Chemistry - A European Journal

Cover image for Vol. 18 Issue 1

January 2, 2012

Volume 18, Issue 1

Pages 1–379

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Concept
    8. Minireview
    9. Communications
    10. Full Papers
    11. Preview
    1. You have free access to this content
      Cover Picture: One-Pot Aqueous Solution Syntheses of Iron Oxide Nanostructures with Controlled Crystal Phases through a Microbial-Mineralization-Inspired Approach (Chem. Eur. J. 1/2012) (page 1)

      Dr. Yuya Oaki, Naoki Yagita and Prof. Hiroaki Imai

      Version of Record online: 27 DEC 2011 | DOI: 10.1002/chem.201190271

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      A microbial-mineralization-inspired approach has been used to synthesize iron oxides with controlled oxidation states and crystal phases. The presence of a chelating agent facilitates the control of the oxidation states through a ligand-controlled approach. The control of the crystal phases is achieved by the tuning of the synthetic conditions, such as the initial pH, the concentration of the chelating agent, and the reaction temperature. For more details, see the Full Paper by H. Imai, Y. Oaki et al. on page 110 ff.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Concept
    8. Minireview
    9. Communications
    10. Full Papers
    11. Preview
    1. Inside Cover: Analysis of NAD 2D-NMR Spectra of Saturated Fatty Acids in Polypeptide Aligning Media by Experimental and Modeling Approaches (Chem. Eur. J. 1/2012) (page 2)

      Zeinab Serhan, Andrea Borgogno, Dr. Isabelle Billault, Dr. Alberta Ferrarini and Dr. Philippe Lesot

      Version of Record online: 27 DEC 2011 | DOI: 10.1002/chem.201190273

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      Natural abundance deuterium 2D-NMR (NAD 2D-NMR) experiments in oriented solutions of polypeptides have been used to successfully resolve almost all inequivalent deuterium sites of long-chain saturated fatty acid methyl esters, a crucial step for establishing their natural isotopic profile. Theoretical prediction of quadrupolar splittings confirms the spectral assignments and demonstrates the key role of steric solute/polypeptide interactions for the ordering of fatty acid esters. For more details see the Full Paper by P. Lesot, A. Ferrarini et al. on page 117 ff.

  3. Editorial

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Concept
    8. Minireview
    9. Communications
    10. Full Papers
    11. Preview
    1. Editorial

      You have free access to this content
  4. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Concept
    8. Minireview
    9. Communications
    10. Full Papers
    11. Preview
  5. News

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Concept
    8. Minireview
    9. Communications
    10. Full Papers
    11. Preview
  6. Concept

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Concept
    8. Minireview
    9. Communications
    10. Full Papers
    11. Preview
    1. Phosphorylation

      Current Chemical Biology Tools for Studying Protein Phosphorylation and Dephosphorylation (pages 28–39)

      Candy H. S. Lu, Dr. Kai Liu, Lay Pheng Tan and Prof. Shao Q. Yao

      Version of Record online: 9 DEC 2011 | DOI: 10.1002/chem.201103206

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      Reading the signals: Advanced chemical biology tools are applied in the study of complex phosphoproteome signaling networks (see figure). The recent advances in the development of these tools are highlighted as well as their applications in high-throughput screening.

  7. Minireview

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Concept
    8. Minireview
    9. Communications
    10. Full Papers
    11. Preview
    1. Gas-Phase Chemistry

      Mechanistic Aspects and Elementary Steps of N[BOND]H Bond Activation of Ammonia and C[BOND]N Coupling Induced by Gas-Phase Ions: A Combined Experimental/Computational Exercise (pages 40–49)

      Dipl.-Chem. Robert Kretschmer, Dr. Maria Schlangen and Prof. Dr. Helmut Schwarz

      Version of Record online: 5 DEC 2011 | DOI: 10.1002/chem.201102494

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      Step by step: Due to its extraordinary potential, N[BOND]H bond activation and C[BOND]N coupling processes have formed the focus of broad research activities. This Minireview will describe examples of these processes mediated by gaseous “bare” or ligated ions and provide detailed insights into the underlying mechanisms and elementary steps.

