• Analytical Science and Technology
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• v.20 no.3
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• pp.255-260
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• 2007

A new method for the simultaneous determination of low molecular weight amines and quaternary ammonium ions based on the separation by IC with a suppressor and the detection by MS with ESI has been developed. The method has been applied to the analysis of a mixture containing tetramethylammonium ion, tetraethylammonium ion, tetrapropylammonium ion, triethanolamine, trimethylamine and triethylamine. The constituents were separated by isocratic elution using an IonPac CS17 column, a cation-exchange column, and detected by conductivity and mass spectrometry. The newly developed method for the six components demonstrated that the repeatability in terms of relative standard deviation for three measurements was in the range of 0.1-0.5 %. The detection limits were between 0.2 and $0.9{\mu}g/mL$ by the IC/ESI-MS.

• Bulletin of the Korean Chemical Society
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• v.35 no.1
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• pp.21-22
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• 2014

• Bulletin of the Korean Chemical Society
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• v.28 no.12
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• pp.2299-2302
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• 2007

A series of quaternary ammonium-based ionic liquids (ILs) containing an alkyl carbonate group on the cation was first prepared and their physical and electrochemical properties including density, viscosity, thermal stability, electrochemical stability, and ionic conductivity were reported. These ILs exhibited wide electrochemical windows of at least 5.0 V and relatively high conductivities. In contrast to dialkyl-substituted ionic liquids, the ILs with an alkyl carbonate group on the cation showed much smaller drop in conductivities when mixed with a lithium salt, due to the interaction of lithium ions with carbonate groups. Upon interaction with a Li salt, the carbonyl stretching frequency of the carbonate group shifted to a lower frequency whereas the peak associated with C-O single bond moved to a higher frequency.

• Archives of Pharmacal Research
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• v.29 no.4
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• pp.318-322
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• 2006

Many quaternary ammonium salts are incompletely absorbed after their oral administration and may also be actively secreted into the intestine. However, the underlying mechanism(s) that control the transport of these cations across the intestinal epithelium is not well understood. In this study, the mechanism of absorption of quaternary ammonium salts was investigated using Caco-2 cell monolayers, a human colon carcinoma cell line. Tributylmethylammonium (TBuMA) was used as a model quaternary ammonium salts. When TBuMA was administrated at a dose of 13.3 imole/kg via iv and oral routes, the AUC values were $783.7{\pm}43.6\;and\;249.1{\pm}28.0{\mu}mole\;min/L$ for iv and oral administration, indicating a lower oral bioavailability of TBuMA $(35.6\%)$. The apparent permeability across Caco-2 monolayers from the basal to the apical side was 1.3 times (p<0.05) greater than that from the apical to the basal side, indicating a net secretion of TBuMA in the intestine. This secretion appeared to be responsible for the low oral bioavailability of the compound, probably mediated by p-gp (p-glycoprotein) located in the apical membrane. In addition, the uptake of TBuMA by the apical membrane showed a $Na^+$ dependency. Thus, TBuMA appears to absorbed via a $Na^+$ dependent carrier and is then secreted via p-gp related carriers.

• Bulletin of the Korean Chemical Society
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• v.31 no.8
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• pp.2289-2292
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• 2010

Long chain dicationic ammonium salts were used successfully as phase transfer catalyst in the condensation reactions of aromatic aldehydes in water under ultrasonic irradiation for the first time. The quaternary salt having longer distance between the cation centers was more effective than the mono- and dicationic ones having short chain.

• Analytical Science and Technology
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• v.8 no.4
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• pp.675-682
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• 1995

Thin films of buckminsterfullerene($C_{60}$) formed by solution drop casting on Pt foil electrode surfaces were studied by cyclic voltammetry(CV) in acetonitrile(MeCN) containing quaternary ammonium or alkali-metal salts as supporting electrolyte. The electrochemical behaviors of $C_{60}$ films are found to be strongly dependent on the nature of the supporting electrolytes, especially with tetrabutyl ammonium perchlorate (TBAP, $NBu_4ClO_4$), and tetrabutyl ammonium tetrafluoroborate ($TBABF_4$, $NBu_4BF_4$). Reasonably stable films are formed into which electrons can be injected. The interaction of $C_{60}$ film with the quaternary ammonium cation may produce the fulleride salts $(TBA^+)(C{_{60}}^-)$ and $(TBA^+)_2(C{_{60}}^{2-})$. The bulk electroreduction with a controlled potential to generate the soluble $C{_{60}}^{3-}$ anions(dark red-brown color) is followed by electrooxidative deposition to produce a neutral $C_{60}$ film on the surface. The peak currents($I_{pc}$ and $I_{pa}$) of these thin film were dramatically decreased with repetitive potential scanning. These results could be explained by the adsorption-desorption phenomena and ion pairing interaction of reduced species($C{_{60}}^-$, and $C{_{60}}^{2-}$) onto the electrode surface. The peak current changes and peak potential shifts of the thin $C_{60}$ film in cyclic voltammograms formed from solution were observed by varying scan rates.

