Chinese Journal of Chemistry

Cover image for Vol. 30 Issue 10

October, 2012

Volume 30, Issue 10

Pages 2257–2598

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Communications
    5. Communication
    6. Full Papers
    7. Note
    8. Erratum
    1. You have free access to this content
      Cover Picture: Sugar-fiber Imprinting to Generate Microgrooves on Polymeric Film Surfaces for Contact Guidance of Cells (Chin. J. Chem. 10/2012) (page 2257)

      Zehua Qu and Jiandong Ding

      Article first published online: 23 OCT 2012 | DOI: 10.1002/cjoc.201290026

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      The cover picture shows a facile and biocompatible approach to generate microgrooves on water-insoluble polymeric surfaces using sugar fibers as the imprinting template. The cover shows a "cotton candy", a favorite food for many children. This time, a research group in Fudan University employed it to serve science, using the sugar fibers in this "cotton" as a sacrificed template to physically modify a biomaterial. The present report is aimed to confirm the feasibility of this idea in the cases of two dimensional films, using poly(lactic-co-glycolic acid) (PLGA) as the model biomaterial matrix. Microgrooves were conveniently generated on PLGA films after removing sugar fibers simply by water. The contact guidance of cells by the microgrooves was confirmed on the resulting surface. More details are discussed in the article by Qu and Ding on page 2292–2296.

  2. Contents

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Communications
    5. Communication
    6. Full Papers
    7. Note
    8. Erratum
    1. Contents: Chin. J. Chem. 10/2012 (pages 2259–2272)

      Article first published online: 23 OCT 2012 | DOI: 10.1002/cjoc.201290027

  3. Communications

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Communications
    5. Communication
    6. Full Papers
    7. Note
    8. Erratum
    1. Accelerated Curing Speed of Ethyl α-Cyanoacrylate by Polymer with Catecholamine Groups (pages 2275–2280)

      Feng Zhang, Siwei Liu, Yi Zhang, Jiarui Xu and Yen Wei

      Article first published online: 27 SEP 2012 | DOI: 10.1002/cjoc.201200507

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      When both catecholamine and double bond are tethered to a polymer backbone simultaneously, the polymer can accelerate the curing speed of ethyl α-cyanoacrylate. Probably this is due to the catecholamine groups, which can produce free radicals and enrich them, causing free radical polymerization.

    2. Thiol-yne Click Adamantane Monolithic Stationary Phase for Capillary Electrochromatography (pages 2281–2284)

      Thi Thu Hien Dao, Mohamed Guerrouache and Benjamin Carbonnier

      Article first published online: 23 OCT 2012 | DOI: 10.1002/cjoc.201200578

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      Thiol-yne click chemistry is presented as an original approach to design adamantane-decorated porous monolith for reversed phase capillary electrochromatography.

  4. Communication

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Communications
    5. Communication
    6. Full Papers
    7. Note
    8. Erratum
    1. Iron(III)-Catalyzed Direct N-Alkylation of Azoles via Oxidative Transformation of sp3 C[BOND]H Bonds under Solvent-Free Conditions (pages 2285–2291)

      Xiang Liu, Yongxin Chen, Kangning Li, Dong Wang and Baohua Chen

      Article first published online: 23 OCT 2012 | DOI: 10.1002/cjoc.201200690

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      A new approach to synthesize N-alkylation of azoles by iron (III)-catalyst under solvent-free conditions was developed. The method is broad in scope and highly efficient.

  5. Full Papers

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Communications
    5. Communication
    6. Full Papers
    7. Note
    8. Erratum
    1. Sugar-fiber Imprinting to Generate Microgrooves on Polymeric Film Surfaces for Contact Guidance of Cells (pages 2292–2296)

      Zehua Qu and Jiandong Ding

      Article first published online: 23 OCT 2012 | DOI: 10.1002/cjoc.201200841

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      A facile and biocompatible approach to generate microgrooves on water-insoluble polymeric surfaces using sugar fibers as the imprinting template was describled.

