J. Pernak et al.
FULL PAPER
tated in the form of a white sediment, was recrystallized from an EtOAc/
EtOH mixture (10:1, v/v). The final product was obtained as a hygro-
scopic compound and drying required rotary evaporation at ca. 508C/
8 mmHg for 8 h.
Micrococcus luteus ATCC 9341, and Enterococcus hirae ATCC 10541,
and fungi by Candida albicans ATCC 10231 and Rhodotorula rubra
(Demml 1889, Lodder 1934). Standard strains were supplied by the Na-
tional Collection of Type Cultures (NCTC), London, and the American
Type Culture Collection (ATCC). TheR. rubra was obtained from the
collection of the Department of Pharmaceutical Bacteriology, University
1
[(C7Om)2im][Cl]: H NMR (CDCl3): d = 10.85 (s, 1H; CH), 7.75 (d, J =
1.4 Hz, 2H; 2îCH), 5.84 (s, 4H; 2îCH2), 3.61 (t, J = 6.5 Hz, 4H; 2î
CH2), 1.57 (q, J = 6.8 Hz, 4H; 2îCH2), 1.26 (m, 16H; 8îCH2), 0.87 (t,
J = 6.7 Hz, 6H; 2îCH3); 13C NMR (CDCl3): d = 137.4, 121.4, 79.1,
70.5, 31.3, 28.9, 28.6, 25.5, 22.2, 13.7; elemental analysis calcd (%) for
C19H37N2O2Cl (360.97): C 63.22, H 10.33, N 7.76; found: C 63.01, H
10.57, N 7.48.
¬
of Medical Sciences, Poznan, Poland. Antimicrobial activity was deter-
mined by the tube dilution method, as described previously.[31]
QSAR analysis
Structural parameters: The theoretically calculated logarithms of 1-octa-
nol/water partition coefficient parameters (ClogP) were chosen as struc-
tural parameters for the obtained [(CnOm)2im][Cl] ILs. For these chlo-
rides, the parameters (ClogP) were calculated by means of the KOWIN
v.1.66 program (Syracuse Research Corporation, NY, United States)
from EPI Suite software package, v.3.10 (U.S. Environmental Protection
Agency), based on the Meylan Howard method.
Procedure for ion exchange: A saturated aqueous solution of NaBF4 or
KPF6 or LiNTf2 was added to a stoichiometric amount of a saturated hot
aqueous solution of a prepared [(CnOm)2im][Cl]. The reaction mixture
was stirred at room temperature for 2 h affording a heterogeneous mix-
ture. After separation of the phases, the aqueous phase was decanted and
the obtained salt was washed with water until chloride ions were no
longer detected using AgNO3. The prepared salt was dried for 10 h at
808C in vacuum (8 mmHg). For salts soluble in water: The water was re-
moved from the reaction mixture under reduced pressure. Ethyl acetate
was added to the remaining suspension and the organic phase was
washed with water. The volatile materials were removed under reduced
pressure.
Statistics: The statistical analysis was carried out using Statistica v.6 soft-
ware (StatSoft, Inc., Tulsa, OK, United States).
Determination of permanganate index: A sample of 3 mmol of the IL
was heated in boiling water with KMnO4 and H2SO4 for 10 min. The esti-
mations were performed in accordance with the norm (EN
ISO 8467:1995).
[(C6Om)2im][BF4]: 1H NMR (CDCl3, 258C): d = 9.12 (s, 1H; CH), 7.48
(d, J = 1.6 Hz, 2H; 2îCH), 5.91 (s, 4H; 2îCH2), 3.56 (t, J = 6.5 Hz,
4H; 2îCH2), 1.51 (q, J = 6.8 Hz, 4H; 2îCH2), 1.27 (m, 12H; 6îCH2),
0.87 (t, J = 6.7 Hz, 6H; 2îCH3); 13C NMR (CDCl3): d = 135.7, 121.6,
79.5, 70.7, 31.4, 29.1, 25.4, 22.4, 13.9; elemental analysis calcd (%) for
C17H33N2O2BF4 (384.26): C 53.09, H 8.66, N 7.29; found: C 52.81, H 8.97,
N 7.08.
