Chinese Journal of Chemistry

Cover image for Chinese Journal of Chemistry

August, 2009

Volume 27, Issue 8

Pages 1449–1634

  1. Communication

    1. Top of page
    2. Communication
    3. Full Papers
    1. Formation and Structure of an Anionic Ruthenaborane Compound: [Et4N][(PPh3)2ClRuB12H12] (pages 1449–1451)

      Yong NIE, Haiyan CHEN, Jinling MIAO, Hongwei CHEN, Daqi WANG, Jianmin DOU and Guoxin SUN

      Version of Record online: 27 AUG 2009 | DOI: 10.1002/cjoc.200990243

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      Reaction of RuCl2(PPh3)3 with closo-B12H122− results in the formation of title compound, as a red air-stable species. It may be formally regarded as either a ruthenium(II) complex of closo-B12H122− via three B-H-Ru three-center two-electron bonds, or as a 13-vertex pileo2n-electron ruthenaborane cluster with a capped closo polyhedral cluster.

  2. Full Papers

    1. Top of page
    2. Communication
    3. Full Papers
    1. Investigation on the Scavenging Mechanism of 1,4-Dicarbonyls by Pyridoxamine: A Density Functional Theory Study (pages 1452–1458)

      Xin CHEN, Qingan QIAO, Zhengting CAI, Yueqing JIN, Jie JING, Xiaomin SUN, Lixiang SUN, Honglan CAI and Dacheng FENG

      Version of Record online: 27 AUG 2009 | DOI: 10.1002/cjoc.200990244

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      The scavenging mechanism for the reaction of pyridoxamine (PM) and 4-oxopentanal (OPA) was theoretically investigated by density functional theory (DFT) B3LYP at 6-31G∗ basis level together with MP2/6-31+G∗∗ single point calculation on the stationary points. The results indicated that the reaction could be achieved through two continuous steps to generate the final product, a pyrrole-type compound. Our results have verified the presumption from experiments.

    2. Xylene as a New Polymerizable Additive for Overcharge Protection of Lithium Ion Batteries (pages 1459–1463)

      Qianyu ZHANG, Chenchen QIU, Yanbao FU and Xiaohua MA

      Version of Record online: 27 AUG 2009 | DOI: 10.1002/cjoc.200990245

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      The electrochemical properties and overcharge protection mechanism of xylene as a new polymerizable electrolyte additive for overcharge protection of lithium ion batteries were studied by cyclic voltammetry tests, charge-discharge performance and battery power capacity measurements.

    3. Electrosyntheses of α -Hydroxycarboxylic Acids from Carbon Dioxide and Aromatic Ketones Using Nickel as the Cathode (pages 1464–1470)

      Gaoqing YUAN, Zhifa LI and Huanfeng JIANG

      Version of Record online: 27 AUG 2009 | DOI: 10.1002/cjoc.200990246

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      With Ni as the cathode and Al as the anode, aromatic ketones (acetophenone, benzophenone, 6-methoxy-2-acetonaphthone, 4-methylacetophenone and 4-methoxyacetophenone) could be successfully electrocarboxylated with CO2 (4 MPa) in an undivided cell containing n-Bu4NBr-DMF electrolyte at a constant current under room temperature, affording the corresponding α-hydroxycarboxylic acids in good to excellent yields (56%–90%).

    4. Synthesis and Mesophase Behaviour of Morpholinium Ionic Liquid Crystals (pages 1471–1475)

      Wei YU, Hui PENG, Haibo ZHANG and Xiaohai ZHOU

      Version of Record online: 27 AUG 2009 | DOI: 10.1002/cjoc.200990247

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      The effect of hydrogen bonds in the Mor1,16BF4 would lead to the stabilization and conformational change of mesophase.

    5. Synthesis, Crystal Structure and Magnetic Properties of a New cis-Heterotrinuclear [CuL-Mn-CuL] Complex (pages 1476–1480)

      Fuan LI, Hongling LIU, Guopeng LI and Ruojie TAO

      Version of Record online: 27 AUG 2009 | DOI: 10.1002/cjoc.200990248

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      Crystal structure and magnetic properties of a cis-heterotrinuclear complex [(CuL)2Mn(H2O)2]· CH3OH have been determined and studied.