    2. Studies toward the Synthesis of (R)-(+)-Harmicine (pages 2297–2302)

      Fanyang Mo, Fei Li, Di Qiu, Yan Zhang and Jianbo Wang

      Article first published online: 23 OCT 2012 | DOI: 10.1002/cjoc.201200672

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    3. Synthesis and Application of a Full Water-Soluble and Red-Emitting Chemosensor Based on Phenoxazinium for Copper(II) Ions (pages 2303–2308)

      Baolong Yan, Ru Sun, Jianfeng Ge, Yujie Xu, Qianqian Zhang, Xuebo Yang and Jianmei Lu

      Article first published online: 27 SEP 2012 | DOI: 10.1002/cjoc.201200452

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      A phenoxazinium-based chemosensor (1) bearing di(2-picolyl)amine unit was successfully synthesized. The result shows it is a red-emitting and full water-soluble chemosensor for the selective detection of Cu2+ in pure water. The fluorescence on-off mechanism was studied by ab initio calculations. It was also indicated that 1 had good membrane permeability and could be useful for the fluorescence microscopic imaging.

    4. Highly Efficient Synthesis of Unsymmetrical 3,3′-Bis(1H-indol-3-yl)methanes in Water (pages 2309–2314)

      Hua Lin, Yang Zang, Xingwen Sun and Guoqiang Lin

      Article first published online: 14 AUG 2012 | DOI: 10.1002/cjoc.201200496

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      A simple and practical approach for the preparation of unsymmetric bis(indolyl)-methanes (BIMs) was realized by Lewis acid InBr3-catalyzed Friedel-Crafts reaction of indoles with 3-indolyl-substituted phthalides in water.

    5. Molecular Design of D-π-A Type II Organic Sensitizers for Dye Sensitized Solar Cells (pages 2315–2321)

      Shifeng Li, Xichuan Yang, Dingfeng Qu, Weihan Wang, Yu Wang and Licheng Sun

      Article first published online: 23 OCT 2012 | DOI: 10.1002/cjoc.201200758

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    6. Palladium-Catalyzed N-Alkylation of Amides and Amines with Alcohols Employing the Aerobic Relay Race Methodology (pages 2322–2332)

      Xiaochun Yu, Lan Jiang, Qiang Li, Yuanyuan Xie and Qing Xu

      Article first published online: 14 AUG 2012 | DOI: 10.1002/cjoc.201200462

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      By employing the aerobic relay race methodology with Pd-catalyzed aerobic alcohol oxidation being a more effective protocol for alcohol activation, ligand-free homogeneous palladiums are successfully used as active catalysts in the dehydrative N-alkylation reactions of amines and amides with alcohols, giving high yields and selectivities of the alkylated amines and amides. Mechanistic studies implied that the reaction most probably proceeds via the novel relay race mechanism we recently discovered and proposed.

    7. Cinchona Alkaloid-catalyzed Asymmetric Direct Mannich Reaction of Malononitrile to Imine for Synthesis of β-Amino Malononitrile (pages 2333–2337)

      Zhijin Lu, Chen Xie, Wei Zhou, Zhiqiang Duan, Jianlin Han and Yi Pan

      Article first published online: 23 OCT 2012 | DOI: 10.1002/cjoc.201200586

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      The first direct asymmetric Mannich reaction of malononitrile to imines has been developed with cinchona alkaloid as catalyst, which provides an easy access to β-amino malononitrile with high chemical yields and excellent enantioselectivities.

    8. Preparation of Covalently-colored Polymer Latex via Batch Emulsion Polymerization (pages 2338–2342)

      Botian Li, Jie Shen, Wenjiao Ji, Guanzhi Cheng and Chengyou Kan

      Article first published online: 23 OCT 2012 | DOI: 10.1002/cjoc.201200541

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      Covalently-colored polymer latex was obtained by batch emulsion copolymerization with a red polymerizable dye. Results showed that the chromophores were mostly covalently bonded to polymer chain with consistent color brilliance and unchanged UV-Vis spectrum, and the light fastness of the resulting latex film was greatly improved.

    9. Density Functional Theory Investigation on the Second-Order Nonlinear Optical Properties of Chlorobenzyl-o-Carborane Derivatives (pages 2349–2355)

      Yan Liu, Guochun Yang, Shiling Sun and Zhongmin Su

      Article first published online: 23 OCT 2012 | DOI: 10.1002/cjoc.201200514

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      The first hyperpolarizability of the studied compounds can be substantially increased by structural modification, especially the introduction of tetrathiafulvalene.

