cas 7098-07-9, 1-Ethylimidazole | Articles data

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Solubility of 1-alkyl-3-ethylimidazolium-based ionic liquids in water and 1-octanol
The liquid-liquid phase equilibria (LLE) of the following imidazolium ionic liquids (ELs), {1-ethyl-3-ethylimidazolium, or 1-butyl-3-ethylimidazolium, or 1-hexyl-3-ethylimidazolium bis{trifluoromethyl)sylfonyl}imide [EEIM][Tf 2N], or [BEIM][Tf2N], or [HEIM][Tf2N], + water or + 1-octanol), and {1-butyl-3-ethylimida-zolium hexafluorophosphate [BEEM][PF6] + water or + 1-octanol}, have been measured. The effect of anion type ([Tf2N]- compared to [PF6]-) and the effect of structural components of an ionic liquid including alkyl chain length on the cation and the ethyl substituent instead of methyl at the cation on the physical-chemical properties of the EL and on the phase behavior were studied. An upper critical solution temperature (UCST) was observed in every system. An increase in me alkyl chain length increases the mutual solubility with 1-octanol and partly with water. Ionic liquids with the ethyl substituent on the cation [HEEM][Tf2N] show higher solubility in 1-octanol in comparison wim the methyl substituent. After the synthesis, the characterization and purity of the compounds were obtained by nuclear magnetic resonance (NMR), elemental analysis, water content (Fischer mediod), and differential scanning microcalorimetry (DSC). From DSC, the melting point, enthalpy of fusion, and the temperatures of glass transition of all the investigated ionic liquids were determined. The experimental LLE data were correlated by means of the NRTL equation.
Domanska, Urszula,Rekawek, Anna,Marciniak, Andrzej
p. 1126 - 1132
(2008)
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Identification of radical structures on 1-pentamethylbenzyl-3-ethylimidazoliumsilver(I)bromide and 1,3-bis(pentamethylbenzyl)-4,5-dimethylbenzimidazoliumsilver(I)bromide exposed to gamma rays: an EPR study
1-Pentamethylbenzyl-3-ethylimidazoliumsilver(I)bromide and 1,3-bis(pentamethylbenzyl)-4,5dimethylbenzimidazoliumsilver(I)bromide and their Ag+ complexes were synthesized and their polycrystal forms were produced by recrystallization in dichloromethane/Et2O solvent system. Structural determinations were carried out by 1H NMR and 13C NMR with a Varian 400 NMR system using tetramethylsilane as internal standard and CDCl3 as solvent. The disappearance of acidic N-heterocyclic carbene proton showed the formation of Ag(I) complexes. Also, elemental analyses were carried out. Electron paramagnetic resonance (EPR) measurements were performed to determine the formed radical structure on the samples irradiated at the room temperature for 72 h by using 60Co-source with dose rate of 0.680 kGy. The EPR measurements were carried out in the temperature range of 200 K–450 K. Identical radicals were determined on the irradiated compounds. It was observed that the shapes of the spectra of the samples were independent of the temperature but, the resonance line intensities changed linearly with the temperature. Also, it was detected that the free radical on the 1-pentamethylbenzyl-3-ethylimidazoliumsilver(I)bromide is not stable compared to that on the 1,3-bis(pentamethylbenzyl)-4,5dimethylbenzimidazoliumsilver(I)bromide. Copyright
Ceylan, Yusuf,Usta, Keziban,Kunduracioglu, Ahmet,Usta, Ayhan,Cetinkaya, Bekir
p. 864 - 869
(2016)
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A solventless route to 1-ethyl-3-methylimidazolium fluoride hydrofluoride, [C2mim][F]·xHF
(Chemical Equation Presented) The ionic liquid 1-ethyl-3-methylimidazolium fluoride hydrofluoride, [C2mim][F]·xHF, has been synthesized through a new, solventless route that excludes halogen metathesis. The byproducts are salts, alcohols, and carbon dioxide.
Rijksen, Christiaan,Rogers, Robin D.
p. 5582 - 5584
(2008)
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Influence of the N-N Coligand: C-C coupling instead of formation of imidazol-2-yl complexes at {Mo(η3-allyl)(CO)2} fragments. theoretical and experimental studies
New N-methylimidazole (N-MeIm) complexes of the {Mo(η3-allyl)(CO)2(N-N)} fragment have been prepared, in which the N,N-bidentate chelate ligand is a 2-pyridylimine. The addition of a strong base to the new compounds deprotonates the central CH group of the imidazole ligand and subsequently forms the C-C coupling product that results from the nucleophilic attack to the imine C atom. This reactivity contrasts with that previously found for the analogous 2,2′-bipyridine compounds [Mo(η3-allyl)(CO)2(bipy)(N-RIm)]OTf [N-RIm = N-MeIm, N-mesitylimidazole (N-MesIm, Mes= 2,4,6-trimethylphenyl); OTf = trifluoromethanesulfonate) which afforded imidazol-2-yl complexes upon deprotonation. Density Functional Theory (DFT) computations uncover that the reactivity of the imine C atom along with its ability to delocalize electron density are responsible for the new reactivity pattern found for the kind of molybdenum complexes reported herein.
Cebollada, Andrea,Viguri, Maialen Espinal,Pérez, Julio,Díaz, Jesús,López, Ramón,Riera, Lucía
p. 2580 - 2590
(2015)
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On the effects of head-group volume on the adsorption and aggregation of 1-(n-hexadecyl)-3-Cm-imidazolium bromide and chloride surfactants in aqueous solutions
The effects of the length of alkyl side chain (Cm) of ionic liquid-based surfactants (ILBSs) on their adsorption at the water/air interface, and aggregation in aqueous solutions were investigated for the series 1-(n-hexadecyl)-3-Cm-imidazolium bromides and chlorides, where Cm = C1-C4 for the bromides, and C1-C5 for the chlorides. These physicochemical properties were calculated from surface tension, conductivity, and fluorescence data. It was found that increasing the length of Cm (i.e., volume of the head group) leads to enhancement of surface activity, increase in the area per surfactant molecule at the water/air interface (Amin) and the degree of counter-ion dissociation (αmic). Our data also indicated that increasing the volume of the head group results in a decrease of the critical micelle concentration (cmc), Gibb's free energy of adsorption and micellization, and microscopic polarity of interfacial water. In order to delineate the effects of the presence of unsaturation in the HG, we included members that carry Cm = vinyl and allyl in the bromide series. The effect of these groups was found to be similar to removing a methylene group from Cm. The dependence of the solubilization of a lipophilic dye (Sudan IV) and a drug (nitrendipine) on the length of Cm was also studied.
Keppeler, Nicolas,Galgano, Paula D.,da Silva Santos, Soraya,Malek, Naved I.,El Seoud, Omar A.
(2021/02/09)

