Abstract
Lipophilic derivatives of benzo-12-crown-4 and naphtho-12-crown-4 have been synthesized. The behavior of the parent compounds and their derivatives in membrane ion-selective electrodes have been studied. Selectivity changes have been observed with the rise in lipophilicity. Crystal structures of the NaI and KI complexes of benzo-12-crown-4 (1 and2) have been determined by X-ray analysis. The alkali metal and iodide ions are in direct contact in2 but not in1. Compound1 [Na(benzo-12-crown-4)2]·I is triclinic, witha=13.368(8),b=10.727(7),c=10.325(4) Å; α=73.56(4),β=77.73(4), γ=108.70(5)°;Z=2, space group is\(P\bar 1\). Compound2 [K(benzo-12-crown-4)2·I] is monoclinic, witha=15.807(8),b=12.043(4),c=15.601(6) Å,β=117.74(3)°;Z=4, space groupC2/c. In both compounds the cations interact with all oxygen atoms of two crown ether molecules. Correlation of the crystal structures and behavior of the crown ethers in ion-selective membrane electrodes is discussed.
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Supplementary Data related to this article have been deposited with the British Library as Supplementary Publication No. 82185 (15 pages).
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Luboch, E., Dvorkin, A.A. & Simonov, Y.A. 12-Membered crown ethers. Lipophilic derivatives of benzo- and naphtho-12-crown-4 and their membrane electrode properties. Crystal structures of benzo-12-crown-4 NaI and KI complexes. J Incl Phenom Macrocycl Chem 20, 335–351 (1994). https://doi.org/10.1007/BF00708878
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DOI: https://doi.org/10.1007/BF00708878