    10. A General and Efficient CuBr2-Catalyzed N-Arylation of Secondary Acyclic Amides (pages 2356–2362)

      Mangang Wang, Hua Yu, Xinwen You, Jun Wu and Zhicai Shang

      Article first published online: 23 OCT 2012 | DOI: 10.1002/cjoc.201200701

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      A general and efficient Cu(II)-catalyzed cross-coupling method is reported for the preparation of acyclic tertiary amides. Generally moderate to excellent yields and functional group tolerance were obtained with secondary acyclic amides and aryl halides as substrates in toluene.

    11. An Efficient α-Alkylation of Aromatic Ketones with Primary Alcohols Catalyzed by [Cp∗IrCl2]2 without Solvent (pages 2363–2366)

      Jian Li, Weixing Zhang, Feng Wang, Min Jiang, Xiaochun Dong and Weili Zhao

      Article first published online: 14 AUG 2012 | DOI: 10.1002/cjoc.201200524

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    12. Theoretical Investigation on the Electron and Energy Transfer between Peripheral Carrier Transport Groups and Central Chromophores in Electroluminescent Materials (pages 2367–2375)

      Yuyu Pan, Dandan Liu, Hai Xu, Xiaodong Liu, Guannan Sun, Bing Yang and Yuguang Ma

      Article first published online: 23 OCT 2012 | DOI: 10.1002/cjoc.201200647

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      The molecular materials with structure of luminescent core and peripheral carrier groups (e.g. carbazoles), have exhibited high-performance in organic light-emitting diodes (OLEDs). There are two possible processes for the following charge bound pair generation (exciton formation): one is based on the cation of TCBzC with a positive charge on carbazole (Process 1), the other is from the anion of TCBzC with a negative charge on the central chromophore core (Process 2). These two situations lead to two kinds of exciton formations respectively (carbazole and central chromophore). Process 1 is the main factor to dominate EL, and energy-transfer process from carbazole exciton to central chromophore cores contributes to highly efficient EL.

    13. Comparison of Hair Fatty Alcohols by N-Alkylpyridinium Isotope Quaternization and Matrix-assisted Laser Desorption/ionization Mass Spectrometry for Drug Abuse Monitoring (pages 2376–2382)

      Hang Wang, Haoyang Wang, Li Zhang, Jing Zhang, Xianyi Zhuo, Yi Huang and Yinlong Guo

      Article first published online: 23 OCT 2012 | DOI: 10.1002/cjoc.201200547

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      N-Alkylpyridinium isotope quaternization (NAPIQ) method was used for comparison of fatty alcohols between normal and drug abuse group. The attached N-cationic pyridinium significantly improved the detection sensitivity for these fatty alcohols in matrix-assisted laser desorption/ionization Fourier transform ion cyclotron resonance mass spectrometric (MALDI-FTMS) analysis. The levels of fatty alcohols in the hair of heroin abuse group decreased significantly compared with the normal groups, which may be the results of the inducing of peroxidation enzyme. NAPIQ was proven to be an effective method in the research of fatty alcoholic metabolism for drug abuse monitoring without the use of isotopically coded internal standards.

    14. Gas-phase Smiles Rearrangement of Sulfonylurea Herbicides in Electrospray Ionization Mass Spectrometry (pages 2383–2388)

      Jia Zhang, Yunfeng Chai, Wei Wang, Wei Shang and Yuanjiang Pan

      Article first published online: 23 OCT 2012 | DOI: 10.1002/cjoc.201200610

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      Two competitive gas-phase Smiles rearrangements initiated by nitrogen anion and oxygen anion respectively were observed in the CID fragmentation of deprotonated rimsulfuron.

    15. Direct N-Arylation of Azaheterocycles with Aryl Halides under Ligand-free Condition (pages 2389–2393)

      Qichao Yang, Yufang Wang, Baoji Zhang and Mingjie Zhang

      Article first published online: 27 SEP 2012 | DOI: 10.1002/cjoc.201100715

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      An efficient, convenient and applicable method was developed for the N-arylation of azaheterocycles catalyzed by CuI and NaH under ligand free condition.