  8. Communications

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Concept
    8. Minireview
    9. Communications
    10. Full Papers
    11. Preview
    1. Biomimetic Synthesis

      A Discrete Five-Coordinate NiIII Complex Resembling the Active Site of the Oxidized Form of Nickel Superoxide Dismutase (pages 50–53)

      Prof. Way-Zen Lee, Chien-Wei Chiang, Tsung-Han Lin and Ting-Shen Kuo

      Version of Record online: 9 DEC 2011 | DOI: 10.1002/chem.201102690

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      Nickel biomimic: A pentadentate ligand, 2,6-bis(((S)-2-(diphenylhydroxymethyl)-1-pyrrolidinyl)methyl)pyridine (H2BDPP), was deprotonated and subsequently reacted with [Ni(CH3CN)6](ClO4)2 to give Ni(BDPP) (1). A square-pyramidal NiIII complex, [Ni(BDPP)](PF6) (2), was obtained via oxidation of 1. Complex 2 can oxidize O2 into O2 and its EPR spectrum is similar to that of the oxidized form of NiSOD.

    2. Phenalenyl Chemistry

      Phenalenyl-Based Molecules: Tuning the Lowest Unoccupied Molecular Orbital to Design a Catalyst (pages 54–58)

      Tamal K. Sen, Arup Mukherjee, Arghya Modak, Dr. Pradip Kr. Ghorai, Daniel Kratzert, Markus Granitzka, Prof. Dr. Dietmar Stalke and Dr. Swadhin K. Mandal

      Version of Record online: 9 DEC 2011 | DOI: 10.1002/chem.201103224

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      Phenalenyl in action: The cationic state of the phenalenyl system can be used to design Lewis acidic catalysts. The phenalenyl backbone can tune the energy of the lowest unoccupied molecular orbital (LUMO) of the molecule, which in turn controls the catalytic activity in the ring-opening polymerization of cyclic esters (see figure).

    3. Polyoxometalates

      An Alkoxido-Tin-Substituted Polyoxometalate [(MeO)SnW5O18]3−: The First Member of a New Family of Reactive {SnW5} Lindqvist-Type Anions (pages 59–62)

      Balamurugan Kandasamy, Dr. Corinne Wills, Prof. William McFarlane, Prof. William Clegg, Dr. Ross W. Harrington, Dr. Antonio Rodríguez-Fortea, Prof. Josep M. Poblet, Prof. Peter G. Bruce and Dr. R. John Errington

      Version of Record online: 6 DEC 2011 | DOI: 10.1002/chem.201103544

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      A SnOW-bound polyoxometalate: Targeted incorporation of {SnOMe}3+ into lacunary {W5O18}6− has been achieved by hydrolytic self-assembly. The [(MeO)SnW5O18]3− ion undergoes a reversible one-electron reduction, shows a large upfield shift of the Wax resonance in the 183W NMR spectrum and has a calculated HOMO–LUMO gap of 3.5 eV. A wide range of {SnW5} derivatives is now accessible by ligand substitution at the Sn centre.

    4. Asymmetric Catalysis

      Core Structure-Based Design of Organocatalytic [3+2]-Cycloaddition Reactions: Highly Efficient and Stereocontrolled Syntheses of 3,3′-Pyrrolidonyl Spirooxindoles (pages 63–67)

      Dr. Bin Tan, Xiaofei Zeng, Wendy Wen Yi Leong, Zugui Shi, Prof. Dr. Carlos F. Barbas III and Prof. Dr. Guofu Zhong

      Version of Record online: 9 DEC 2011 | DOI: 10.1002/chem.201103449

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      Extraordinary levels of stereocontrol were achieved in an efficient organocatalytic asymmetric [3+2]-cycloaddition reaction between an α-isothiocyanato imide and various methyleneindolinones. Simple precursors were used for the rapid construction of spirocyclic oxindole derivatives with high enantiopurity and structural diversity, thus providing a new avenue of significance to medicinal chemistry and diversity-oriented synthesis.

