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http://dx.doi.org/10.5012/bkcs.2005.26.3.393

Diaza-18-crown-6 Ethers Containing Partially-fluorinated Benzyl Sidearms: Effects of Covalently Bonded Fluorine on the Alkali Metal Complexation  

Chi, Ki-Whan (Department of Chemistry, University of Ulsan)
Shim, Kwang-Taeg (Department of Chemistry, University of Ulsan)
Huh, Hwang (Department of Chemistry, University of Ulsan)
Lee, Uk (Department of Chemistry, Pukyong National University)
Park, Young-Ja (Department of Chemistry, Sookmyung Women's University)
Publication Information
Bulletin of the Korean Chemical Society / v.26, no.3, 2005 , pp. 393-398 More about this Journal
Abstract
The stability constants for the diaza-18-crown-6 ethers 2-6 and alkali metal cations ($Na^+,\;K^+,\;Rb^+\;and\;Cs^+$) were determined using potentiometry in 95% methanol. For each metal ion the stability constants of the partiallyfluorinated ligands 3-6 were larger than that of the non-fluorinated ligand 2, which might reflect an interaction between fluorine atoms and alkali metal cations. The stability constant of the ligand 4 was larger than that of the ligand 5 for each metal cation tested. This finding was also supported by the results of cation-induced chemical shifts in $^1H-,\;^{19}F$-NMR and extraction experiment. The potentiometry and NMR results as well as the X-ray crystal structures revealed that the position and number of fluorine atoms in the benzyl side arms was crucial for the enhanced interaction between a ligand and an alkali metal.
Keywords
Diaza-18-crown-6 ethers; Partially-fluorinated benzyl sidearms; Alkali metal cation complexation; Stability constant;
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