    16. Highly Efficient C[BOND]N Bond Forming Reactions in Water Catalyzed by Copper(I) Iodide with Calix[4]arene Supported Amino Acid Ionic Liquid (pages 2394–2400)

      Li Huang, Can Jin and Weike Su

      Article first published online: 23 OCT 2012 | DOI: 10.1002/cjoc.201200623

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      A novel and effective protocol has been developed for the Ullmann-type C[BOND]N coupling reaction catalyzed by calix[4]arene supported amino acid ionic liquid and copper(I) iodide in water under microwave irradiation condition. The protocol uses calix[4]arene supported amino acid ionic liquid as double function of the ligand and phase-transfer catalyst, and shows good tolerance in good to excellent yields.

    17. Effect of End-capping Functional Groups on the Optoelectronic Properties of Oligothiophene Derivatives (pages 2401–2410)

      Zhenyu Zuo, HongjianPP Sun and Xiaoyan Li

      Article first published online: 23 OCT 2012 | DOI: 10.1002/cjoc.201200487

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      The five novel oligothiophene derivatives (MSO2RP3T, MSP3T, EtOP3T, AcP3T and BP3T) with different functional groups were synthesized. The effect of end-capping groups on optoelectronic properties of the oligothiophene derivatives was explored. This paper provides useful information for design of tailored molecule through searching the relationships between functional groups and optoelectronic properties.

    18. Synthesis of 2(5H)-Furanone Derivatives with Bis-1,2,3-triazole Structure (pages 2411–2422)

      Jingpei Huo, Meixiang LÜ, Zhaoyang Wang and Yizhong Li

      Article first published online: 23 OCT 2012 | DOI: 10.1002/cjoc.201200638

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      A series of new chiral 2(5H)-furanone derivatives containing bis-1,2,3-triazole moiety are designed and synthesized from 4 basic unit molecules under mild conditions via the sequential three steps, including asymmetric Michael addition-elimination, substitution and no-ligand click reaction.

    19. Design, Synthesis and Antiproliferative Activities of Diaryl Thiourea Derivatives as Anticancer Agents (pages 2423–2430)

      Jianwen Yao, Zuopeng He, Jing Chen, Daquan Chen, Wei Sun and Wenfang Xu

      Article first published online: 23 OCT 2012 | DOI: 10.1002/cjoc.201200708

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      Two series of diaryl thiourea derivatives have been designed, prepared, and tested for cytotoxicity against human tumor cells PC-3, HCT116 and MDA-MB-231. The results showed that all compounds generally had antiproliferative activity against PC-3 cells, and some compounds demonstrated competitive antiproliferative activities to sorafenib.

    20. Structural, Electronic and Optical Properties of Multifunctional Iridium(III) and Platinum(II) Metallophosphors for Organic Light-Emitting Diodes (pages 2431–2439)

      Xueqin Ran, Jikang Feng, Waiyeung Wong, Aimin Ren, Guijiang Zhou and Chiachung Sun

      Article first published online: 23 OCT 2012 | DOI: 10.1002/cjoc.201200273

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      Obvious metal-to-ligand charge transfer (MLCT) occurs during low energy transitions, which is the decisive factor for the occurrence of spin-forbidden electron transition. The introduction of triphenylamino (TPA) units improves hole-creation ability and the extent of conjugation, leading to red-shifts in absorption and emission spectra.

    21. Synthesis of CdTe Quantum Dots with Tunable Photoluminescence Using Tellurium Dioxide as Tellurium Source (pages 2440–2444)

      Shengyan Liu, Yilin Wang, Kun Yang and Liya Zhou

      Article first published online: 23 OCT 2012 | DOI: 10.1002/cjoc.201200601

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      A simple and convenient method has been developed for synthesis of water-soluble CdTe quantum dots (QDs) under ambient atmospheric conditions. In contrast to the traditional aqueous synthesis, green to red emitting CdTe QDs were prepared by using TeO2 to replace Te or Al2Te3 as tellurium source in this method. With reflux time increasing from 5 to 180 min, the photoluminescence (PL) spectrum of CdTe QDs shifts from 533 to 612 nm.