    5. Organic Synthesis

      N-Fused Indolines through Non-Carbonyl-Stabilized Rhodium Carbenoid C[BOND]H Insertion of N-Aziridinyl Imines (pages 68–71)

      Stuart J. Mahoney and Prof. Dr. Eric Fillion

      Version of Record online: 8 DEC 2011 | DOI: 10.1002/chem.201103155

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      Under rhodium catalysis, N-aziridinyl imines provided access to N-fused indolines through non-carbonyl-stabilized rhodium carbenoid C[BOND]H insertion. The utility of this methodology for the synthesis of architecturally complex heterocycles was further demonstrated by an expedient total synthesis of (±)-cryptaustoline (see scheme).

    6. Carbon Dioxide Fixation

      Catalytic Hydrogenation of Carbon Dioxide and Bicarbonates with a Well-Defined Cobalt Dihydrogen Complex (pages 72–75)

      Christopher Federsel, Carolin Ziebart, Dr. Ralf Jackstell, Dr. Wolfgang Baumann and Prof. Dr. Matthias Beller

      Version of Record online: 6 DEC 2011 | DOI: 10.1002/chem.201101343

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      (Co)balt upright: A well-defined cobalt dihydrogen complex is shown to be an active catalyst for the hydrogenation of CO2 and bicarbonates (see figure), giving the highest turnover numbers so far for any non-precious-metal-based catalyst.

    7. Asymmetric Catalysis

      You have full text access to this OnlineOpen article
      Enantioselective One-Pot Synthesis of α-Amino Esters by a Phosphine-Catalyzed [3+2]-Cycloaddition Reaction (pages 76–79)

      Dr. Marianne Steurer, Kim L. Jensen, Dr. Dennis Worgull and Prof. Dr. Karl Anker Jørgensen

      Version of Record online: 7 DEC 2011 | DOI: 10.1002/chem.201103502

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      Phosphines go one-pot: The one-pot synthesis of cyclic α-amino esters from azlactones and allenes by a phosphine-catalyzed [3+2]-cycloaddition reaction followed by a ring opening of the azlactone moiety is presented. The products are isolated as single regioisomers in good overall yields and high enantioselectivities (up to 95 % ee). The possibility for easy modifications of the obtained products was demonstrated by synthesizing an amino acid and an α-hydroxy-β-ketoester.

    8. The Origins of Enantioselectivity in Rh–Diene Complex Catalysed Arylation of Cyclohex-2-enones (pages 80–84)

      Dr. Silvia Gosiewska, Dr. Jevgenij A. Raskatov, Dr. Ryo Shintani, Prof. Tamio Hayashi and Dr. John M. Brown

      Version of Record online: 12 DEC 2011 | DOI: 10.1002/chem.201102421

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      Chiral diene ligands: Conjugate addition of aryl boronic acids to cyclohexenone is catalysed by Rh complexes of the simple chiral diene (S)-bicyclo[3.3.1]nona-2,6-diene in unexpectedly high ee. Insight into the reasons, and more generally the TS structure and pathways with other catalysts, was explored by using density functional theory. There was a gratifyingly good agreement between calculation and experiment. A lack of obvious steric discrimination together with systematic variations in TS structure implicated stereoelectronics.

    9. From the Feist–Bénary Reaction to Organocatalytic Domino Michael–Alkylation Reactions: Asymmetric Synthesis of 3(2 H)-Furanones (pages 85–89)

      Xiaowei Dou, Xiaoyu Han and Prof. Dr. Yixin Lu

      Version of Record online: 12 DEC 2011 | DOI: 10.1002/chem.201102796

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      It all adds up! A modified Feist–Bénary reaction employing a domino Michael–alkylation sequence was designed for the enantioselective synthesis of 3(2 H)-furanones. L-Threonine-derived tertiary amine/thiourea catalysts were prepared for the first time; such catalysts promoted the designed domino Michael–alkylation reactions in a highly enantioselective manner (see scheme).