Ambient Hydrogenation and Deuteration of Alkenes Using a Nanostructured Ni-Core–Shell Catalyst
A general protocol for the selective hydrogenation and deuteration of a variety of alkenes is presented. Key to success for these reactions is the use of a specific nickel-graphitic shell-based core–shell-structured catalyst, which is conveniently prepared by impregnation and subsequent calcination of nickel nitrate on carbon at 450 °C under argon. Applying this nanostructured catalyst, both terminal and internal alkenes, which are of industrial and commercial importance, were selectively hydrogenated and deuterated at ambient conditions (room temperature, using 1 bar hydrogen or 1 bar deuterium), giving access to the corresponding alkanes and deuterium-labeled alkanes in good to excellent yields. The synthetic utility and practicability of this Ni-based hydrogenation protocol is demonstrated by gram-scale reactions as well as efficient catalyst recycling experiments.
Beller, Matthias,Feng, Lu,Gao, Jie,Jackstell, Ralf,Jagadeesh, Rajenahally V.,Liu, Yuefeng,Ma, Rui
supporting information
p. 18591 - 18598
(2021/06/28)

N-Alkylation of Imidazoles with Dialkyl and Alkylene Carbonates
Abstract: The reactions of imidazoles with a series of dialkyl and alkylene carbonatesafforded the corresponding N-alkyl- andN-(hydroxyalkyl)imidazoles with highyields. The reactivity of dialkyl carbonates decreases in the series dimethyl> diethyl > dibutyl carbonate. Ethylene carbonate is a more efficientalkylating agent than trimethylene carbonate. The mechanisms of alkylation ofimidazole with dimethyl carbonate and ethylene carbonate were studied by DFTquantum chemical calculations at the B3LYP/6-311++G(d,p) level of theory.
Gabov,Khamidullina,Puzyrev,Ezhikova,Kodess,Pestov
p. 2079 - 2086
(2021/02/09)

A 2 - mercapto - 1 - alkyl imidazole of preparation method (by machine translation)
The invention discloses a 2 - mercapto - 1 - alkyl imidazole synthesis method, which belongs to the technical field of organic synthesis. Imidazole and alkyl halide in the presence of an inorganic base sealing reaction the temperature of the 1 - alkyl imidazole, then dissolved in ether in the solvent, the low temperature by adding 1 - 1.1 equivalent BuLi, then adding 0.9 - 0.95 equivalent powder reflux reaction, after cooling add acetyl chloride to obtain 2 - acetyl thio - 1 - alkyl imidazole; the final 2 - acetyl thio - 1 - alkyl imidazole dissolved in alcohol solvent, adding a catalytic amount of hydrogen chloride or potassium carbonate deprotection, to obtain 2 - mercapto - 1 - alkyl imidazole. The raw material of the invention is cheap, and more friendly to the environment, the advantages of easy operation, the quality of the product in accordance with the electronic chemicals using standard. (by machine translation)
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Paragraph 0042; 0043

(2018/01/19)

DERIVATIVES OF IMIDAZOLE AND BENZIMIDAZOLE, METHOD OF PREPARATION AND USE THEREOF
The present invention provides derivatives of imidazole and benzimidazole based thiones and selones used for degrading various toxic heavy metal and salts thereof to a less toxic, stable and insoluble form. The present invention also provides the process of preparation of the said derivatives of imidazole and benzimidazole based thiones and selones and method of detoxification and degradation of various heavy metals including mercury in particular organomercurials, lead, arsenic, cadmium, copper and salts thereof using the said imidazole and benzimidazole-based thione and selone derivatives. The said derivatives have better degradation activity under physiologically and environmentally relevant conditions as well as greater acceptability in a wide range of bases.
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(2017/11/03)

Convenient synthesis of imidazolium based dicationic ionic liquids
A series of imidazolium based Dicationic Ionic Liquids (ILs) have been prepared and characterized successfully. Derivatives are prepared keeping the alkyl chain of alkylimidazole as methyl, ethyl, and propyl groups and the linker dibromoalkane is varied as an ethyl, propyl and butyl group. The variations of anions like Br?, BF4 ? and PF6 ? impact their morphological appearance like amorphous powder to low melting white solids or a hygroscopic nature. Refluxing the alkylimidazoles and dibromoalkanes in toluene for 24?h and an easy workup procedure makes this methodology more time saving for detailed exploration of Dicationic ILs. The formation of dicationic ILs with their anions like Br?, BF4 ?, PF6 ? has been confirmed with 1H, 13C, 31P and 19F NMR spectroscopy as well as the High Resolution Mass Spectroscopy Electron Impact technique.
Aher, Sainath Babaji,Bhagat, Pundlik Rambhau
p. 5587 - 5596
(2016/06/01)

Synthesis, crystal structures and blue emission of zinc(II) halide complexes of 1-alkyl-imidazole and (-)-nicotine
Zn(II) halide complexes of the form L2ZnX2 (X =Cl, Br, I) containing bio-relevant or bio-related ligands like 1-alkyl-imidazoles (alkyl=methyl, ethyl and iso-propyl) or (-)-nicotine are presented. All complexes were characterized by 1H NMR spectroscopy, mass spectrometry and elemental analysis. The molecular structures of the majority of complexes were determined by single crystal X-ray diffraction. The zinc ion exists in a tetrahedral environment coordinated by two halide anions and two nitrogen atoms of the N-heterocycles. Upon photoexcitation the nicotine complexes feature a blue emission which we tentatively assign to phosphorescence.
Hobbollahi, Elnaz,Veselkova, Barbora,List, Manuela,Redhammer, Günther,Monkowius, Uwe
p. 1269 - 1277
(2016/12/09)