    6. Syntheses, Structures and Luminescence Properties of Ln-Coordination Polymers Based on Flexible Thiodiacetic Acid Ligand (pages 1481–1486)

      Xiangyang HOU, Dongsheng LI, Xiao WANG, Jijiang WANG, Yixia REN and Meili ZHANG

      Version of Record online: 27 AUG 2009 | DOI: 10.1002/cjoc.200990249

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      Two novel lanthanide complexes with the formulas [Ln2(tda)3(H2O)2]n [Ln=Sm (1), Dy (2), H2tda=thiodiacetic acid] have been constructed under hydrothermal reactions. Interestingly, the two complexes are isostructural and present a 2D network with (3,4,5,6)-connected (47·68)(44·66)(45·6)(46)(43) topology. In addition, their thermogravimetric and photoluminescence properties have also been investigated.

    7. Solid State Oxidative Aromatization of Hantzsch 1,4-Dihydropyridines to Pyridines Using Iodobenzene Diacetate or Hydroxy(tosyloxy)iodobenzene (pages 1487–1491)

      Parvin KUMAR

      Version of Record online: 27 AUG 2009 | DOI: 10.1002/cjoc.200990250

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      An easy, safe, solvent-free and effective method for oxidative aromatization of Hantzsch 1,4-dihydropyridines catalyzed by hypervalent iodine (IBD and HTIB) to corresponding pyridine derivatives in high yields within short span of time. All reactions were carried out just by grinding the two reactants.

    8. Synthesis, Characterization and Properties of Amide Anions Based Ionic Liquids Containing Nitrile Group (pages 1492–1500)

      Ting ZOU, Liang LU, Xiuli LIU, Zhan ZHANG, Yunrong XUE, Yu YANG, Caimeng Li, Xianlei FU and Guohua GAO

      Version of Record online: 27 AUG 2009 | DOI: 10.1002/cjoc.200990251

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      A series of amide anion based ionic liquids containing nitrile groups have been synthesized using the method of ion-exchange between potassium amide and various quaternary halide salts of trimethylamine, triethylamine, tributylamine, N-methylpyrrolidine, and N-methylimidazole. The synthesized ionic liquids exhibited advantageously high thermal stability. The decomposition temperature ranged from 224 to 289°C. The functionalised ionic liquid, [EMIm][N(CN)COC2H5], was used as a ligand for Suzuki coupling reaction, resulting in the increase of the yields by 10% –20%.

    9. Microwave-assisted Oxidation of Alcohols and Polyarenes with Cetyltrimethylammonium Bromochromate (pages 1501–1504)

      Mohammad Kazem MOHAMMADI, Shahriare GHAMMAMY and Hossein IMANIEH

      Version of Record online: 27 AUG 2009 | DOI: 10.1002/cjoc.200990252

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    10. Fading Spectrophotometric Method for the Determination of Polyvinylpyrrolidone with Eosin Y (pages 1505–1509)

      Lihong YU, Zhongfang LIU, Shaopu LIU, Xiaoli HU and Linfeng LIU

      Version of Record online: 27 AUG 2009 | DOI: 10.1002/cjoc.200990253

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      This paper describes a sensitive, simple and rapid new method for the determination of trace amounts of PVP based on fading spectrophotometric method. In pH 2.4–3.4 weak acid medium, eosin Y was reacted with polyvinylpyrrolidone (PVP) to form a binding product, a fading reaction of EY appeared and the maximum fading wavelength was still located at 517 nm. At the same time, a smaller absorption peak was observed at 545 nm.