Acknowledgement
This work was supported by the Polish Committee of Scientific Research
under grant No. 4 T09B 008 22.
[(C7Om)2im][PF6]: 1H NMR (CDCl3, 258C): d = 8.79 (s, 1H; CH), 7.48
(d, J = 1.4 Hz, 2H; 2îCH), 5.54 (s, 4H; 2îCH2), 3.54 (t, J = 6.5 Hz,
4H; 2îCH2), 1.57 (q, J = 6.9 Hz, 4H; 2îCH), 1.27 (m, 16H; 8îCH2),
0.87 (t, J = 6.7 Hz, 6H; 2îCH3); 13C NMR (CDCl3): d = 137.4, 121.5,
79.7, 70.9, 31.6, 29.1, 28.9, 25.6, 22.5, 13.9; elemental analysis calcd (%)
for C19H37N2O2PF6 (470.25): C 48.48, H 7.99, N 5.96; found: C 48.11, H
7.57, N 5.88.
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[5] J. Dupont, R. F. de Souza, P. A. Z. Suarez, Chem. Rev. 2002, 102,
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[(C7Om)2im][NTf2]: H NMR (CDCl3, 258C): d = 9.04 (s, 1H; CH), 7.53
(d, J = 1.4 Hz, 2H; 2îCH), 5.57 (s, 4H; 2îCH2), 3.53 (t, J = 6.6 Hz,
4H; 2îCH2), 1.58 (q, J = 6.9 Hz, 4H; 2îCH2), 1.26 (m, 16H; 8îCH2),
0.87 (t, J = 6.6 Hz, 6H; 2îCH3); 13C NMR (CDCl3): d = 135.2, 126.0,
121.8, 121.7, 117.5, 113.3, 79.6, 70.9, 31.7, 29.1, 28.9, 25.7, 22.6, 14.0; ele-
mental analysis calcd (%) for C21H37N3O6F6 (541.26): C 46.56, H 6.89, N
7.76; found: C 46.71, H 6.57, N 7.58.
Preparation of 1-alkoxymethylimidazoles: ROCH2Cl (0.05 mol) was
slowly added to a stirred anhydrous solution of triethylamine (5.06 g,
0.05 mol) in toluene (50 mL), and stirring was continued at 808C for
15 min. Imidazole (3.4 g, 0.05 mol) was then added. After 30 min, the
mixture was refluxed. After cooling to room temperature, the triethyl-
amine hydrochloride produced was filtered off and the toluene was
evaporated. The product was purified by vacuum distillation.
Antielectrostatic properties: The antielectrostatic effect was measured on
a polypropylene film, which was free from lubricants and antioxidants.
From this 0.25 mm film, 12.5 mm diameter disks were cut out. The PP
disks were washed with acetone and then dried by placing them in an air-
conditioned room. The disks were then immersed in 0.5% solutions of
studied chlorides in chloroform for 60 s. After removal from the solution,
each disk was hung up so that the chloroform could evaporate spontane-
ously. The surfaces of the disks were then rubbed with a cotton pad to
ensure complete coverage with the precipitated material. The disks were
stored for 24 h in an air-conditioned room at 20 Æ 28C with a relative
humidity of 60 Æ 5%. Finally, the surface resistance and half-charge
decay times were measured. The measuring apparatus has been described
previously.[16] The relative error in the determination of these two quanti-
ties did not exceed 7%.
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Antimicrobial activity: Eleven standard strains were used: rods were rep-
resented by Pseudomonas aeruginosa ATCC 15442, Escherichia coli
NCTC 8196, Klebsiella pneumoniae ATCC 4352, and Proteus vulgaris
NCTC 4635; cocci by Staphylococcus aureus ATCC 6538, Staphylococcus
aureus MRSA ATCC 43300, Staphylococcus epidermidis ATCC 12228,
3484
¹ 2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Chem. Eur. J. 2004, 10, 3479 3485