    22. Synthesis and Properties of Degradable Copolymers Composed of Poly(ε-caprolactone) and 3,4-Dihydroxycinnamic Acid (pages 2445–2452)

      Jihang Li, Dongjian Shi, Huaqing Xu, Na Hu, Weifu Dong and Mingqing Chen

      Article first published online: 23 OCT 2012 | DOI: 10.1002/cjoc.201200457

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      Photoreactive and degradable hyperbranched copolymers PCL-co-PDHCA have been synthesized, and the properties have been also discussed.

    23. Slightly Cross-Linked Polyrotaxanes Made by Linking α-Cyclodextrins Entrapped in Polyrotaxanes Using Hexamethylene Diisocyanate (pages 2453–2460)

      Shuo Li, Jin Wang, Lan Jiang, Lin Ye, Aiying Zhang and Zengguo Feng

      Article first published online: 27 SEP 2012 | DOI: 10.1002/cjoc.201200280

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      Polyrotaxane-based triblock copolymers were first synthesized via the ATRP of NIPAAm initiated with the self-assembly of a distal 2-bromoisobutyryl end-capped Pluronic 17R4 with a varying amount of α-CDs in the presence of CuCl/PMDETA at 25°C in aqueous solution. Those α-CDs entrapped on the polymer chain were then linked with hexamethylene diisocyanate to give rise to novel slightly cross-linked polyrotaxanes in DMF at 45°C.

    24. A Convenient Hydrogenation Method for the Synthesis of Metallo-mesoporphyrin IX Dimethyl Esters via Self-catalyzed CoCl2-NaBH4 Reagent System (pages 2461–2465)

      Shichao Xu, Bingcheng Hu, Tianjing Hu, Huan Wang, Xiuyou Huang, Xingkun Lou and Zuliang Liu

      Article first published online: 23 OCT 2012 | DOI: 10.1002/cjoc.201200581

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    25. Synthesis and Properties of New Fluorinated Polyimides Derived from an Unsymmetrical and Noncoplanar Diamine (pages 2466–2472)

      Chenyi Wang, Xiaoyan Zhao and Guang Li

      Article first published online: 14 AUG 2012 | DOI: 10.1002/cjoc.201200431

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      A new unsymmetrical and noncoplanar aromatic diamine monomer has been successfully synthesized in high yield by a facile reaction route. New series of highly soluble fluorinated polyimides with moderate to high molecular weights have been prepared by a one-step polycondensation procedure. The resulting polyimides could be readily solution-cast into transparent and flexible films with light color, good optical transparency, moderate to high glass-transition temperatures, and low dielectric constants. The eminent combination of several properties guaranteed the obtained polyimides as potential high-temperature resistant materials for optical and photoelectric applications.

    26. Hydrophilic Modification of Microporous Polysulfone Membrane via Surface-Initiated Atom Transfer Radical Polymerization and Hydrolysis of Poly(glycidylmethacrylate) (pages 2473–2482)

      Chaozhan Wang, Sa Zhao and Yinmao Wei

      Article first published online: 14 AUG 2012 | DOI: 10.1002/cjoc.201200443

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      Comparing with polysulfone (PSF) membrane, the poly(glycidylmethacrylate) (PGMA) grafted membrane has much better antifouling property, and the antifouling property was further improved by hydrolysis of the epoxy groups in the grafting chains.

    27. Novel Synthetic Route to α-Aminophosphonates Containing Benzothiazole Moiety (pages 2483–2487)

      Liju Gu, Rui Wang, Xiangzhong Huang and Cheng Jin

      Article first published online: 23 OCT 2012 | DOI: 10.1002/cjoc.201200831

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      A novel and ef?cient synthetic route to α-aminophosphonates containing benzothiazole moiety via a cascade three-component reaction from conveniently available starting materials has been developed.