    11. One-pot Synthesis of 14-Aryl-1,6,7,14-tetrahydrodibenzo-[a,i]acridine-1,6-dione in Ionic Liquid (pages 1510–1514)

      Yuling LI, Xiaoping XU, Daqing SHI and Shunjun JI

      Version of Record online: 27 AUG 2009 | DOI: 10.1002/cjoc.200990254

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      A series of 14-aryl-1,6,7,14-tetrahydrodibenzo[a,i]acridine-1,6-diones have been synthesized by three-component reactions of aromatic aldehyde, 2-hydroxy-1,4-naphthoquinone and naphthalen-2-amine in ionic liquid [bmim]BF4 at room temperature. Particularly valuable features of this method include high yields of products, recyclable reaction media, broad substrate scope, short reaction time and operational simplicity.

    12. Pyridinium Conjugated Ferrocenes with Thien and Bithien Bridges: Synthesis and Electrochemical Properties (pages 1515–1522)

      Yonghua GONG, Wenwei QIU, Fan YANG, Pierre AUDEBERT, Gilles CLAVIER, Fabien MIOMANDRE and Jie TANG

      Version of Record online: 27 AUG 2009 | DOI: 10.1002/cjoc.200990255

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      Three di- and tri-branched pyridinium salts with ferrocene ends and thienyl or bithienyl bridges were designed and successfully synthesized. The electrochemical properties of these compounds were primarily investigated.

    13. Manganese Dioxide Mediated Stereoselective, One-step Synthesis of Novel Steroidal (6R)-Spiro-1',2′,4′-triazoline-3′-thiones (pages 1523–1525)

      SHAMSUZZAMAN, Nazish SIDDIQUI, Anwar SALIM and M. K. AKRAM

      Version of Record online: 27 AUG 2009 | DOI: 10.1002/cjoc.200990256

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      Oxidative cyclization of 5α-cholestan-6-one thiosemicarbazone (1), its 3β-chloro (2) and 3β-acetoxy (3) analogues with active manganese dioxide at room temperature afforded selectively the corresponding (6R)-spiro-1',2′,4′-triazoline-3′-thiones 46. This synthesis has the advantages of mild reaction conditions, easy handling, easily available reagent and high yields.

    14. Colorimetric Sensors for Anion Recognition Based on the Proton Transfer Signaling Mechanism (pages 1526–1530)

      Xiaohuan HUANG, Yongbing HE, Zhihong CHEN and Chenguang HU

      Version of Record online: 27 AUG 2009 | DOI: 10.1002/cjoc.200990257

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      Phenolic hydroxyl based sensors 1, 2 and 3 can act as selective colorimetric sensors. The most pronounced effect is the F-induced color change, which is clearly visible to the naked eyes.

    15. Synthesis of Novel Bis-spiroisoxazolines through 1,3-Dipolar Cycloaddition of Nitrile Oxide with α,α'-Bis(arylmethylidene)cycloalkanone (pages 1531–1536)

      Xiaofang LI, Xianyong YU and Yaqing FENG

      Version of Record online: 27 AUG 2009 | DOI: 10.1002/cjoc.200990258

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      A new class of bis-spiroisoxazolines was prepared in moderate to good yields in a highly regioselective cycloaddition of nitrile oxide with bis(arylmethylidene)cycloalkanone. The structures of the products were characterized thoroughly. The 1,3-dipolar cycloaddition has high regioselectivity and the density functional calculations provide a reasonable explanation on the reaction.

    16. Cross-aldol Condensation of Cycloalkanones and Aromatic Aldehydes in the Presence of Nanoporous Silica-based Sulfonic Acid (SiO2-Pr-SO3H) under Solvent Free Conditions (pages 1537–1542)

      Ghodsi MOHAMMADI ZIARANI, Alireza BADIEI, Alireza ABBASI and Zahra FARAHANI

      Version of Record online: 27 AUG 2009 | DOI: 10.1002/cjoc.200990259

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      The aromatic aldehydes underwent cross aldol condensation with cycloalkanones in the presence of a catalytic amount of nanoporous silica-based sulfonic acid (SiO2-Pr-SO3H) under solvent-free conditions to afford the corresponding α,α′-bis(substituted benzylidene)cycloalkanones in excellent yields with short reaction time without any side reactions. This method is very general, simple and environmentally friendly in contrast with other existing methods. SiO2-Pr-SO3H was proved to be an efficient heterogeneous solid acid catalyst, which could be easily handled and removed from the reaction mixture by simple filtration, and also recovered and reused without loss of reactivity.

