Journal of Organic Chemistry p. 1237 - 1242 (1983)
Update date:2022-08-04
Topics:
Nakatsuji, Yohji
Nakamura, Tetsuya
Okahara, Mitsuo
Dishong, Dennis M.
Gokel, George W.
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.
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