    28. Synthesis of 2-Mercaptobenzaldehyde, 2-Mercaptocyclohex-1-enecarboxaldehydes and 3-Mercaptoacrylaldehydes (pages 2495–2500)

      Qingfen Niu, Xiaofeng Xu, Hongjian Sun and Xiaoyan Li

      Article first published online: 14 AUG 2012 | DOI: 10.1002/cjoc.201200433

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      One-pot synthesis of 2-mercaptobenzaldehyde, 2-mercaptocyclohex-1-enecarboxaldehydes and 3-mercaptoacrylaldehydes was developed by the reaction of the Grignard reagent with sulfur. The novel procedure showed high yields of the desired products, easy work-up, short reaction time, no catalyst, no hazardous phosphine ligands, no strong and foul smell sulfur-containing reagents, no environmental problem and mild reaction conditions in comparison with other methods, which are the strong points of the present procedure.

    29. Theoretical Investigation into Electronic Structures and Charge Transfer Properties of π-Conjugated System with Different Combinations of Thiophene and Vinyl/Butadiene (pages 2501–2508)

      Chunmei Zhao, Chunrong Li, Yan Ma, Caibin Zhao and Wenliang Wang

      Article first published online: 14 AUG 2012 | DOI: 10.1002/cjoc.201200444

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      The presence of vinyl and butadiene in thiophene chain leads to many excellent properties. The different combinations of thiophene and vinyl/butadiene are absent in the theoretical calculation. The designed 3c (T5B4) is recommended as the promising ambipolar material for possessing the equal minimum λh (0.24 eV) and λe (0.24 eV). The linear relationships are found between experimental lowest singlet excited energies (Eexp) and theoretical ΔEH-L and Eg.

    30. Synthesis, Crystal Structure and Anticancer Activities of Tetrahydropyrido[4,3-d]dihydropyrimidine-2-thiones (pages 2509–2516)

      Li Ding, Sijia Xue, Jing Li, Di Xiao, Jing Wang, Zhibing Hao and Chuncheng Pang

      Article first published online: 23 OCT 2012 | DOI: 10.1002/cjoc.201200568

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      A new series of tetrahydropyrido[4,3-d]dihydropyrimidine-2-thiones (3a3x) were synthesized and the conformation of compound 3j was confirmed by X-ray diffraction. Preliminary bioassays indicated that most of the target compounds presented good antiproliferative activities against leukemic K562 cells, ovarian cancer HO-8910 cells and liver cancer SMMC-7721 cells in vitro. Preliminary mechanism of action studies revealed that compound 3i caused DNA fragmentation and activated caspase-3/7 in leukemic K562 cells.

    31. Rapid Determination of Free Amino Acids in Milk by Microchip Electrophoresis Coupled with Laser-induced Fluorescence Detection (pages 2517–2521)

      Min Wu, Shuang Cheng, Gang Li, Zhifang Wang, Qingjiang Wang, Pingang He and Yuzhi Fang

      Article first published online: 23 OCT 2012 | DOI: 10.1002/cjoc.201200446

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      Seven kinds of free amino acids usually contained in milk were determined within 150 s by microchip electrophoresis coupled with florescence detection based on Cy5 derivatization.

    32. Synthesis, Bioactivities and Structure Activity Relationship of N-4-Methyl-1,2,3-thiadiazole-5-carbonyl-N′-phenyl Ureas (pages 2522–2532)

      Dandan Guo, Zhiwen Wang, Zhijin Fan, Hui Zhao, Wei Zhang, Jiagao Cheng, Jiaqiang Yang, Qingjun Wu, Youjun Zhang and Qian Fan

      Article first published online: 23 OCT 2012 | DOI: 10.1002/cjoc.201200268

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      29 novel N-4-methyl-1,2,3-thiadiazole-5-carbonyl-N′-phenyl ureas were designed and synthesized. Target compounds exhibit insecticidal activities. Bioassays indicated that compounds V-24 and V-22 exhibit outstanding insecticidal activity against Culex pipiens pallens and Plutella xylostella, respectively. Compound V-11 also has a broad-spectrum of fungicide activity against all the fungi tested. Five compounds show good SAR-inducing activity as well. These results establish basis for both disease and insect control in agricultural practice and novel pesticide development. Structure-activity relationship studies reveal that, with the contour maps based on steric and electrostatic CoMFA coefficients, we can conclude the relationship between the structures and bioactivity and continue the further design of highly active compounds.