    17. An Oligonucleotide-based Fluorescence Sensor for Mercury(II) in Aqueous Solutions (pages 1543–1547)

      Huiwang WU, Xueping LIU, Jianhui JIANG, Guoli SHEN and Ruqin YU

      Version of Record online: 27 AUG 2009 | DOI: 10.1002/cjoc.200990260

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      This Mercury(II) sensor was composed of two DNA probes functionalized with a fluorophore (fluorescein, F) and a quencher (tetramethyl rhodamine, Q) moiety separately. This pair of DNA probes contains two pairs of thymine-thymine mismatches used to detect Hg(II) ions. In the presence of Hg(II) ions, thymine-Hg2+-thymine was formed between thymine residues of probes. From that, the interaction of the two DNA probes increased. Thus, the DNA probes formed double-stranded structure. Both fluorophore and quencher were brought close to each other leading to the fluorescence resonance energy transfer (FRET) between F and Q. The decrease of the fluorescence intensity was related to the concentration of Hg(II) ions.

    18. 1-Butyl-3-methylimidazolium Hydrogen Sulfate [bmim]HSO4: An Efficient Reusable Acidic Ionic Liquid for the Formylation of Alcohols (pages 1548–1552)

      Khodabakhsh NIKNAM, Mohammad Ali ZOLFIGOL, Dariush SABERI and Mahdi KHONBAZI

      Version of Record online: 27 AUG 2009 | DOI: 10.1002/cjoc.200990261

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      1-Butyl-3-methylimidazolium hydrogen sulfate [bmim]HSO4 as an acidic ionic liquid was prepared and used as a catalyst for the formylation of alcohols with ethyl formate at room temperature with good to excellent yields. A good selectivity was observed for the formylation of primary alcohols in the presence of tertiary alcohols.

    19. Aftertreatment of Conventional Direct Dyeings of Cotton with a Bis-reactive Cationic Fixing Agent (pages 1553–1557)

      Saima SHARIF, Ahmad SAEED, Naeem Khan MUHAMMAD and Fauz-ul-Azeem MUHAMMAD

      Version of Record online: 27 AUG 2009 | DOI: 10.1002/cjoc.200990262

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      A bis-reactive cationic fixing agent, ethylenebis[N-(2,3-epoxypropyl)-N,N-dimethylammonium chloride] (I) has been used as an aftertreatment reagent to improve the wash fastness of direct dyes on cotton. The effects of different pH conditions and concentrations on the effectiveness of this cationic fixing agent have been investigated. The results showed that aftertreatment at pH 11 produced dyeings with higher colour strength and better wash fastness than that at pH 7. In addition, the cationic agent at a low concentration was found to be more effective under both neutral and alkaline conditions.

    20. Ring-opening of N-Tosyl Aziridines with Hydroxyl Compounds Catalyzed by Acidic Ionic Liquid (pages 1558–1562)

      Yuling LI, Dagong GU, Xiaoping XU and Shunjun JI

      Version of Record online: 27 AUG 2009 | DOI: 10.1002/cjoc.200990263

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      Ring-opening of two types of N-tosyl aziridines with hydroxyl compounds has been studied. The aziridines could react smoothly with alcohols in the presence of functional ionic liquid [hmim]HSO4 to afford the corresponding β-amino ethers in moderate to good yields with high regioselectivity. The recyclable property of [hmim]HSO4 was demonstrated in the process.

    21. A Green and Efficient Synthesis of 13-Aryl-5,7,12,14-tetrahydrodibenzo[b,i]xanthene-5,7,12,14(13H)-tetraone Derivatives in Ionic Liquid (pages 1563–1568)

      Yuling LI, Baixiang DU, Xiaoping XU, Daqing SHI and Shunjun JI

      Version of Record online: 27 AUG 2009 | DOI: 10.1002/cjoc.200990264

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      A series of 13-aryl-5,7,12,14-tetrahydrodibenzo[b,i]xanthene-5,7,12,14(13H)-tetraones derivatives were synthesized in high yields by the reactions of aromatic aldehyde with 2-hydroxy-1,4-naphthoquinone in ionic liquid [bmim+][ BF4] at 90°C. The reaction work-up is simple and the ionic liquid can be easily separated from the product and reused.