    10. Synthetic Methods

      Catalytic Selective Oxyamidation of Cyclic Enamides using Nitrenes (pages 90–94)

      Nicolas Gigant, Geoffroy Dequirez, Dr. Pascal Retailleau, Prof. Isabelle Gillaizeau and Dr. Philippe Dauban

      Version of Record online: 8 DEC 2011 | DOI: 10.1002/chem.201102302

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      Yes, nitrenes did “N,O”! Intermolecular addition of nitrene to enecarbamates and enesulfonamides gives oxyamidated products in excellent yields of up to 98 % and with good levels of stereoselectivity. Complete regioselectivity is also observed, leading to the formation of N,O-acetals which can further react with various nucleophiles under acidic conditions (see scheme; TcesNH2=trichloroethylsulfamate).

  9. Full Papers

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Concept
    8. Minireview
    9. Communications
    10. Full Papers
    11. Preview
    1. Luminescent Materials

      Luminescent Organoplatinum(II) Complexes with Functionalized Cyclometalated C^N^C Ligands: Structures, Photophysical Properties, and Material Applications (pages 96–109)

      Dr. Steven C. F. Kui, Faan-Fung Hung, Dr. Shiu-Lun Lai, Dr. Mai-Yan Yuen, Dr. Chi-Chung Kwok, Dr. Kam-Hung Low, Dr. Stephen Sin-Yin Chui and Prof. Chi-Ming Che

      Version of Record online: 14 DEC 2011 | DOI: 10.1002/chem.201101880

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      The bright lights! New luminescent platinum(II) complexes with carbazole, fluorene or thiophene unit(s) at the periphery of the C N C ligands have been synthesized (see scheme). Among these complexes, [(L)Pt(C[TRIPLE BOND]N{2,6-(CH3)2C6H3})] (L=ligand with thiophene) has the highest emission quantum yield (0.26) in CH2Cl2. The uses of these complexes in the generation of 1O2, formation of nanostructures, and fabrication of high-efficiency red OLEDs are highlighted.

    2. Biomimetic Synthesis

      One-Pot Aqueous Solution Syntheses of Iron Oxide Nanostructures with Controlled Crystal Phases through a Microbial-Mineralization-Inspired Approach (pages 110–116)

      Dr. Yuya Oaki, Naoki Yagita and Prof. Hiroaki Imai

      Version of Record online: 5 DEC 2011 | DOI: 10.1002/chem.201102663

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      A natural inspiration: A microbial-mineralization-inspired approach for the syntheses of iron oxides has been developed in an aqueous solution at low temperature. The presence of a chelating agent and the tuning of the reaction conditions lead to the formation of iron oxides with controlled oxidation states and crystal phases (see figure).

    3. Analytical Chemistry

      Analysis of NAD 2D-NMR Spectra of Saturated Fatty Acids in Polypeptide Aligning Media by Experimental and Modeling Approaches (pages 117–126)

      Zeinab Serhan, Andrea Borgogno, Dr. Isabelle Billault, Dr. Alberta Ferrarini and Dr. Philippe Lesot

      Version of Record online: 12 DEC 2011 | DOI: 10.1002/chem.201102775

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      Fatty acids—oriented but not slimmed: The analysis C14 to C18 fatty acids by using natural abundance deuterium 2D-NMR in polypeptide liquid crystals has been achieved. Almost all 2H sites of solutes could be resolved. Assignment of quadrupolar doublets was achieved by an experimental strategy combining various sources of information, and was confirmed by a theoretical model predicting the anisotropic distribution of fatty acids in the polypeptide solution (see figure).

    4. Kinetics

      Nucleophilic Reactivities of the Anions of Nucleobases and Their Subunits (pages 127–137)

      Dr. Martin Breugst, M. Sc. Francisco Corral Bautista and Prof. Dr. Herbert Mayr

      Version of Record online: 8 DEC 2011 | DOI: 10.1002/chem.201102411

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      The kinetics of the reactions of the anions of imidazoles, purines, pyrimidines, and related compounds with benzhydrylium ions and structurally related quinone methides have been investigated in aqueous and DMSO solution. The resulting rate constants follow the correlation log k2=sN (N + E), which allowed us to derive their reactivity parameters N and sN.

