Simple guanidinium motif for the selective binding and extraction of sulfate

Charles A. Seipp; Neil J. Williams; Vyacheslav S. Bryantsev; Bruce A. Moyer

doi:10.1080/01496395.2017.1318922

Simple guanidinium motif for the selective binding and extraction of sulfate

Charles A. Seipp, Neil J. Williams, Vyacheslav S. Bryantsev, Bruce A. Moyer

Chemical Separations Group

Research output: Contribution to journal › Article › peer-review

14 Scopus citations

Abstract

It is shown that a simple guanidinium molecule binds sulfate selectively in methanol/water solution, and a synthesized lipophilic analog permits the selective extraction of sulfate from aqueous sodium chloride into 1,2-dichloroethane. This receptor, N,N’-bis(2-pyridyl)guanidinium, features a rigid pseudo-bicyclic conformation in binding anions in the solid state. It selectively binds sulfate in 10% water/90% MeOD-d₄ solutions with stepwise log K₁ and log K₂ values of 3.78 ± 0.12 and 2.10 ± 0.23, respectively. Density functional theory calculations were performed to predict the conformational preferences of guanidinium receptors upon anion coordination in solution.

Original language	English
Pages (from-to)	1864-1873
Number of pages	10
Journal	Separation Science and Technology (Philadelphia)
Volume	53
Issue number	12
DOIs	https://doi.org/10.1080/01496395.2017.1318922
State	Published - Aug 13 2018

Funding

This research was sponsored by the U.S. Department of Energy, Office of Science, Basic Energy Sciences, Chemical Sciences, Geosciences, and Biosciences Division. This research used resources of the National Energy Research Scientific Computing Center, a DOE Office of Science User Facility supported by the Office of Science of the U.S. Department of Energy under contract number DE-AC02-05CH11231.

Keywords

Guanidinium
anion binding
density functional theory
extraction
sulfate

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10.1080/01496395.2017.1318922

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abstract = "It is shown that a simple guanidinium molecule binds sulfate selectively in methanol/water solution, and a synthesized lipophilic analog permits the selective extraction of sulfate from aqueous sodium chloride into 1,2-dichloroethane. This receptor, N,N{\textquoteright}-bis(2-pyridyl)guanidinium, features a rigid pseudo-bicyclic conformation in binding anions in the solid state. It selectively binds sulfate in 10% water/90% MeOD-d4 solutions with stepwise log K1 and log K2 values of 3.78 ± 0.12 and 2.10 ± 0.23, respectively. Density functional theory calculations were performed to predict the conformational preferences of guanidinium receptors upon anion coordination in solution.",

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AU - Williams, Neil J.

AU - Bryantsev, Vyacheslav S.

AU - Moyer, Bruce A.

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AB - It is shown that a simple guanidinium molecule binds sulfate selectively in methanol/water solution, and a synthesized lipophilic analog permits the selective extraction of sulfate from aqueous sodium chloride into 1,2-dichloroethane. This receptor, N,N’-bis(2-pyridyl)guanidinium, features a rigid pseudo-bicyclic conformation in binding anions in the solid state. It selectively binds sulfate in 10% water/90% MeOD-d4 solutions with stepwise log K1 and log K2 values of 3.78 ± 0.12 and 2.10 ± 0.23, respectively. Density functional theory calculations were performed to predict the conformational preferences of guanidinium receptors upon anion coordination in solution.

KW - Guanidinium

KW - anion binding

KW - density functional theory

KW - extraction

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Simple guanidinium motif for the selective binding and extraction of sulfate

Abstract

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