2 CH 2 )-15-benzocrown-5·Na] + SCN -(2a) are reported. Compounds 2a and 4 (as its aqua complex 4·H 2 O) are characterized by single-crystal X-ray diffraction sudies. Multinuclear NMR spectroscopy and electrospray mass spectrometry reveal the triorganotin

Solubilizing Sodium Fluoride in Acetonitrile: Synthesis, Molecular Structure, and Complexation Behavior of Bis(organostannyl)methyl‐Substituted Crown Ethers

“…In compound B, the latter complexes sodium iodide through the crown ether moiety, but without charge separation. That is, (1) and Ph 2 ISnCH 2 Sn(I)(Ph)-CH 2 - [16]crown-5 (2) is reported. Both compounds have been characterized by elemental analyses, the Lewis acidity of the tin atom in compound B is not high enough to overcome the coulombic forces and to complex the iodide anion.…”

“…Both compounds have been characterized by elemental analyses, the Lewis acidity of the tin atom in compound B is not high enough to overcome the coulombic forces and to complex the iodide anion. Addition of tetrabutylammonium fluoride trihydrate, n-Bu 4 NF·3H 2 O, to a solution of B caused precipitation of sodium fluoride, NaF, and the quantitative formation of the triorganotin iodide Ph 2 ISnCH 2 - [16]crown-5. Apparently, the driving force for this reaction is the rather high lattice energy of sodium fluoride which cannot be compensated for by the complexing ligand.…”

“…This concept has been shown to be successful for an organoboron-substituted crown ether [13,14] which binds the ion pair potassium fluoride, KF, and for organotinsubstituted crown ethers which complex sodium thiocyanate, NaSCN, [15] and are able to transport it from aqueous solution through an organic phase. [16] Recently we reported the organotin-substituted crown ethers Ph (3Àn) X n SnCH 2 - [16]crown-5 (X = F, Cl, Br, I, SCN; n = 1, 2) and studied the complexation behavior of the chloro-substituted derivative A (n = 1, X = Cl) towards several salts. [17] Reaction of compound A with two molar equivalents of sodium iodide, NaI, quantitatively gave sodium chloride, NaCl, and the sodium iodide complex B of the corresponding iododiphenylstannyl-substituted crown ether.…”

“…[16] Recently we reported the organotin-substituted crown ethers Ph (3Àn) X n SnCH 2 - [16]crown-5 (X = F, Cl, Br, I, SCN; n = 1, 2) and studied the complexation behavior of the chloro-substituted derivative A (n = 1, X = Cl) towards several salts. [17] Reaction of compound A with two molar equivalents of sodium iodide, NaI, quantitatively gave sodium chloride, NaCl, and the sodium iodide complex B of the corresponding iododiphenylstannyl-substituted crown ether. In compound B, the latter complexes sodium iodide through the crown ether moiety, but without charge separation.…”

Close contacts involving germanium and tin in crystal structures: experimental evidence of tetrel bonds

“…Various other oxygen functionalities can act as donors of electron density to organotin and germanium derivatives, e.g., water [68][69][70], sulfoxides and sulfones [71][72][73][74], as well as TBs are depicted as black dotted lines. Color code: gray carbon, red oxygen, blue nitrogen, orange phosphorus, green chlorine, brown bromine, yellow sulfur, dark teal tin phosphine oxides, hexamethylphosphortriamide, and their analogs [75][76][77][78][79][80][81] (Fig.…”