1,2,3-Triazolylidene ruthenium(ii)-cyclometalated complexes and olefin selective hydrogenation catalysis
Silver(i) 1,2,3-triazol-5-ylidenes [(RCH2C2N2(NMe)Ph)2Ag][AgCl2] (R = Ph 3a, C6H2iPr33b, C6H2Me33c) and [(PhCH2C2N2(NMe)R)2Ag][AgCl2] (R = C6H4Me 3d, C6H4CF33e) were synthesized and subsequently treated with RuHCl(PPh3)3 and RuHCl(H2)(PCy3)2. The reaction of 3a with RuHCl(PPh3)3 gave RuHCl(PPh3)2(PhCH2C2N2(NMe)Ph) (4a1) as the minor product and the cyclometalated complex RuCl(PPh3)2(PhCH2C2N2(NMe)C6H4) (4a2) as the major product. However, similar reaction with 3b selectively formed the cyclometalated complex RuCl(PPh3)2((C6H2iPr3)CH2C2N2(NMe)C6H4) (4b2). Similarly the silver(i) triazolylidenes 3a and 3b were reacted with RuHCl(H2)(PCy3)2; gave RuHCl(PCy3)2(PhCH2C2N2(NMe)Ph) (5a1), RuCl(PCy3)2(PhCH2C2N2(NMe)C6H4) (5a2) and RuCl(PCy3)2((C6H2iPr3)CH2C2N2(NMe)C6H4) (5b2), respectively. Species 3c, 3d and 3e resulted in the cyclometalated complexes (5c2, 5d2 and 5e2) as the major products as well as the ruthenium-hydride complexes (5c1, 5d1 and 5e1) as the minor products. The cyclometalated species are derived from the ruthenium-hydride complexes via C(sp2)-H activation. These Ru-complexes were shown to act as hydrogenation catalyst precursors for olefinic substrates including those containing a variety of functional groups. This journal is
Bagh, Bidraha,McKinty, Adam M.,Lough, Alan J.,Stephan, Douglas W.
p. 2712 - 2723
(2015/02/19)

POLYMERIC AND SOLID-SUPPORTED CATALYSTS, AND METHODS OF DIGESTING LIGNIN-CONTAINING MATERIALS USING SUCH CATALYSTS
Provided herein are solid base catalysts useful in non-enzymatic break down of lignin in biomass. The solid base catalysts may be polymeric catalysts or solid-support base catalysts with ionic moieties. Provided are also methods for at least partially depolymerizing lignin materials into various lignin digestion products using the solid base catalysts described herein.
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(2015/09/23)

Synthesis of polyoxymethylene dimethyl ethers from methylal and trioxane catalyzed by Br?nsted acid ionic liquids with different alkyl groups
Br?nsted acid ionic liquids with different alkyl group carbon chain lengths and an alkane sulfonic acid group were synthesized through bromoalkane, imidazole and 1,4-butane sultone as raw materials. The structures and properties of the ionic liquids were experimentally characterized. Catalytic reaction of methylal (DMM) with trioxane (TOX) for preparation of polyoxymethylene dimethyl ethers (PODMEn, CH3O(CH2O)nCH3, where n > 1) was investigated in various Br?nsted acid ionic liquids with different carbon chain length of alkyl groups. The carbon chain length of alkyl groups and activity correlation for the ionic liquids was studied. It was found that the structures of ionic liquids were consistent with the designed structure and their purities were high. They possessed high thermal stability and wide liquid range. The hydrophobicity of ionic liquids became stronger with the increase of carbon chain length. With increasing the carbon chain length of ionic liquids, the selectivity of PODME3-8 is increased at first and then decreased. Among all the ionic liquids, [C6ImBS][HSO4] shows the best catalytic performance and the selectivity of PODME3-8 is 57.85%.
Wu, Qin,Li, Weijiao,Wang, Min,Hao, Yu,Chu, Tonghua,Shang, Jiqing,Li, Hansheng,Zhao, Yun,Jiao, Qingze
p. 57968 - 57974
(2015/07/20)

Synthesis of methylal from methanol and formaldehyde catalyzed by Br?nsted acid ionic liquids with different alkyl groups
The catalytic reaction of methanol with formaldehyde for the preparation of methylal was investigated in various Br?nsted acid ionic liquids with different carbon chain length of alkyl groups. The structures, acidities, and properties of ionic liquids were experimentally characterized and theoretically analyzed. The Br?nsted acidity-viscosity-activity correlation for the ionic liquids was studied. Among all these ionic liquids, [C6ImBS][HSO4] exhibited the best catalytic performance, which was ascribed to its strong Br?nsted acidity and low viscosity. The catalytic activity of the ionic liquid was near that of concentrated sulfuric acid. The influences of ionic liquid dosage, reaction temperature and molar ratio of methanol to formaldehyde were explored using [C6ImBS]HSO4 as the catalyst. Under the optimal conditions of n(methanol):n(formaldehyde):n(ILs) = 2.5:1:0.0258, 60 °C, and 4 h, the conversion of formaldehyde can reach 63.37%. The ionic liquid [C6ImBS]HSO4 could be reused.
Sun, Jiahan,Li, Hansheng,Song, Haoran,Wu, Qin,Zhao, Yun,Jiao, Qingze
p. 87200 - 87205
(2015/11/09)

Palladium nanoparticles supported on fibrous-structured silica nanospheres (KCC-1): An efficient and selective catalyst for the transfer hydrogenation of alkenes
An efficient palladium catalyst supported on fibrous silica nanospheres (KCC-1) has been developed for the hydrogenation of alkenes and α,β-unsaturated carbonyl compounds, providing excellent yields of the corresponding products with remarkable chemoselectivity. Comparison (high-resolution TEM, chemisorption) with analogous mesoporous (MCM-41, SBA-15) silica-supported Pd nanocatalysts prepared under identical conditions, demonstrates the advantage of employing the fibrous KCC-1 morphology versus traditional supports because it ensures superior accessibility of the catalytically active cores along with excellent Pd dispersion at high metal loading. This morphology ultimately leads to higher catalytic activity for the KCC-1-supported nanoparticles. The protocol developed for hydrogenation is advantageous and environmentally benign owing to the use of HCOOH as a source of hydrogen, water as a solvent, and because of efficient catalyst recyclability and durability. The recycled catalyst has been analyzed by XPS spectroscopy and TEM showing only minor changes in the oxidation state of Pd and in the morphology after the reaction, thus confirming the robustness of the catalyst.
Qureshi, Ziyauddin S.,Sarawade, Pradip B.,Albert, Matthias,D'Elia, Valerio,Hedhili, Mohamed N.,K?hler, Klaus,Basset, Jean-Marie
p. 635 - 642
(2015/03/05)

