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Synthesis and Properties of Novel Cage-Annulated Crown Ethers

Three cage-functionalized polyoxacrown ethers (9, 10 and 12) and four novel cage-functionalized polyoxamonoazacrown ethers (18, 20, 25 and 29) that contain 3,5-disubstituted-4-oxahexacyclo[5.4.0.02,6.03,10.05,9.08,11]dodecane ("oxahexacyclic") moiety have been synthesized and their respective alkali metal picrate extraction profiles along with that of three analogues 13, 14 and 21 have been obtained. The observed avidities and selectivities of the host molecules toward complexation and transport of alkali metal picrates can be related to the size and shape of their respective macrocyclic cavity and the number of donor atoms. The effect of N-alkyl substitution on the complexation properties of azacrown ethers has been studied. The avidity of N-Et azacrown ethers toward complexation with alkali metal cations is generally higher than that of the corresponding non-N-alkylated hosts. However, the presence of an N-Et group appears to have a negligible effect upon their relative selectivities in their regards. The effect of pH on extraction process was studied; it was thereby determined that the alkali metal picrate extraction experiments are best performed at high pH (ca. 11-12).

Identiferoai:union.ndltd.org:unt.edu/info:ark/67531/metadc5523
Date05 1900
CreatorsHuang, Zilin
ContributorsMarchand, Alan P., Dandekar, Sushama
PublisherUniversity of North Texas
Source SetsUniversity of North Texas
LanguageEnglish
Detected LanguageEnglish
TypeThesis or Dissertation
FormatText
RightsUse restricted to UNT Community (strictly enforced), Copyright, Huang, Zilin, Copyright is held by the author, unless otherwise noted. All rights reserved.

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