    33. Homology Modeling and Molecular Docking Studies of (S)-Scoulerine 9-O-Methyltransferase from Coptis chinensis (pages 2533–2538)

      Qiankun Zhu, Jiayu Zhou, Gan Zhang and Hai Liao

      Article first published online: 27 SEP 2012 | DOI: 10.1002/cjoc.201200384

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      In order to study the interactions of SMT with its substrate and further to understand the catalytic mechanism and substrate specificity, a three dimensional model of SMT from Coptis chinensis was constructed by homology modeling using the crystal structure of caffeic acid/5-hydroxyferulic acid 3/5-O-methyltransferase (COMT) as a template. The three dimensional structure of SMT, which was mainly composed of α-helices and some β-sheets, was similar to that of COMT. In contrast with COMT, the non-conserved residues in the substrate binding pocket of SMT might be responsible for their differences in the substrate specificity. Val119 and Asp254 in SMT were the key residues for orienting substrate for methylation as both residues had H-bonds with (S)-scoulerine. The methylation of (S)-scoulerine involved deprotonation of the 9-hydroxyl group by His253 and Asp254 in SMT followed by a nucleophilic attack on the SAM-methyl resulting in the product, (S)-tetrahydrocolumbamine.

    34. Adsorption and Decomposition Mechanism of 1,1-Diamino-2,2-dinitroethylene on Al(111) Surface by Periodic DFT Calculations (pages 2539–2548)

      Caichao Ye, Xuehai Ju, Fengqi Zhao and Siyu Xu

      Article first published online: 14 AUG 2012 | DOI: 10.1002/cjoc.201200470

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      The adsorption of 1,1-diamino-2,2-dinitroethylene molecule on the Al(111) surface was investigated by the density functional theory (DFT). The largest adsorption energy is −940.5 kJ/mol. The charge transfer is as large as 3.31e from the Al surface to the FOX-7 fragment. The largest activation energy for a dissociation step is 428.8 kJ/mol, while activation energies of other con?gurations are much smaller, in the range of 2.4 to 147.7 kJ/mol.

    35. Immobilization of Antibodies on Magnetic Carbonaceous Microspheres for Selective Enrichment of Lysine-acetylated Proteins and Peptides (pages 2549–2555)

      Yingyin Wang, Jun Yao, Pengyuan Yang, Chunhui Deng and Huizhi Fan

      Article first published online: 23 OCT 2012 | DOI: 10.1002/cjoc.201200542

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      In this study, for the first time, antibody-immobilized magnetic carbonaceous microspheres were developed for selective enrichment of acetylated proteins and peptides. The antibody immobilization strategy had high efficiency and specificity. Meanwhile, owing to the strong magnetism of the materials, the microspheres showed much convenience in operation. In a word, it provides a novel technique and may have more applications in the large-scale proteomic study.

    36. Syntheses, Characterizations and Adsorption Properties of MIL-101/Graphene Oxide Composites (pages 2563–2566)

      Xiaoqing Liu, Hu Zhou, Ying Zhang, Yuanjun Liu and Aihua Yuan

      Article first published online: 23 OCT 2012 | DOI: 10.1002/cjoc.201200575

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      Composites of MIL-101 and grapheme oxide (GO) were prepared with varying ratios of two components. The parent material MIL-101 and composites MIL-GO were characterized by X-ray diffraction, scanning electron microscopy and nitrogen adsorption. The incorporation of GO layers has an obvious impact on the formation of MIL-101 units, the size of crystals and the porosities of composites.

    37. Tetrahydropyranylation of Alcohols and Phenols Using Polystyrene Supported Lewis Acids as Catalysts (pages 2567–2572)

      Yi Zhang, Qianqian Dou, Yuan Liu, Liyan Dai, Xiaozhong Wang and Yingqi Chen

      Article first published online: 23 OCT 2012 | DOI: 10.1002/cjoc.201200713

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      Polystyrene supported TiCl4 (Ps-TiCl4) and polystyrene supported FeCl3 (Ps-FeCl3) were prepared by coordinating Lewis acids with polystyrene. The catalysts were characterized by TGA, BET, SEM, IR and pyridine-adsorbed IR. The loading of Ps-TiCl4 and Ps-FeCl3 were 0.35 and 0.3 mmol·g−1 respectively. Both catalysts were found to be efficient for the tetrahydropyranylation and detetrahydropyranylation of various alcohols and phenols in different solvents. Two catalysts can be recovered and reused for five times with good activity.

