In conclusion we have demonstrated that two different classes
of ionic liquid chelate complexes can be prepared from a common
precursor, 2, that is derived from comparatively less expensive
starting materials than other chelating ionic liquids that have
appeared in the literature. Whereas the IL-bis(oxime)-Cu chelate
complex, 4, is related to oxime complexes used in the hydromet-
group P2(1)/c; unit cell dimensions: a = 8.492(4) A˚ , b = 10.988(5) A˚ ,
◦
3
b = 91.442(12) , c = 35.208(17) A˚ ; volume = 3284(3) A˚ ; Z = 4; density
−
3
−1
(
1
1
calculated) = 1.703 Mg m ; absorption coefficient = 0.875 mm ; F(000)
700; crystal size 0.35 × 0.20 × 0.10 mm; theta range for data collection
◦
.16 to 25.23 ; index ranges −7 ≤ h ≤ 10, −10 ≤ k ≤ 12, −42 ≤
II
l ≤ 36; reflections collected = 12988; independent reflections = 5754
◦
[
R(int) = 0.1029]; completeness to theta = 25.23 , 96.9%; absorption
correction semi-empirical from equivalents; max. and min. transmission
allurgical refinement of copper it has great promise in such an
2
1
.000 and 0.480; refinement method = full-matrix least-squares on F ;
II
2
application. Given the excellent solubility of the IL-salen-Cu
data/restraints/parameters 5754/0/462; goodness-of-fit on F = 1.106;
final R indices [I>2r(I)], R1 = 0.1151, wR2 = 0.2477; R indices (all
III
complex, 5, and IL-salen-Mn -Cl, 6, in various ionic liquids
data) R1 = 0.2015, wR2 = 0.2935; largest diff. peak and hole 0.896 and
commonly used in catalytic applications it is likely that complexes
containing the IL-salen ligand will have great potential for use
in such instances. It is antipicated that a number of other metals
can be incorporated into IL-salen-metal complexes of this class
and that these could be immobilized in ionic liquid solvents to a
greater extent than traditional catalysts.
We are actively pursuing the ability of the IL-bis(oxime)-
metal complexes to extract metals from aqueous systems and
are applying the use of the IL-salen-metal complexes in catalytic
applications. Details of these studies will be a topic of forthcoming
full accounts.
0.555 e A˚ −
3
−
.
1
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Acknowledgements
5
6
P. Majewski, A. Pernak, M. Grzymisławski, K. Iwanik and J. Pernak,
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We would like to acknowledge the Natural Sciences and Engi-
neering Research Council of Canada (NSERC) for funding this
research through a Discovery grant to R. D. S. and a Research
Capacity Development Grant to Saint Mary’s University (SMU-
FGSR), and the Nova Scotia Office for Economic Development.
Ionic Liquids in Synthesis, ed. Peter Wasserscheid and Thomas
Welton, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2nd edn,
2
008.
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Notes and references
II
‡
Crystal data and structure refinement for IL-bis(oxime)-Cu chelate
complex, 4. Empirical formula C24
6 4 2
H26CuF12N O P ; formula weight
8
15.99; temperature 100(2) K; wavelength 0.71073 A˚ ; crystal system:
¯
˚
triclinic; space group P1; unit cell dimensions a = 10.115(4) A, a =
◦
◦
7
0.115(8) , b = 18.066(7) A˚ , b = 85.613(8) ; c = 18.153(6) A˚ , c =
◦
3
7
m
4.682(7) ; volume 3008.5(19) A˚ ; Z = 4; density (calculated) 1.802 Mg
−
3
−1
; absorption coefficient 0.952 mm ; F(000) 1644; crystal size 0.20 ×
9 A. E. Visser, R. P. Swatloski, W. M. Reichert, R. Mayton, S. Sheff, A.
Wierzbicki, J. H. Davis, Jr. and R. D. Rogers, Chem. Commun., 2001,
135; S. Lee, Chem. Commun., 2006, 1049.
10 J. R. Harjani, T. Fri sˇ cˇ i c´ , L. R. MacGillivray and R. D. Singer, Inorg.
Chem., 2006, 45, 10025.
11 Provisional Patent US 61/032 103 filed on February 28, 2008.
12 A. Dalla Cort, L. Mandolini, C. Pasquini and L. Schiaffino, Org.
Biomol. Chem., 2006, 4, 4543.
13 N. Ackerley and P. A. Mack (Imperial Chemical Industries Ltd.),
Extraction of metals from aqueous solutions, Ger. Pat., 2 313 192,
1973.
◦
0
.15 × 0.10 mm; theta range for data collection 1.19 to 28.31 ; index
ranges −13 ≤ h ≤ 13, −23 ≤ k ≤ 20, −20 ≤ l ≤ 23; reflections collected =
1
7 825; independent reflections = 13 69 [R(int) = 0.0544]; completeness
◦
to theta = 26.00 , 97.1%; refinement method = full-matrix least-squares
2
2
on F ; data/restraints/parameters 13069/0/891; goodness-of-fit on F =
0
.965; final R indices [I>2r(I)] R1 = 0.0802, wR2 = 0.1615; R indices (all
data): R1 = 0.1574, wR2 = 0.2037; largest diff. peak and hole = 0.906 and
0.735 e A˚ −
3
−
.
II
§
Crystal data and structure refinement for IL-salen-Cu chelate complex,
. Empirical formula C26 ; formula weight 842.02; temper-
5
6 4 2
H28CuF12N O P
ature 100(2) K; wavelength 0.71073 A˚ ; crystal system: monoclinic; space
14 C. E. Song and E. J. Roh, Chem. Commun., 2000, 837.
4
836 | Dalton Trans., 2008, 4834–4836
This journal is © The Royal Society of Chemistry 2008