    22. An Unexpected Green and Facile Synthesis of 2,6-Diaryl-4-styrylpyridines via Multi-component Reactions in Microwave-assisted Solvent-free Conditions (pages 1569–1574)

      Feng SHI, Ge ZHANG, Dianxiang ZHOU, Ning MA, Yajie ZHANG, Rongshun CHEN and Shujiang TU

      Version of Record online: 27 AUG 2009 | DOI: 10.1002/cjoc.200990265

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      An unexpected green and facile synthesis of 2,6-diaryl-4-styrylpyridines was realized via microwave-assisted multi-component reaction of 3-arylacrylaldehyde oxime, 1-arylethanone and ammonium acetate in solvent-free condition.

    23. Synthesis and Characterization of α-Bromo Chalcone Derivatives (pages 1575–1581)

      Yakup BUDAK and Mustafa CEYLAN

      Version of Record online: 27 AUG 2009 | DOI: 10.1002/cjoc.200990266

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      α-Bromo chalcones containing 2-thiene ring were prepared in good yields by the condensation of 1-(thien-3-yl)ethanone with aromatic aldehydes, followed by bromination with bromine and selective dehydrobromination with triethyl amine at room temperature.

    24. Synthesis of Thermostable Azo-type Photoswitches towards Photoregulating Nucleic Acid Structures (pages 1582–1588)

      Qi WANG, Shuang GAO, Kai ZHOU, Wenbin CHEN, Congwei NIU and Zhen XI

      Version of Record online: 27 AUG 2009 | DOI: 10.1002/cjoc.200990267

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      Photochemical properties of different azo-type compounds were elucidated. Based on the finding, an azobenzene linker designed as a thermostable photoswitch was incorporated into a DNA backbone to reversibly photoregulate DNA structure.

    25. Highly Efficient and Versatile Synthesis of Some Important Precursors from 1,6-Anhydrous-β-D-glucopyranose as a Green Starting Material (pages 1589–1592)

      Guohua WEI, Chao CAI and Yuguo DU

      Version of Record online: 27 AUG 2009 | DOI: 10.1002/cjoc.200990268

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      Some important precursors for complex oligosaccharide synthesis were readily prepared from a green starting material 1,6-anhydrous-β-D-glucopyranose in one or two steps with moderate to high yields. These improved methods established herein will greatly facilitate the assembly of some complex oligosaccharides for the biological study.

    26. Synthesis of a Number of 3-Alkyl Substituted Pyrrole Monomers (pages 1593–1599)

      Xuediao CAI, Evelin JAEHNE and Hans-Juergen ADLER

      Version of Record online: 27 AUG 2009 | DOI: 10.1002/cjoc.200990269

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      1-Phenylsulfonyl pyrrole was utilized as precursor in the synthesis of 3-substituted pyrroles via Friedel-Crafts acylation reaction. Subsequently, two methods were used to synthesize ω-(pyrrol-3-yl)alkylphosphonic acid esters. One starts from the brominated oxoalkyl derivatives by removing of the protecting group followed by reduction yielding ω-(pyrrol-3-yl)alkylphosphonic acid esters. Another is the reduction of carbonyl group followed by de-protection.

    27. Electrical Properties of Polypyrrole Ultra Thin Films (pages 1600–1604)

      Xuediao CAI, Evelin JAEHNE, Hans-Juergen ADLER, Wenge GUO and Geng WANG

      Version of Record online: 27 AUG 2009 | DOI: 10.1002/cjoc.200990270

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      The polypyrrole film was chemically deposited on ω-(pyrrol-1-yl alkyl)dimethylchloro- silanes modified substrates. The morphology of this polypyrrole film was investigated by SEM and AFM. The electric properties of polypyrrole films were investigated by current-potential characterization.

