NDLI: Mercury(ii) partitioning from aqueous solutions with a new, hydrophobic ethylene-glycol functionalized bis-imidazolium ionic liquid

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Mercury(ii) partitioning from aqueous solutions with a new, hydrophobic ethylene-glycol functionalized bis-imidazolium ionic liquid

Content Provider	Royal Society of Chemistry (RSC)
Author	Swatloski, Richard P. Broker, Grant A. Rogers, Robin D. Holbrey, John D. Reichert, W. Matthew Visser, Ann E. Spear, Scott K.
Copyright Year	2003
Abstract	A room temperature ionic liquid containing a bis-imidazolium cation incorporating a short ethylene-glycol spacer, 1,1′-[1,2-ethanediylbis(oxy-1,2-ethanediyl)] bis[3-methyl-1H-imidazolium-1-yl]bis(trifluoromethanesulfonyl)imide, has been prepared from the corresponding chloride salt, and the X-ray crystal structure of the low-melting hexafluorophosphate salt has been determined. The crystal structure reveals the ether linkage to be quite flexible and to participate in strong C2–H⋯O hydrogen bonds leading to asymmetry. The crystal structure of the bis-imidazolium salt incorporating a decyl-spacer, 1,1′-[1,10-decyl]bis[3-methyl-1H-imidazolium-1-yl] hexafluorophosphate, has also been determined and displays an all-trans (symmetric) conformation except at the beta carbon positions where a characteristic kink is observed. Introducing the ethylene-glycol functionality dramatically increases the distribution ratio of mercury ions, but not caesium, from aqueous solution to the hydrophobic ionic liquid, and from basic solution. This is the first example of pH dependent partitioning and stripping of mercury from ionic liquid/aqueous two-phase systems. The crystal structure of the related mercury(II) carbene complex, obtained from the reaction of mercury(II) acetate with 1,1′-[oxybis(2,1-ethanediyloxy-2,1-ethanediyl)]bis[3-methyl-1H-imidazolium-1-yl] tosylate, containing a three-ether spacer, in acetonitrile, reveals the possibility of a carbene extraction mechanism.
Starting Page	129
Ending Page	135
Page Count	7
File Format	HTM / HTML PDF
ISSN	14639262
Volume Number	5
Issue Number	2
Journal	Green Chemistry
DOI	10.1039/b300971h
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Ionic liquid Ion Imide Chloride X-ray crystallography Hexafluorophosphate Ether Hydrogen bond Conformational isomerism Alpha and beta carbon Mercury-vapor lamp Caesium Hydrophobe Acid Mercury (element) Transition metal carbene complex Mercury(II) acetate Tosyl Acetonitrile Carbene
Content Type	Text
Resource Type	Article
Subject	Environmental Chemistry Pollution

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