    5. Oxygen Atom Transfer

      Oxygen Atom Transfer from a trans-Dioxoruthenium(VI) Complex to Nitric Oxide (pages 138–144)

      Dr. Wai-Lun Man, Dr. William W. Y. Lam, Siu-Mui Ng, Wenny Y. K. Tsang and Prof. Tai-Chu Lau

      Version of Record online: 2 DEC 2011 | DOI: 10.1002/chem.201102297

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      Reduction of [RuVI(L)(O)2]2+ to [Ru(L)(NO)(OH)]2+ by NO was accomplished in aqueous solution and CH3CN. The reaction involves two steps. Mechanistic studies indicate that the first step occurs by initial O atom transfer from [RuVI(L)(O)2]2+ to NO, whereas the second step occurs by initial one-electron O transfer from [RuIV(L)(O)]2+ to NO (see scheme). This is the first example of O atom transfer from an oxometal species to NO.

    6. Pd-Catalyzed Reactions

      Amination with Pd[BOND]NHC Complexes: Rate and Computational Studies Involving Substituted Aniline Substrates (pages 145–151)

      Ka Hou Hoi, Dr. Selçuk Çalimsiz, Dr. Robert D. J. Froese, Prof. Alan C. Hopkinson and Prof. Michael G. Organ

      Version of Record online: 2 DEC 2011 | DOI: 10.1002/chem.201102428

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      The amination of chloroarenes with substituted aniline derivatives was examined with the diisopropyl- (IPr) and diisopentylphenylimidazolium (IPent) N-heterocyclic carbene(NHC)–Pd complexes. Anilines substituted with electron-rich groups couple faster than electron-poor ones suggesting that deprotonation is not problematic, as is the case with secondary amines that are electron rich. Computational studies predict that the IPent precatalyst is more reactive than IPr for amination with anilines, which was also found to be the case in rate studies.

    7. Metal–Organic Frameworks

      Three-Dimensional Porous Metal–Radical Frameworks Based on Triphenylmethyl Radicals (pages 152–162)

      Dr. Angela Datcu, Dr. Nans Roques, Dr. Véronique Jubera, Dr. Daniel Maspoch, Dr. Xavier Fontrodona, Dr. Klaus Wurst, Dr. Inhar Imaz, Georges Mouchaham, Dr. Jean-Pascal Sutter, Prof. Concepció Rovira and Prof. Jaume Veciana

      Version of Record online: 8 DEC 2011 | DOI: 10.1002/chem.201102278

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      A rare find: MOFs that combine a fairly rare (6,3) connectivity and large 1D channels were obtained by reacting LnIII ions (Ln=Tb, Gd, Eu) with open- or closed-shell perchlorinated triphenylmethyl (PTM) ligands (see picture). Tb and Eu compounds based on the diamagnetic ligand show metal-centered luminescence. In radical-based complexes, {Ln-Radical; Ln=Tb, Gd} the interactions were found to be ferromagnetic.

    8. Laser Chemistry

      General Bottom-Up Construction of Spherical Particles by Pulsed Laser Irradiation of Colloidal Nanoparticles: A Case Study on CuO (pages 163–169)

      Dr. Hongqiang Wang, Dr. Kenji Kawaguchi, Dr. Alexander Pyatenko, Dr. Xiangyou Li, Dr. Zaneta Swiatkowska-Warkocka, Yukiko Katou and Dr. Naoto Koshizaki

      Version of Record online: 2 DEC 2011 | DOI: 10.1002/chem.201102079

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      Laser faire: A general laser processing technique for the synthesis of semiconductor/metal colloidal spheres has been investigated; the selective pulsed heating assures the formation of spherical particles. The size and phase of resultant colloidal spheres are controlled by the input laser fluence (see figure). The heating–melting–fusion mechanism is thought to be responsible for the formation and size evolution of the colloidal spheres.

    9. Carboxylation

      Carboxylation of Arene C[BOND]H Bonds with CO2: A DFT-Based Approach to Catalyst Design (pages 170–177)

      Dipl.-Chem. Andreas Uhe, Dr. Markus Hölscher and Prof. Dr. Walter Leitner

      Version of Record online: 5 DEC 2011 | DOI: 10.1002/chem.201102785

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      A quick fix: The direct carboxylation of unactivated arene C[BOND]H bonds with CO2 using ruthenium(II) pincer complexes as catalysts is investigated by DFT methods (see scheme). The turnover frequencies of various catalyst modifications are predicted and optimized catalyst systems are designed.