• Analytical Science and Technology
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• v.8 no.1
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• pp.33-40
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• 1995

Only trace amounts of hydroxide ion can be extracted from aqueous phase into organic phase by Tetra-n-Butyl Ammonium Chloride(TBAC). Addition of small amounts of primary alcohols, particularly certain dials, dramatically changes the behavior of Phase Transfer Catalysis systems, and surprising amounts of base can be found in the organic phase. Quantitative measurements were carried out for the extraction amounts of primary alkoxides, secondary alkoxides, and diol anions into organic phase. On the other hand, the selectivity constants for extraction of primary alcohols and benzylalcohol could be separated to the equilibrium constants of the ion pairs such as $Q^+RO^-$ and $Q^+Cl^-$ in the aqueous and organic phases and this distribution coefficients between phases on anions respectively. In a word, the colligated property for the selectivity of $Q^+RO^-$ in which $Q^+$ is quaternary cation and $RO^-$ alkoxide ion could be discussed in more detail by using of the corresponding free energies to the various constants mentioned.

• The Korean Journal of Nuclear Medicine
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• v.28 no.3
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• pp.331-337
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• 1994

In order to develop a $^{18}F$-labelled myocardial perfusion agent(flow tracer) for PET, $^{18}F$-labelled organic ammonium cations were synthesized and evaluated in relation to their biodistribution. Five quaternary organic ammonium compounds were labelled with $^{18}F$ in a side chain with moderate to good yields by direct introduction of $^{18}F$-fluoride. Radiochemical yields have been achieved in 30-40min by the precursors (tosylates) in dimethylsulfoxide 15-60% (decay corrected). The reaction was found to be autocatalyzed. A remote controlled procedure was developed in these synthesis. $^{18}F$-Labelling and HPLC-purification of com-pounds needed about 60 min(Yield; 7-20%). Up to now the two compounds N-4-[$^{18}F$]fluorobutyl-pyridinium cation(1) and N, N dibenzyl-4(2-[$^{18}F$]fluoroethyl)piperidinium cation(2) were investigated in relation to their biodistribution in mice. Compound 1 showed at 1 min post injection the high uptake of 19.22% ID/g organ in the myocardium but a following fast decline to 1.12% ID/g organ after 40min. Uptake of compound 2 was after 1min in the heart 5.90% ID/g organ but after 40min at the relative high value of 4.33% ID/g organ. Heart:blood ratio for compound(1) at 1 min was 8.3, at 40 min 2.6 for compound II 2.0(1min) and 15.0(40 min). As data of compound 2 showed greater heart uptake, slower myocardial release, and higher heart: blood ratios, compound 2 is a good candidate for further evaluation.

• Bulletin of the Korean Chemical Society
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• v.34 no.9
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• pp.2616-2622
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• 2013

A novel zwitterionic monomer 3-[(2-acrylamido)dimethylammonio]propanesulfonate (DMADAS) was designed and synthesized in this study. Then it was polymerized with acrylamide (AM) by free radical polymerization in 0.5 mol/L NaCl solution with ammonium persulfate ($(NH_4)_2S_2O_8$) and sodium sulfate ($NaHSO_3$) as initiator. The structure and composition of DMADAS and acrylamide-3-[(2-acrylamido)-dimethylammonio]propanesulfonate copolymer (P-AM-DMADAS) were characterized by FT-IR spectroscopy, $^1H$ NMR and elemental analyses. Isoelectric point (IEP) of P-AM-DMADAS was tested by nanoparticle size and potential analyzer. Solution properties of copolymer were studied by reduced viscosity. Antipolyelectrolyte behavior was observed and was found to be enhanced with increasing DMADAS content in copolymer. The results showed that the viscosity of P-AM-DMADAS is 5.472 dl/g in pure water. Electrolyte was added, which weakened the mutual attraction between sulfonic acid group and quaternary ammonium group. The conformation became loose, which led to the increase of reduced viscosity. The ability of monovalent and divalent cation influencing the viscosity of zwitterionic copolymer obeyed the following sequence: $Li^+$ < $Na^+$ < $K^+$, $Mg^{2+}$ < $Ca^{2+}$ < $Ba^{2+}$, and that of anion is in the order: $Cl^-$ < $Br^-$ < $I^-$, $CO{_3}^{2-}$ > $SO{_3}^{2-}{\approx}SO{_4}^{2-}$.

• Journal of the Korean Society of Food Science and Nutrition
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• v.33 no.9
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• pp.1584-1587
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• 2004

The betaine content of Saliconia herbacea L. was determined by reverse-phase high performance chromatog-raphy on a C_(18) column. A 50% methanol extract was passed through a anion exchanger Ambelite IRA 400 (quaternary ammonium type, OH-) column and a strong cation exchanger Ambelite IR 120 (sulfonic acid type, $H^+$) column to remove amino acids, zwitter ions which are interfere with betaine analysis. The betaine extract was derivatized with 18-crown-6-ether and 4-bromophenacyl bromide (PBPB) for UV-labelling. Betaine in Saliconia herbacea L. was analysed on a mobile phase contained 13 mM sodium heptane sulfonic acid and 5 mM $Na_2SO_4$ in deionized water by isocratic elution for 30 min. The recovery ratio of betaine from Saliconia herbacea L. extract was 83.6%. The mean betaine value for Saliconia herbacea L. determined by the described method is 4.85 mg/mL with a standard deviation of 0.127.