Antimicrobial activity and SAR study of new gemini imidazolium-based chlorides
A series of 70 new 3,3′(α,ω-dioxaalkyl)bis(1- alkylimidazolium) chlorides were synthesized. They were characterized with respect to surface active properties and antimicrobial activity against the following pathogens: Staphylococcus aureus, Enterococcus faecalis, Acinetobacter baumannii, Escherichia coli, Klebsiella pneumoniae, Enterobacter cloacae, Pseudomonas aeruginosa, Candida krusei, and Candida albicans. In this article, besides description of the synthesis, we characterize a set of features of these compounds, concerning their structure (described by the length of the dioxaalkan spacer and the length of the alkyl substituent in the aromatic ring) and surface active properties (critical micelle concentration, value of surface tension at critical micelle concentration, value of surface excess, molecular area of a single particle, and free energy of adsorption of molecule). Then, we present a SAR study for Staphylococcus aureus, as one of the most widespread pathogenic strains, conducted with the help of the Dominance-based Rough Set Approach (DRSA), that involves identification of relevant features and relevant combinations of features being in strong relationship with a high antimicrobial activity of the compounds. The SAR study shows, moreover, that the antimicrobial activity is dependent on the type of substituents and their position at the chloride moiety, as well as on the surface active properties of the compounds.
Pa?kowski, ?ukasz,B?aszczyński, Jerzy,Skrzypczak, Andrzej,B?aszczak, Jan,Kozakowska, Karolina,Wróblewska, Joanna,Kozuszko, Sylwia,Gospodarek, Eugenia,Krysiński, Jerzy,S?owiński, Roman
p. 278 - 288
(2014/03/21)

NHC-silver(I) complexes as chemical nucleases; Synthesis, crystal structures, and antibacterial studies
A series of N-heterocyclic carbene (NHC) precursors, 1-methoxylethyl-3- allylimidazolium hexafluorophosphate (1), 1-ethyl-3-allylimidazolium hexafluorophosphate (2), and 1-pentyl-3-allylimidazolium hexafluorophosphate (3) were synthesized. These salts were treated with Ag2O to afford their corresponding mononuclear Ag(I)-NHC complexes, namely 1-methoxylethyl-3- allylimidazolium silver(I) hexafluorophosphate (4), 1-ethyl-3-allylimidazolium silver(I) hexafluorophosphate (5), and 1-pentyl-3-allylimidazolium silver(I) hexafluorophosphate (6), respectively. These compounds were characterized by physicochemical and spectroscopy techniques. Compounds 4 and 5 were structurally characterized by single crystal X-ray diffraction, and their stability in solution was investigated and found to be acceptable for the antibacterial studies. These new NHC precursors and their respective Ag-NHC complexes were screened for their antibacterial activities against Staphylococcus aureus (ATCC 12600) and Escherichia coli (ATCC 25922). Compounds 1-3 showed no inhibition, whereas 4-6 inhibited the growth of these bacteria. The nuclease activities of the reported compounds against plasmid DNA and RNA were assessed by gel electrophoresis, and the results indicate that complexes 5 and 6 can degrade both DNA and RNA in the absence of an oxidant.
Haque, Rosenani A.,Asekunowo, Patrick O.,Razali, Mohd. R.,Mohamad, Faisal
p. 194 - 204
(2014/06/09)

New eco-friendly 1-alkyl-3-(4-phenoxybutyl) imidazolium-based ionic liquids derivatives: A green ultrasound-assisted synthesis, characterization, antibacterial activity and POM analyses
In view of the emerging importance of the ILs as "green" materials with wide applications and our general interests in green processes, a series of a twenty five new 1-alkyl-3-(4-phenoxybutyl) imidazolium-based ionic liquids (ILs) derivatives is synthesized using a facile and green ultrasound-assisted procedure. Their structures were characterized by FT-IR, 1H-NMR, 13C-NMR, 11B, 19F, 31P, and mass spectrometry. Antimicrobial screens of some selected ILs were conducted against a panel of Gram-positive and Gram-negative bacteria. The antimicrobial activity of each compound was measured by determination of the minimal inhibitory concentration (MIC) yielding very interesting and promising results. Their antibacterial activities are reported, and, on the basis of the experimental and virtual POM screening data available, attempt is also made to elucidate the structure activity relationship.
Messali, Mouslim,Aouad, Mohamed R.,El-Sayed, Wael S.,Ali, Adeeb Al-Sheikh,Hadda, Taibi Ben,Hammouti, Belkheir
p. 11741 - 11759
(2014/11/08)

Evaluation of decomposition products of EMImCl·1.5AlCl3 during aluminium electrodeposition with different analytical methods
Ionic liquids are of great importance for electrodeposition of metals, which can't be deposited from aqueous electrolytes due to their negative standard potentials. In this paper non-woven polymers were coated with aluminium by electrodeposition from 1-et
Poetz, Sandra,Handel, Patricia,Fauler, Gisela,Fuchsbichler, Bernd,Schmuck, Martin,Koller, Stefan
p. 6685 - 6690
(2014/02/14)

Half sandwich ruthenium(ii) hydrides: Hydrogenation of terminal, internal, cyclic and functionalized olefins
Bis(1,2,3-triazolylidene) silver(i) complex 1a was reacted with [RuCl2(p-cymene)]2 to give the ruthenium complex [PhCH2N2(NMe)C2(C6H4CF3)]RuCl2(p-cymene) (2a) as major product in addition to the minor C(sp2)-H activated product [PhCH2N2(NMe)C2(C6H3CF3)]RuCl(p-cymene) (2a′). Similar ruthenium complexes 2b, 2c, 2d and 2e with general formula RuCl2(p-cymene)(NHC) (NHC = MesCH2N2(NMe)C2Ph 2b, PhCH2N2(NMe)C2Ph 2c, TripCH2N2(NMe)C2Ph 2d, IMes 2e) were also synthesized. Subsequent reaction of Me3SiOSO2CF3 with 2a and 2b resulted in cationic ruthenium species [(PhCH2N2(NMe)C2(C6H4CF3))RuCl(p-cymene)][OSO2CF3] (3a) and [(MesCH2N2(NMe)C2Ph)RuCl(p-cymene)][OSO2CF3] (3b), respectively. Complexes 3a and 3b dissolved in CD3CN to give [(PhCH2N2(NMe)C2(C6H4CF3))RuCl(CD3CN)(p-cymene)][OSO2CF3] (4a) and [(MesCH2N2(NMe)C2Ph)RuCl(CD3CN)(p-cymene)][OSO2CF3] (4b), respectively. Cationic ruthenium species 4a and 4b failed to show catalytic activity towards hydrogenation of olefins. Ruthenium(ii) complexes 2b-e with the general formula RuCl2(p-cymene)(NHC) were reacted with Et3SiH to generate a series of ruthenium(ii) hydrides 5b-e. These compounds 5b-e are effective catalysts for the hydrogenation of terminal, internal and cyclic and functionalized olefins.
Bagh, Bidraha,Stephan, Douglas W.
p. 15638 - 15645
(2015/01/08)

