84227-47-4Relevant articles and documents
Synthesis of monoazacrown ethers under phase-transfer catalysis
Luk'yanenko,Basok,Kulygina, E. Yu.,Bogashchenko, T. Yu.,Yakovenko
, p. 1345 - 1352 (2013/02/22)
A procedure has been proposed for the synthesis of monoazacrown ethers by reaction of N-benzyldiethanolamine with oligo(ethylene glycol) bis-p-toluenesulfonates in a two-phase system aromatic hydrocarbon-50% aqueous alkali, followed by removal of the benzyl group by catalytic hydrogenolysis. The maximal yields of N-benzylaza-12-crown-4, -18-crown-6, and -21-crown-7 were achieved by adding 4-10 equiv of LiCl, BaBr2, and CsCl, respectively, to the reaction mixture, which probably indicated template effect. Pleiades Publishing, Ltd., 2012.
Cation Binding Properties and Molecular Structure of the Crystalline Complex (Aza-12-crown-2)2*NaI
White, Banita D.,Arnold, Kristin A.,Garrell, Robin L.,Fronczek, Frank R.,Gandour, Richard D.,Gokel, George W.
, p. 1128 - 1133 (2007/10/02)
Aza-12-crown-4 forms a 2:1 sandwich complex similar to that known for 12-crown-4 sodium iodide, except that the presence of >NH in each ring makes Na-donor bonds unequal in strength and leads to hydrogen bonding with the counterion.The heteroatoms of each macroring are coplanar, and both nitrogens are on the same side of the complex (twist angle 43 deg from eclipsed).This may be due to a long (and weak) hydrogen bond to iodide, an interaction confirmed by analysis using Raman spectroscopy.The previously unreported 1:1 and 2:1 cation affinity constants (anhydrous MeOH , 25 deg C) for this macrocycle are logKS(1:1) = 1.3 +/- 0.1 and logKS(2:1) = 2.0 +/- 0.1, respectively.
SYNTHESES AND CATION BINDING PROPERTIES OF 12-MEMBERED RING NITROGEN-PIVOT LARIAT ETHERS
White, Banita D.,Dishong, Dennis M.,Minganti, Carlo,Arnold, Kristin A.,Goli, D.M.,Gokel, George W.
, p. 151 - 154 (2007/10/02)
The efficient synthesis of several 12-membered ring, N-pivot lariat ethers are reported and it is shown that binding to sodium cations is weak except when an oligoethyleneoxy sidearm is long enough to provide additional solvation.