    38. Density Functional Theoretical Analysis of the Molecular Structural Effects on Raman Spectra of β-Carotene and Lycopene (pages 2573–2580)

      Weilong Liu, Zhigang Wang, Zhiren Zheng, Lilin Jiang, Yanqiang Yang, Liancheng Zhao and Wenhui Su

      Article first published online: 23 OCT 2012 | DOI: 10.1002/cjoc.201200661

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      The ν1 bands of β-carotene and lycopene shift respectively to higher and lower frequencies in solution compared with those in the solid state due to the release of the crystal packing forces. The B3LYP/6-31G(d) method can predict reasonable Raman spectrum of β-carotene, but the calculated ν1 Raman activity of lycopene overflows. The solvent has slight (significant) effects on the Raman frequencies (intensities) of both carotenoids.

    39. Palladium-Catalyzed Suzuki-Miyaura Type Coupling Reaction of Aryl Halides with Triphenylborane-Pyridine (pages 2581–2586)

      Minghua Yang, Yongbing Gu, Yan Wang, Xiyu Zhao and Guobing Yan

      Article first published online: 23 OCT 2012 | DOI: 10.1002/cjoc.201200775

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      The Suzuki-Miyaura type coupling reaction of aryl halides with triphenylborane-pyridine was described. The reaction can be catalyzed by Pd(OAc)2 (5 mol%) in the presence of Cs2CO3 at 50°C or 80°C, and functionalized biaryls were obtained in good to excellent yields. This protocol is general and can tolerate a wide range of functional groups.

  6. Note

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Communications
    5. Communication
    6. Full Papers
    7. Note
    8. Erratum
    1. Catalytic, Conjugate Reduction-Aldol Addition Reaction of β′-Oxoalkyl α,β-Unsaturated Carboxylates (pages 2587–2590)

      Aijun Zheng, Lan Jiang and Zhengning Li

      Article first published online: 14 AUG 2012 | DOI: 10.1002/cjoc.201200523

      Thumbnail image of graphical abstract

      Catalytic, intramolecular conjugate reduction-aldol addition reactions of β′-oxoalkyl α,β-unsaturated carboxylates were achieved using copper hydride ligated with bis[(2-diphenylphosphino)phenyl] ether catalyst, yielding lactones in moderate to good yields and in high diastereoselectvities.

    2. Group IV M-POSS (M=Zr, Hf) Coordination Polymers (pages 2591–2594)

      Zhijun Wei, Hongbo Ren, Lin Zhang and Meiming Luo

      Article first published online: 23 OCT 2012 | DOI: 10.1002/cjoc.201200696

      Thumbnail image of graphical abstract

      The Zr-POSS and Hf-POSS coordination polymers have been successfully synthesized and charactered.

    3. Facile and Efficient Synthesis of (R)-4-(Benzyloxy)-3-methylbutanenitrile: Toward Developing a Versatile Chiral Building Block (pages 2595–2597)

      Zijie Song, Yong Shi, Ronghua Jin, Jingrong Lin and Weisheng Tian

      Article first published online: 14 AUG 2012 | DOI: 10.1002/cjoc.201200517

      Thumbnail image of graphical abstract

      A practical synthesis of (R)-4-(benzyloxy)-3-methylbutanenitrile, a potential chiral building block, from the corresponding α-keto ester in high yield and large scale was presented.

  7. Erratum

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Communications
    5. Communication
    6. Full Papers
    7. Note
    8. Erratum
    1. You have free access to this content
      Erratum: Synthesis, Insecticidal Assay and Molecular Docking Study of Novel Neonicotinoids N-Oxide Analogues (page 2598)

      Wenwen Zhang, Yefeng Fan, Tao Yu, Zhiping Xu, Xiaoyong Xu, Jiagao Cheng and Zhong Li

      Article first published online: 23 OCT 2012 | DOI: 10.1002/cjoc.201290028

      This article corrects:

      Synthesis, Insecticidal Assay and Molecular Docking Study of Novel Neonicotinoids N-Oxide Analogues

      Vol. 30, Issue 2, 357–361, Article first published online: 23 DEC 2011

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