RUTHENIUM-BASED COMPLEX CATALYSTS
The present invention provides novel Ruthenium-based transition metal complex catalysts comprising specific ligands, their preparation and their use in hydrogenation processes. Such complex catalysts are inexpensive, thermally robust, and olefin selective.
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(2013/03/26)

Chemo-immunotherapeutic antimalarials targeting isoprenoid biosynthesis
We synthesized 30 lipophilic bisphosphonates and tested them in malaria parasite killing (targeting parasite geranylgeranyl diphosphate synthase, GGPPS) and human γδ T cell activation (targeting human farnesyl diphosphate synthase, FPPS). Similar patterns of activity were seen in inhibiting human FPPS and Plasmodium GGPPS, with short to medium chain-length species having most activity. In cells, shorter chain-length species had low activity, due to poor membrane permeability, and longer chain length species were poor enzyme inhibitors. Optimal activity was thus seen with ～C 10 side-chains, which have the best combination of enzyme inhibition and cell penetration. We also solved the crystal structure of one potent inhibitor, bound to FPPS. The results are of interest since they suggest the possibility of a combined chemo/immuno-therapeutic approach to antimalarial development in which both direct parasite killing and γδ T cell activation can be achieved with a single compound.
Zhang, Yonghui,Zhu, Wei,Liu, Yi-Liang,Wang, Hong,Wang, Ke,Li, Kai,No, Joo Hwan,Ayong, Lawrence,Gulati, Anmol,Pang, Ran,Freitas-Junior, Lucio,Morita, Craig T.,Oldfield, Eric
supporting information
p. 423 - 427
(2013/06/05)

Symmetrical 1, 3-Dialkylimidazolium Based Ionic Liquid Crystals
The synthesis and characterization for a series of symmetrical 1, 3-dialkylimidazolium salts with different chain lengths and counter anions together with their 1-alkylimidazole precursors are described. Liquid crystal (LC) properties of these salts are studied. Images under polarizing optical microscopy show focal conic texture together with homeotropic domains. A smectic A mesophase, typical for rod-like imida-zolium salts, is assigned. Studies from powder X-ray diffraction suggest a lamellar structure with non-interdigitated monolayer arrangement for the LC salts in the mesophase. In addition, a short note on the structure and property relationship for rod-like, discor fan-like, and dendritic shaped imidazolium ionic liquid crystals (ImILCs) forming smectic, columnar, and cubic phase is briefly summarized. Acomparison of minimum alkyl chain length needed for 1-alkyl-3-methyl and symmetrical 1, 3-dialkyl ImILCs to exhibit LC behavior is addressed.
Rohini, Rondla,Lee, Ching-Kuan,Lu, Jung-Tang,Lin, Ivan J.B.
p. 745 - 754
(2013/11/06)

Rhodium-cobalt bimetallic nanoparticles: A catalyst for selective hydrogenation of unsaturated carbon-carbon bonds with hydrous hydrazine
Our studies on the effect of metal compositions on the catalytic activity of the rhodium-based bimetallic nanocatalysts revealed that the nanoparticles with a 4:1 ratio of rhodium to cobalt, were more active than the rhodium monometallic nanoparticles in the selective hydrogenation of unsaturated carbon-carbon bonds with hydrous hydrazine as a hydrogen source. The nanocatalysts effected this hydrogenation process in good-to-excellent yields with high functional group tolerance, and could be reused 10 times without the loss of catalytic activity. The catalyst characterization by X-ray photoelectron spectroscopy, transmission electron microscopy and line-scanning analysis suggested that the coexistence of metallic rhodium and cobalt plays an important role in the enhancement of catalytic activity. Copyright
Lin, Jin,Chen, Jing,Su, Weiping
supporting information
p. 41 - 46
(2013/03/14)

Anisotropic ionic conductivity in fluorinated ionic liquid crystals suitable for optoelectronic applications
In this work, we report a library of thirteen fluorinated ionic liquids consisting of iodide salts of 1-alkyl-3-polyfluoroalkyl-imidazolium cations. By changing the length of the alkyl and polyfluoroalkyl pendants, we discovered that particular combinations of these result in compounds showing a mesophase. The nature and the molecular arrangement of the mesophase are characterised by polarised optical microscopy and powder X-ray diffraction analysis, among others. We demonstrate that, after the addition of I2 to generate the I-/I3- redox couple, anisotropic ionic conductivity takes place along preferential pathways in the lamellar structure of the mesophase. Notably, the addition of I2 does not suppress the mesophase temperature range, contrary to previously reported systems. Furthermore, the tendency of these materials to supercool allows the molecular arrangement in the mesophase to be retained in a solid film at ambient temperatures. Finally, we demonstrate their applicability as a quasi-solid electrolyte by preparing dye-sensitised solar cells with power conversion efficiencies comparable to the previous reports.
Abate, Antonio,Petrozza, Annamaria,Cavallo, Gabriella,Lanzani, Guglielmo,Matteucci, Francesco,Bruce, Duncan W.,Houbenov, Nikolay,Metrangolo, Pierangelo,Resnati, Giuseppe
p. 6572 - 6578
(2013/07/26)

Convenient syntheses of bulky group containing imidazolium ionic liquids
We report syntheses of bulky group containing imidazolium based ionic liquids. The bulky groups were introduced at N-1, C-2, and N-3 positions of the imidazole ring using convenient methodologies. Copyright
Kumar, Neeraj,Jain, Rahul
experimental part
p. 370 - 374
(2012/06/04)

