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Title: Simple guanidinium motif for the selective binding and extraction of sulfate

Journal Article · · Separation Science and Technology

A simple bidentate anion receptor, shown previously to adopt a rigid pseudobicyclic conformation while binding anions in the solid state, selectively binds sulfate in aqueous solutions with log K1 and log K2 values of 3.78 ± 0.12 M-1 and 2.10 ± 0.23 M-1, respectively. This anion receptor has little to no affinity for nitrate and chloride in the same solutions. A lipophilic derivative was synthesized in four steps to yield an extractant that is capable of partitioning sulfate into 1,2 dichloroethane from water in the presence of large excesses of chloride. This extractant demonstrated D values as high as 2.5 with only 30 mM of anion receptor.

Research Organization:
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
Sponsoring Organization:
USDOE
Grant/Contract Number:
AC05-00OR22725
OSTI ID:
1408027
Journal Information:
Separation Science and Technology, Vol. 53, Issue 12; ISSN 0149-6395
Publisher:
Taylor & FrancisCopyright Statement
Country of Publication:
United States
Language:
English
Citation Metrics:
Cited by: 8 works
Citation information provided by
Web of Science

References (28)

Anion binding with urea and thiourea derivatives journal July 2015
Enhanced Anion Exchange for Selective Sulfate Extraction: Overcoming the Hofmeister Bias journal November 2008
A conformationally persistent pseudo-bicyclic guanidinium for anion coordination as stabilized by dual intramolecular hydrogen bonds journal January 2015
Molecular recognition of oxoanions based on guanidinium receptors journal January 2007
Anion Partitioning and Ion-Pairing Behavior of Anions in the Extraction of Cesium Salts by 4,5‘ ‘-Bis( tert -octylbenzo)dibenzo-24-crown-8 in 1,2-Dichloroethane journal January 2007
A Case for Molecular Recognition in Nuclear Separations: Sulfate Separation from Nuclear Wastes journal June 2012
α,α′,α″,α′″- meso -tetrahexyltetramethyl-calix[4]pyrrole: an easy-to-prepare, isomerically pure anion extractant with enhanced solubility in organic solvents journal October 2015
Urea-functionalized crystalline capsules for recognition and separation of tetrahedral oxoanions journal January 2013
Ion Pairing journal November 2006
Artificial Organic Host Molecules for Anions journal August 1997
Nuclear Magnetic Resonance as a Tool for Determining Protonation Constants of Natural Polyprotic Bases in Solution journal November 1995
Determining association constants from titration experiments in supramolecular chemistry journal January 2011
Selective Nitrate Binding in Competitive Hydrogen Bonding Solvents: Do Anion-π Interactions Facilitate Nitrate Selectivity? journal August 2013
Zwitterionic Guanidinium Compounds Serve as Electroneutral Anion Hosts journal November 1999
A C 3 Symmetric Nitrate Complex with a Thiophene-Based Tripodal Receptor journal April 2011
The Binding of Sulfate Anions by Guanidinium Receptors is Entropy-Driven journal October 1998
Dipyridyl-Guanidin und seine Derivate journal January 1934
Quantum Mechanical Continuum Solvation Models journal August 2005
Selectivity Control in Synergistic Liquid–Liquid Anion Exchange of Univalent Anions via Structure-Specific Cooperativity between Quaternary Ammonium Cations and Anion Receptors journal September 2012
Cubic, Hydrogen-Bonded (10,3)-a Networks in the Family [C(NH2)3][N(CH3)4][XO4] (X=S, Cr, and Mo) journal November 2004
Structural Investigations of the Phase Transitions of Tetramethylammonium Sulfate journal August 1998
Long-range corrected hybrid density functionals with damped atom–atom dispersion corrections journal January 2008
Cubic, Hydrogen-Bonded (10,3)-a Networks in the Family [C(NH2)3][N(CH3)4][XO4] (X=S, Cr, and Mo) journal November 2004
Selective Nitrate Binding in Competitive Hydrogen Bonding Solvents: Do Anion-π Interactions Facilitate Nitrate Selectivity? journal August 2013
Quantum Mechanical Continuum Solvation Models journal October 2005
Supramolecular Chemistry journal January 2002
Molecular Recognition of Oxoanions Based on Guanidinium Receptors journal May 2007
Supramolecular Chemistry journal May 2005

Cited By (1)

Ion-pair induced supramolecular assembly formation for selective extraction and sensing of potassium sulfate journal January 2019


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