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Octamethyl-octaundecylcyclo[8]pyrrole:  A Promising Sulfate Anion Extractant

The diprotonated form of an organic-solubilized cyclo[8]pyrrole derivative, bearing eight undecyl chains on the β-pyrrolic positions, was found to extract sulfate anion effectively from neutral aqueous media into a toluene organic phase. The kinetics of sulfate anion exchange between the two phases...

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Published in:Journal of the American Chemical Society 2007-09, Vol.129 (36), p.11020-11021
Main Authors: Eller, Leah R, Stȩpień, Marcin, Fowler, Christopher J, Lee, Jeong Tae, Sessler, Jonathan L, Moyer, Bruce A
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cited_by cdi_FETCH-LOGICAL-a351t-d4c1cc675888333ae55516eb9fd4d75d10cc1553e21ab77d9771fc6e0a223c6d3
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container_end_page 11021
container_issue 36
container_start_page 11020
container_title Journal of the American Chemical Society
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creator Eller, Leah R
Stȩpień, Marcin
Fowler, Christopher J
Lee, Jeong Tae
Sessler, Jonathan L
Moyer, Bruce A
description The diprotonated form of an organic-solubilized cyclo[8]pyrrole derivative, bearing eight undecyl chains on the β-pyrrolic positions, was found to extract sulfate anion effectively from neutral aqueous media into a toluene organic phase. The kinetics of sulfate anion exchange between the two phases were found to be exceedingly slow in the absence of the phase-transfer catalyst, Aliquat 336-nitrate (A336N), but appreciable in its presence. The bisnitrate anion bound form of this cyclo[8]pyrrole could be generated in situ by subjecting the toluene phase containing initially 0.5 mM of the sulfate anion bound form and 0.1 mM trioctylamine (TOA) to successive equilibrations with aqueous 0.1 M HNO3 until sulfate was no longer detected in the aqueous phase. This bisnitrate complex, when studied as a 0.5 mM solution in toluene in the presence of 0.1 mM (TOAH)+(NO3 -), was also found to be an effective extractant for sulfate anion. D SO4 values of 0.001 and 1000 were observed at 1 M NaNO3(aq) and 0.3 mM NaNO3(aq), respectively, and the logarithm of the conditional exchange constant, log( ), was calculated to be 4.9 ± 0.4. The present cyclo[8]pyrrole system is thus noteworthy as being the first synthetic receptor that displays a high selectivity for sulfate anion in the presence of excess nitrate under conditions of solvent extraction.
doi_str_mv 10.1021/ja074568k
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title Octamethyl-octaundecylcyclo[8]pyrrole:  A Promising Sulfate Anion Extractant
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