A cis-bis-mixed-carbene ruthenium hydride complex: An olefin-selective hydrogenation catalyst
The N-heterocyclic carbene C3H2N2(CH 2CH2OMe)2 (1; IOMe) reacts with RuHCl(PPh 3)3 to give RuClH(IOMe)(PPh3)2 (2), which reacts further with SIMes to give the cis-bis-mixed-carbene complex RuClH(IOMe)(SIMes)(PPh3) (3). This species has been shown to be a highly effective hydrogenation catalyst that tolerates the presence of a wide range of functional and donor groups.
Lund, Clinton L.,Sgro, Michael J.,Cariou, Renan,Stephan, Douglas W.
scheme or table
p. 802 - 805
(2012/04/17)

Synthesis, photophysical properties, and molecular aggregation of gold(I) complexes containing carbon-donor ligands
A series of gold(I) complexes with N-heterocyclic carbene (NHC) and acetylide ligands, namely [Au(NHC1)(C≡CAr)] (NHC 1=1-(9-anthracenylmethyl)-3-(n)-butylimidazol-2-ylidene; 1b-1g), [Au(NHC2)(C≡CAr)] (NHC2=1,3-diethylimidazol-2- ylidene; 2b-2f) and [Au(C≡NAr)2]+ (C≡NAr=arylisocyanide; 3a-3f) have been synthesized. At room temperature, most of these gold(I) complexes are emissive in the solid state and in solutions with lifetimes in the nanosecond to submicrosecond regime. The emissions of complexes 1b-1g in solutions are assigned to 1π-π* excited states of the NHC ligand, while that of 2b-2f and 3a-3f are phosphorescent in nature. The intriguing solvatochromism of complex 3a was also investigated. Complexes 1b, 1d, 3a, and 3e aggregate into crystalline nanowires in freshly prepared THF/water dispersions. The X-ray crystallographic data reveal that 1b and 1d possess intermolecular π-π and C-H ... π interactions; while 3a was found to display intermolecular gold(I) ... π interactions. Copyright
Chow, Andy Lok-Fung,So, Man-Ho,Lu, Wei,Zhu, Nianyong,Che, Chi-Ming
supporting information; experimental part
p. 544 - 553
(2011/10/12)

1D coordination polymers of silver(I) and copper(II) based on bis(N-heterocyclic carbene) ligands: Synthesis and structural studies
The alkyl chain-linked diimidazolium (or dibenzimidazolium) salts, 1,1′-diethyl-4,4′-tetramethylene-diimidazolium-diiodide (L 1H2·I2) and 1,1′-diethyl-3, 3′-trimethylene-dibenzimidazolium-diiodide (L2H 2·I2), and their silver(I) and copper(II) coordination polymers, [L1AgI]n (1) and [L 2Cu2I4]n (2), have been prepared and characterized. Complex 1 is a 1D helical polymer generated by bidentated carbene ligands (L1) and Ag(I) atoms. The 1D polymer of 2 is formed by bidentated carbene ligands (L2) and coplanar quadrilateral Cu 2I2 units. 3D supramolecular frameworks in the crystal packings of 1 and 2 are formed via intermolecular weak interactions, including C-H?π contacts, π-π interactions and C-H?I hydrogen bonds.
Liu, Qing-Xiang,Shi, Meng-Chao,Wang, Zhi-Qiang,Liu, Shu-Wen,Ge, Shu-Sheng,Zang, Yan,Wang, Xiu-Guang,Guo, Jian-Hua
scheme or table
p. 2121 - 2126
(2011/01/08)

Thermal stability of ionic liquids assessed by potentiometric titration
The long-term thermal stability of imidazolium-based ionic liquids is addressed here. We have found that potentiometric titration is a precise, low-cost and quick analytical method to assess the quality changes occurring during the thermal aging of ionic liquids. Using this protocol, we have discovered that imidazolium-based ionic liquids start to decompose, to a small extent, at much lower temperatures than those inferred from thermogravimetric analysis.
Meine, Niklas,Benedito, Flavio,Rinaldi, Roberto
body text
p. 1711 - 1714
(2011/02/22)

A new stable CNHCCHCNHCN-heterocyclic dicarbene ligand: Its mono- and dinuclear Ir(i) and Ir(i)-Rh(i) complexes
The ligand [(1,3-phenylene)bis(methylene)]bis(1-ethyl-imidazol-2-ylidene) (2) (abbreviated as EtCNHCCHCNHC with CH = central aromatic ring, = CH2 spacer) has been synthesised, and isolated, by deprotonation of [(1,3-phenylene)bis(methylene)]bis(1-ethyl- imidazolium) dichloride, Et(CHimid.CHCH imid.)Cl2 (1) with LiN(SiMe3)2. This new, remarkably stable NHC dicarbene ligand is quantitatively protonated with HBr to form [(1,3-phenylene)bis(methylene)]bis(1-ethyl-imidazolium) dibromide Et(CHimid.CHCHimid.)Br2 (3) and reprotonated slowly enough in MeOH to allow observation of the monoprotonated intermediate 4. Dicarbene 2 reacts with S8 to give the dithione compound [(1,3-phenylene)bis(methylene)]bis(1-ethyl-imidazol-2-thione) Et[(SC)CH(CS)] (6). Reaction of 2 with [IrCl(CO)(PPh 3)2] and [Ir(μ-Cl)(cod)]2 yielded the mononuclear [Ir(CO)(PPh3)2Et(CH imid.CHCNHC)(PF6)](PF6) (8) and [IrCl(cod)Et(CHimid.CHCNHC)](PF6) (10) complexes, respectively, and the dinuclear complexes [{Ir(CO)(PPh 3)2}2Et(μ-CNHCCHC NHC)](PF6)2 (7) and [{IrCl(cod)} 2Et(μ-CNHCCHCNHC)] (9), respectively, in which 2 acts as a bridging, non-pincer type ligand. Only one other Ir(i) complex has been reported before containing a C NHCCHCNHC ligand. The structures of 6 and 9 were determined by X-ray diffraction and depict different conformations of the (1,3-phenylene)bis(methylene) (or xylylene) moiety. The mononuclear Ir complex 9 reacted smoothly with [Rh(μ-Cl)(cod)]2 and Cs2CO 3 to generate a rare example of a heteronuclear NHC complex, [IrRhCl2(cod)2Et(μ-CNHCCHC NHC)] (11).
Raynal, Matthieu,Cazin, Catherine S. J.,Vallee, Christophe,Olivier-Bourbigou, Helene,Braunstein, Pierre
experimental part
p. 3824 - 3832
(2009/09/26)

