84131-05-5Relevant articles and documents
Crown Cation Complex Effects. 20. Syntheses and Cation Binding Properties of Carbon-Pivot Lariat Ethers
Dishong, Dennis M.,Diamond, Craig J.,Cinoman, Michael I.,Gokel, Geoge W.
, p. 586 - 593 (2007/10/02)
In an effort devise synthetic cation binders that will mimic the behavior of naturally occuring ionophores such as valinomycin, we have prepared approximately 30 macrocyclic (crown) polyethers bearing flexible side chains attached to the macro ring at carbon.In many of these "carbon-pivot" compounds, the side chain contains one or more neutral donor groups that, if in a suitable geometrical arrangement, may provide additional solvation to the macro-ring-bound cation.Although such donors often enhanced the cation binding ability, overall, the increases in stability constants were modest.The physical resemblance and concept of "roping and tying" the cation suggest the name "lariat ethers".Syntheses of these molecules and binding by them of Na+ and K+ cations are reported and conclusions drawn about the structural requirements and cation binding efficacy of these materials.
Enhancement of Cation Binding in Lariat Ethers Bearing a Methyl Group at the Quaternary, Pivot Carbon Atom
Nakatsuji, Yohji,Nakamura, Tetsuya,Okahara, Mitsuo,Dishong, Dennis M.,Gokel, George W.
, p. 1237 - 1242 (2007/10/02)
A number of carbon-pivot lariat ethers have been prepared and compared, with their counterparts having a methyl group bonded to the side-arm-bearing or pivot carbon.All of the compounds examined are 15-crown-5 derivatives, and in this series, the methyl lariats invariably show a higher affinity for sodium than do the nonmethylated species.The results are less consistent in the case of potassium cation which is larger than the 15-crown-5 compound's cation binding hole.The enhanced stability constant observed for sodium with the methyl lariats is attributed to reduced s ide-arm mobility or conformational changes in either the side arm or macroring.
LARIAT ETHERS. VI. EVIDENCE FOR INTRAMOLECULAR CHELATION IN SODIUM AND POTASSIUM CATION BINDING BY 15-CROWN-5, CARBON-PIVOT LARIAT ETHERS
Goli, Deepa, M.,Dishong, Dennis, M.,Diamond, Craig, J.,Gokel, George, W.
, p. 5243 - 5246 (2007/10/02)
The first compelling evidence for intramolecular sidearm involvement in sodium and potassium cation complexation by carbon-pivot lariat ethers is presented.