    28. An Unexpected and Efficient Synthesis of Open-chain Derivatives of Bistetronic Acid under Microwave Irradiation (pages 1605–1610)

      Feng SHI, Ning MA, Dianxiang ZHOU, Ge ZHANG, Bo JIANG and Shujiang TU

      Version of Record online: 27 AUG 2009 | DOI: 10.1002/cjoc.200990271

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      An unexpected and efficient synthesis of novel open-chain derivatives of bistetronic acid has been successfully achieved in glyclol under MW. This method has the prominent advantages of short reaction time, high yield, operational simplicity as well as environmental friendliness.

    29. Synthesis and Properties of Poly(vinyl alcohol)/Synthetic F-montmorillonite Nanocomposites (pages 1611–1616)

      Junhao ZHANG, Xiaofang CHENG, He LIU and Weiliang LU

      Version of Record online: 27 AUG 2009 | DOI: 10.1002/cjoc.200990272

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      Poly(vinyl alcohol) (PVA)/F-MMT nanocomposites were prepared using the synthetic F-MMT by a solution-intercalation method. Exfoliated PVA/F-MMT nanocomposites were obtained, and characterized by XRD and TEM. The results of thermal and mechanical properties indicate that thermal stability and mechanical properties of PVA nanocomposites are enhanced compared with those of pure PVA.

    30. Anion Recognition Using Novel and Colorimetric Tweezer Receptors: 1,3-Phenylenedi(carbonylhydrazone) in Aqueous-organic Binary Solvents (pages 1617–1623)

      Youming ZHANG, Aixia WANG, Cheng CAO, Yanli LENG and Taibao WEI

      Version of Record online: 27 AUG 2009 | DOI: 10.1002/cjoc.200990273

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      Anion recognition of 1,3-benzyldiacylhydrazone derivatives 3a for anions (F, Cl, Br, I, AcO, HSO4, H2PO4, ClO4) were investigated by UV-vis spectroscopy in 85% DMSO-15% H2O binary solutions, color changes from colorless to yellow were observed by the ′naked-eye′ upon the addition of AcO, F and H2PO4. 1H NMR signals indicated that the receptor 3a occur deprotonation after the addition of an excess of fluoride anion.

    31. Spectrophotometric Determination of Cimetidine through Charge-transfer Reaction with 1,5-Dichloroanthraquinone as a π-Electron Acceptor (pages 1624–1628)

      Xiaoling WEI, Liangwei DU, Lisheng WANG, Chunliu WEI and Zhiliang JIANG

      Version of Record online: 27 AUG 2009 | DOI: 10.1002/cjoc.200990274

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      This article describes a spectrophotometric determination method for cimetidine through n-π charge-transfer reaction between 1,5-dichloroanthraquinone and cimetidine, which can produce charge-transfer complex with the mole ratio of 1:2. The complex shows an obviously increasing absorption at the wavelength of 343 nm and the increasing intensity of absorbance is in direct ratio with cimetidine concentration. The method has been successfully applied to determine cimetidine tablets and capsules with a convenient manipulating procedure, a cheap detecting instrumentation, simple and low-cost measurement, an obvious, accurate and satisfied result.

    32. Synthesis and Antimicrobial Activity of Some 3-Substituted-5,6-dimethoxy-2,3-dihydrobenzo[d]thiazol-2-one (pages 1629–1634)

      Wageeh Salih El-HAMOULY, Kamelia Mahmoud AMINE, Eman Moustafa Hasan ABBAS and Eman Ali ABDEL-MAGUID

      Version of Record online: 27 AUG 2009 | DOI: 10.1002/cjoc.200990275

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      Sixteen new compounds derived from the 2,3-dihydrobenzo[d]thiazol-2-one template with various side-chains in position-3 were synthesized and evaluated for their antimicrobial activity. Antibacterial and antifungal screening of the compounds prepared showed that 5,6-dimethoxy-3-(2-oxo-propyl)-2,3-dihydrobenzo[d]thiazol-2-one (3g) exhibited the highest activity.

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