Reactions of allenyl- and vinylphosphonates with imidazole
Dialkyl 3-methylbuta-1,2-dienyl- and vinylphosphonates take up imidazole at the β-carbon atom in the unsaturated fragment to give the corresponding β-(1H-imidazol-1-yl)alkenyl-and alkylphosphonates.
Khusainova,Berdnikov,Mostovaya,Rybakov,Cherkasov
p. 1703 - 1705
(2008/09/18)

Synthesis and properties of chiral imidazolium ionic liquids with a (1R,2S,5R)-(-)-menthoxymethyl substituent
A series of 1-[(1R,2S,5R)-(-)-menthoxymethyl]-3-alkylimidazolium salts have been synthesized, producing both hydrophilic and hydrophobic chiral imidazolium ionic liquids. Their physicochemical properties, single-crystal X-ray structures, antimicrobial activities, and antielectrostatic effects were determined and these compounds have proven to represent not only potential new solvents in asymmetric synthesis, but also effective, disinfectants with antielectrostatic activity. Given the number and diversities of the possible conformations and interionic interactions, coupled with the chiral nature of the cations, it should come as no surprise that these salts exhibit ionic liquid behavior and are so difficult to crystallize. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.
Pernak, Juliusz,Feder-Kubis, Joanna,Cieniecka-Ros?onkiewicz, Anna,Fischmeister, Cedric,Griffin, Scott T.,Rogers, Robin D.
p. 879 - 892
(2008/02/12)

DISTILLATION OF IONIC LIQUIDS
The invention relates to a method for the distillation of ionic liquids. According to said method, in one step the pressure is set to a value below the ambient pressure and in a subsequent step, the ionic liquid is heated to a temperature ranging between 60 °C and 350 °C. The method is used in particular for purifying ionic liquids.
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Page/Page column 14-15

(2008/06/13)

Thermal degradation of ionic liquids at elevated temperatures
Ionic liquids based on the imidazolium cation are found to degrade, yielding volatile degradation products, at temperatures significantly lower than previously reported and thus a parameter Tz/x (the maximum operating temperature) is developed to provide a more appropriate estimate of thermal stability.
Baranyai, Krisztian J.,Deacon, Glen B.,MacFarlane, Douglas R.,Pringle, Jennifer M.,Scott, Janet L.
p. 145 - 147
(2007/10/03)

Pd(II) complexes of N-allyl substituted N-heterocyclic carbenes
The unsymmetrically substituted imidazolium salt 1-ethyl-3-allyl- imidazolium bromide 1 was synthesized by treatment of imidazole with one equivalent each of n-butyl lithium and ethyl bromide followed by treatment with one equivalent of allyl bromide. The symmetrically substituted derivatives 1,3-diallyl-imidazolium bromide 2 and 1,3-bis(3-methyl-2-butenyl)-imidazolium bromide 3 were obtained from imidazole and two equivalents of allyl bromide or 4-bromo-2-methyl-2-butenyl bromide, respectively, in the presence of sodium hydrogencarbonate as a base. The imidazolium bromides 1-3 react with Pd(OAc)2 to afford the palladium(II) dicarbene complexes trans-[PdBr2(L)2] (L = 1-ethyl-3-allyl-imidazolin-2- ylidene, 4; L= 1,3-diallyl-imidazolin-2-ylidene, 5; L= 1,3-di(3-methyl-2- butenyl)imidazolin-2-ylidene, 6) by in situ deprotonation of the imidazolium salts. The X-ray structure analyses of 4-6 show all three complexes to be mononuclear with palladium(II) coordinated in a square-planar fashion by two carbene and two bromo ligands.
Hahn, F. Ekkehardt,Heidrich, Beate,Lügger, Thomas,Pape, Tania
p. 1519 - 1523
(2007/10/03)

Aromatic sulfone hydroxamic acid metalloprotease inhibitor
A treatment process is disclosed that comprises administering an effective amount of an aromatic sulfone hydroxamic acid that exhibits excellent inhibitory activity of one or more matrix metalloprotease (MMP) enzymes, such as MMP-2, MMP-9 and MMP-13, while exhibiting substantially less inhibition at least of MMP-1 to a host having a condition associated with pathological matrix metalloprotease activity. Also disclosed are metalloprotease inhibitor compounds having those selective activities, processes for manufacture of such compounds and pharmaceutical compositions using an inhibitor. A contemplated compound corresponds in structure to formula B, below,
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(2008/06/13)

Synthesis of N-alkylated derivatives of imidazole as antibacterial agents
N-Alkylation of imidazole, 2-methylimidazole and 2-methyl-4-nitroimidazole have been carried out to achieve effective antibacterial agents. The products were then investigated for antibacterial activity against Escherichia coil, Staphylococcus aureus and Pseudomonas aeruginosa. Antibacterial effects of 1-alkylimidazole derivatives increase as the number of carbons in alkyl chain increases up to nine carbons. Also substitution of 2-methyl and 2-methyl-4-nitro groups on imidazole ring increases the antibacterial activity.
Khabnadideh,Rezaei,Khalafi-Nezhad,Bahrinajafi,Mohamadi,Farrokhroz
p. 2863 - 2865
(2007/10/03)

1,2,3-Benzothiadiazole derivatives
Novel 1,2,3-benzothiadiazole derivatives of the formula STR1 in which Het has the meanings set forth in the specification, and addition products thereof with an acid or metal salt are very effective for the control of undesired microorganisms. Novel intermediates of the formulae STR2 in which Het1 and R5 have the meanings given in the specification.
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(2008/06/13)

Enthalpies of combustion, heat capacities, and enthalpies of vaporization of 1-ethylimidazole and 1-ethylpyrazole
The standard (p° = 0.1 MPa) molar enthalpies of formation for liquid 1-ethylimidazole and 1-ethylpyrazole were derived from the standard molar enthalpies of combustion ΔcH°m, in oxygen, at T = 298.15 K, measured by static bomb combustion calorimetry. The molar heat capacities of both liquids were measured in the temperature range (280 to 365 ) K by differential scanning calorimetry. The standard molar enthalpies of vaporization Δg1H°m, at the temperature T = 298.15 K were measured by Calvet microcalorimetry. The derived standard molar enthalpies of formation in the gaseous state are compared. -ΔcH°m(1)/(kJ·mol-1) Δg1H°m/(kJ·mol-1) 1-Ethylimidazole 3155.7 + 4.7 66.0 + 3.9 1-Ethylpyrazole 3190.2 + 2.1 53.3 + 2.4
Ribeiro Da Silva, Manuel A. V.,Ribeiro Da Silva, Maria Das Dores M. C.,Matos, M. Agostinha R.,Jimenez, Pilar,Roux, M. Victoria,Elguero, Jose,Claramunt, Rosa,Cabildo, Pilar,Sanchez-Migallon, Ana
p. 129 - 138
(2007/10/03)

