Trigeminal Tricationic Ionic Liquids
FULL PAPER
1,2,3-Propanetri[oxymethyl-1-(3-vinylimidazolium)] bis(trifluoromethane-
sulfonyl)imide (1 f): 1H NMR (300 MHz, CD3CN, 258C, TMS): d=8.88
(m, 3H), 7.79 (m, 3H), 7.62 (m, 3H), 7.21 (m, 3H), 5.88 (m, 4H), 5.63 (s,
2H), 5.50 (m, 6H), 3.99 (m, 1H), 3.68 ppm (m, 4H); 13C NMR (75 MHz,
CD3CN, 258C, TMS): d=135.6, 135.5, 129.3, 127.2, 123.4, 123.3, 122.9,
121.0, 120.7, 118.7, 118.4, 114.4, 111.1, 111.0, 80.3, 79.7, 78.2, 70.3 ppm; el-
emental analysis calcd (%) for C27H29O15N9S6F18: C 25.86, H 2.33, N
10.05; found: C 26.03, H 2.54, N 10.42.
308C (fungi). The lowest concentration of the substances that kills 99.9%
or more of the test organism was defined as the MBC.
Electrochemical measurements: All the electrochemical investigations
were performed by using pure TTILs without any additional solvent. The
decomposition potential for all the TTILs was estimated by means of
linear sweep voltammetry at 5 mVsÀ1 on two polycrystalline gold electro-
des in which an Ag/Ag+ electrochemical system served as the reference
electrode.
1,2,3-Propanetri[oxymethyl-1-(3-carbamoylpyridinium)] bis(trifluorome-
thanesulfonyl)imide (2c): 1H NMR (300 MHz, CD3CN, 258C, TMS): d=
9.42 (s, 1H; arom.), 9.23 (s, 2H; arom.), 8.91 (d, J=1.5 Hz, 1H; arom.),
8.90 (d, J=1.5 Hz, 1H; arom.), 8.89 (d, J=6 Hz, 4H; arom.), 8.23 (t, J=
7 Hz, 3H; arom.), 7.44 (s, 1H; NH), 7.39 (s, 2H; 2NH), 6.82 (s, 1H;
NH), 6.80 (s, 2H; 2NH), 6.05 (s, 2H; OCH2N), 5.84 (q, J=9.3 Hz, 4H;
2OCH2N), 4.19 (m, 1H; CH), 3.86 ppm (m, 4H; 2OCH2CH); 13C NM R
(75 MHz, CD3CN, 258C, TMS): d=164.0, 163.6, 146.3, 146.2, 145.4, 143.9,
135.2, 134.9, 129.3, 129.0, 122.9, 118.6, 118.3, 90.1, 89.3, 79.7, 71.0 ppm; el-
emental analysis calcd (%) for C30H29O18N9S6F18: C 26.93, H 2.18, N 9.42;
found: C 26.75, H 2.03, N 9.63.
Conductivity measurements were based on impedance spectroscopy in
which the complex resistivities are generated by using the ac current am-
plitude. The resistivity of a system, without considering diffusion, was cal-
culated by using Ohmꢁs law. For capacitance measurements, NORIT acti-
vated carbon was used, which had a specific surface area of 2070 m2 gÀ1
and an external surface area of 374 m2 gÀ1. Voltammetry, galvanostatic,
and impedance spectroscopy experiments were performed with a two-
electrode Swagelok system to estimate capacitance values expressed in
FgÀ1 per electrode. All the electrochemical measurements were per-
formed by using a potentiostat-galvanostat VMP/2Z instrument (BIO-
LOGIC, France).
1,2,3-Propanetri[oxymethyl-1-(3-carbamoylpyridinium)] tetrafluoroborate
(2d): 1H NMR (300 MHz, D2O, 25 8C, TMS): d=9.54 (s, 1H), 9.36 (s,
2H), 9.09 (m, 6H), 8.31 (m, 3H), 6.17 (s, 4H), 5.97 (s, 2H), 4.82 (s, 6H),
4.36 (m, 1H), 3.91 ppm (m, 4H); 13C NMR (75 MHz, D2O, 25 8C, TMS):
d=168.1, 148.4, 148.3, 147.8, 147.5, 145.8, 145.5, 136.7, 131.2, 130.9, 92.1,
91.5, 81.8, 72.8 ppm; elemental analysis calcd (%) for C24H29O6N6F12B3:
C 38.03, H 3.86, N 11.09; found: C 38.24, H 3.65, N 10.95.
Acknowledgement
This work was supported by Polish Committee of Scientific Research
under grant no. PBZ-KBN-101/T03/2003.
1,2,3-Propanetri[oxymethyl-1-(4-dimethylaminopyridinium)] bis(trifluoro-
methanesulfonyl)imide (2e): 1H NMR (300 MHz, CD3CN, 258C, TMS):
d=8.01 (m, 6H), 7.95 (d, J=9 Hz, 2H), 7.94 (d, J=8 Hz, 4H), 6.89 (d,
J=8 Hz, 4H), 6.84 (d, J=9 Hz, 2H), 5.40 (s, 2H), 5.28 (s, 4H), 3.87 (m,
1H), 3.54 (m, 4H), 3.214 (s, 12H), 3.208 ppm (s, 6H); 13C NM R
(75 MHz, CD3CN, 258C, TMS): d=158.1, 141.7, 141.5, 127.1, 122.9, 118.6,
118.1, 114.4, 108.4, 108.1, 88.6, 86.0, 78.0, 69.8, 40.8 ppm; elemental analy-
sis calcd (%) for C33H41O15N9S6F18: C 29.61, H 3.09, N 9.42; found: C
29.81, H 3.25, N 9.07.
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Antimicrobialactivities : Standard strains were supplied by the National
Collection of Type Cultures (NCTC) London, the American Type Cul-
ture Collection (ATCC), and R. rubra was obtained from the Depart-
ment of Pharmaceutical Bacteriology, University of Medical Sciences,
´
Poznan. The following microorganisms were used: Micrococcus luteus
NCTC 7743, Staphylococcus aureus NCTC 4163, Staphylococcus epider-
midis ATCC 49134, Enterococcus faecium ATCC 49474, Moraxella catar-
rhalis ATCC 25238, Escherichia coli ATCC 25922, Serratia marcescens
ATCC 8100, Proteus vulgaris NCTC 4635, Pseudomonas aeruginosa
NCTC 6749, Bacillus subtilis ATCC 6633, Candida albicans ATCC 10231,
and Rhodotorula rubra (Demml 1889, Lodder 1934).
Antimicrobial activity was determined by means of tube dilution meth-
ods. Bacterial strains were cultured by using a Müller–Hinton broth, and
fungi were cultured on Sabouraud agar. The suspensions of standard mi-
croorganisms, at a concentration of 106 cfumLÀ1 (cfu=colony forming
units), were prepared from each culture. Samples (2 mL) of the com-
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dized suspension of test microorganism to obtain a final concentration of
1–5105 cfumLÀ1. The growth (or lack thereof) of the microorganism
was determined visually after incubation for 24 h at 378C (bacteria) or
48 h at 28–308C (fungi). The lowest concentration at which there was no
visible growth (turbidity) was taken as the MIC. An aliquot was then
taken from each tube in a sample loop, was cultured in agar medium
with inactivates (lecithin (0.3%), polysorbate 80 (3%), and l-cysteine
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