Selective N-Alkylation of Imidazole with Alcohols over Calcined Layered Double Hydroxides
Vapor-phase N-alkylation syntheses of imidazole were carried out with MeOH and EtOH over a series of calcined MgII-AlIII layered double hydroxides (LDHs) selectively produced in high yields of N-methyl (70%) and N-ethyl (63%) imidazoles only on the 3 : 1 atomic ratio of MgII-AlIII calcined LDH. Attempts on C-alkylation and dialkylation reactions over the same catalysts proved to be unsuccessful.
Santhanalakshmi, Jayadevan,Raja, Thirumalaiswamy
p. 2829 - 2831
(2007/10/03)

Regioselective N-Alkylation of Imidazoles with Alcohols over Zeolites
Vapour-phase alkylation of 4(5)-methylimidazole with MeOH over Y-zeolites selectively gave 1,5-dimethylimidazole in high yield, while the alkylation over Beta-zeolite gave 1,4-dimethylimidazole predominantly.
Ono, Yoshio,Izawa, Yuriko,Fu, Zi-hua
p. 9 - 10
(2007/10/02)

Alkylation of imidazole by solid-liquid phase transfer catalysis in the absence of solvent
Phase Transfer Catalysis in the absence of solvent is described as a useful and general method for the selective N-alkylation of imidazole. In all cases high yields are obtained while quaternization is avoided.
Diez-Barra,De La Hoz,Sanchez-Migallon,Tejeda
p. 1783 - 1786
(2007/10/02)

ELECTROREDUCTIVE N-ALKYLATION OF AMIDES, CARBAMATES, AND N-HETEROCYCLES
The N-alkylation of amides, lactams, carbamates, and N-heterocycles was easily attained in good yields by the electroreduction of the substrates in the presence of alkyl halides.
Shono, Tatsuya,Kashimura, Shigenori,Nogusa, Hideo
p. 425 - 428
(2007/10/02)

N-Alkylation of Pyrrole, Indole, and Several Other Nitrogen Heterocycles Using Potassium Hydroxide as a Base in the Presence of Polyethylene Glycols or Their Dialkyl Ethers
The alkylation of pyrrole and indole in aqueous potassium hydroxide-organic two-phase systems in the presence of polyethylene glycols (PEG) or their dialkyl ethers (PEG-ether) as phase transfer catalysts (PTC) gave substantial quantities of the C-alkylated and C,N-polyalkylated products as well as the N-alkylated products.This fact is similar to that obtained in the presence of quaternary ammonium salts as PTC.In powdered potassium hydroxide-organic two-phase system, the yields of the N-alkylated products were generally high.Especially, when PEG-ether were employed as solvents, the N-alkylated products were obtained in excellent yields under mild conditions.Imidazole, benzimidazole, carbazole, 2-methylindole, and benzotriazole were similarly N-alkylated in high yields by this method.
Sukata, Kazuaki
p. 280 - 284
(2007/10/02)

Orthoamides, XXXVIII. - Contributions to the Chemistry of Orthocarbonic Acid Esters and α,α,α-Trialkoxyacetonitriles
The reactivity of the orthocarbonates 4 and the nitriles 1 has been investigated.Carboxylic acids are esterified by 4b. Orthocarbonates 4c-f and 9b are prepared by transesterification of 4b.Mixed substituted orthocarbonates 8c-f are obtained from the nitriles 1a,b.The nitriles 2a and 3a react with alkali alcoholate in alcohol to yield the orthocarbamic acid esters 13a,b. Spirocyclic orthocarbonates 17a-d are prepared from 4b and 1,2 or 1,3-dioles, respectively. The reaction of phenol with 1b affords the mixed substituted orthocarbonate 18a. Catechol is converted by 1a into the orthocarbonate 20a.Reactions of 4b with amines and ami ne derivatives are studied. In the course of these investigations guanidines 21, imidocarbonic acid esters 22a-c, 30, carbamic acid esters 25, ureas 26, the isourea derivative 29, as well as the 1,3,4-oxadiazole 31 are prepared. The mechanism of these reactions is discussed. Imidocarbonic acid esters 22d-f, 38, N-cyanocarbamates 39, and isoureas 37 can be prepared from 1b and amines or amine derivatives. 2a as well as 13b react with cyanamide to give the N-cyanoisourea 40. Ureas 26 are formed in the reaction of 1a,b with secondary amines at elevated temperatures.The guanidinium cyanide 41a can be obtained by reaction of pyrrolidine with 1b in ether, whereas under similiar conditions from 1a and pyrrolidine the amidine 42 is produced. o-Aminophenol, o-phenylenediamine and anthranilic acid are cyclized by 4b or 1b to afford the heterocyclic compounds 43-45. α- and β-amino acids are transformed by 4b or 1b into the N-(ethoxycarbonyl)amino acid esters 46 and 47, respectively.
Kantlehner, Willi,Maier, Thomas,Loeffler, Wolfgang,Kapassakalidis, Joanis J.
p. 507 - 529
(2007/10/02)

Anodic oxidation of organophosphorus compounds. III. Anodic alkoxylation and thioalkoxylation of triphenylphosphine
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Ohmori,Nakai,Sekiguchi,Masui
p. 910 - 915
(2007/10/02)

Substituent and Solvent Effects in the Kinetics of N-Alkylimidazole-Catalyzed Reaction of Acetic Anhydride with Isopropyl Alcohol
The overall rate of the N-alkylimidazole-catalyzed reaction of acetic anhydride with isopropyl alcohol is rather insensitive to solvent polarity.Of the nine solvents studied, N,N-dimethylformamide is the best for analytical use.A series of N-alkyl substituted imidazoles was investigated as catalysts in this reaction.The most effective catalyst was N-n-pentylimidazole, which is about 60percent more reactive than N-methylimidazole.
Pandit, Nivedita K.,Obaseki, Andrew O.,Connors, Kenneth A.
p. 1678 - 1679
(2007/10/02)