    10. DNA Nanostructures

      Tandem Arrays of TEMPO and Nitronyl Nitroxide Radicals with Designed Arrangements on DNA (pages 178–183)

      Hiroshi Atsumi, Dr. Kensuke Maekawa, Dr. Shigeaki Nakazawa, Prof. Dr. Daisuke Shiomi, Prof. Dr. Kazunobu Sato, Prof. Dr. Masahiro Kitagawa, Prof. Dr.  Takeji Takui and Prof. Dr. Kazuhiko Nakatani

      Version of Record online: 2 DEC 2011 | DOI: 10.1002/chem.201102693

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      Tandem spin arrays: The formation of one-dimensional electron-spin arrays that consist of two different organic radicals with the arrangement explicitly controlled by the DNA sequence has been described. Two mismatch-binding ligands, which carry 2,2,6,6- tetramethylpiperidine N-oxide (TEMPO) and nitronyl nitroxide, selectively bind to the predetermined sites on double-stranded DNA. By using the two mismatch-binding ligands, electron-spin assembly could be successfully synchronized with the hybridization.

    11. Conformational Analysis

      Modelling Zwitterions in Solution: 3-Fluoro-γ-aminobutyric Acid (3F-GABA) (pages 184–195)

      Dr. Jie Cao, M. Sc. Ragnar Bjornsson, Prof. Dr. Michael Bühl, Prof. Dr. Walter Thiel and Dr. Tanja van Mourik

      Version of Record online: 8 DEC 2011 | DOI: 10.1002/chem.201101674

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      Microsolvation by as many as five water molecules and immersion in a polarisable continuum (PCM) is not sufficient to stabilise the extended conformation of the zwitterionic neurotransmitter analogue, 3F-GABA, over folded conformers. Full explicit modelling of the aqueous solution in a QM/MM-molecular dynamics scheme affords the correct stability order, as confirmed by observed and computed NMR spin–spin coupling constants.

    12. Multichromophoric Arrays

      DNA-Templated Assembly of Naphthalenediimide Arrays (pages 196–201)

      Prof. Mitsunobu Nakamura, Tsukasa Okaue, Dr. Tadao Takada and Prof. Kazushige Yamana

      Version of Record online: 28 NOV 2011 | DOI: 10.1002/chem.201102216

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      It stacks up: A naphthalenediimide (NDI) derivative (1) with two ZnII–cyclens that act as receptors for the thymine base in DNA has been synthesized. UV/Vis and CD spectroscopy, gel filtration, and molecular-modeling studies have shown that the bis(ZnII–cyclen)–NDI can be assembled in the presence of oligo-dT to form π-stacked NDI arrays (see scheme).

    13. Donor–Acceptor Systems

      Donor–Acceptor Ring-in-Ring Complexes (pages 202–212)

      Dr. Ross S. Forgan, Dr. Cheng Wang, Dr. Douglas C. Friedman, Dr. Jason M. Spruell, Charlotte L. Stern, Dr. Amy A. Sarjeant, Dennis Cao and Prof. J. Fraser Stoddart

      Version of Record online: 12 DEC 2011 | DOI: 10.1002/chem.201102919

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      Ringing the changes: Three donor–acceptor ring-in-ring complexes have been prepared as intermediates in the stepwise synthesis of molecular Borromean rings (see figure). Characterization of the complexes in the solution and solid states reveals their stabilities are dictated by CH⋅⋅⋅O contacts as well as by donor–acceptor interactions.

    14. Molecular Recognition

      Molecular Recognition at the Active Site of Factor Xa: Cation–π Interactions, Stacking on Planar Peptide Surfaces, and Replacement of Structural Water (pages 213–222)

      Laura M. Salonen, Mareike C. Holland, Philip S. J. Kaib, Dr. Wolfgang Haap, Dr. Jörg Benz, Jean-Luc Mary, Olivier Kuster, Dr. W. Bernd Schweizer, Dr. David W. Banner and Prof. Dr. François Diederich

      Version of Record online: 9 DEC 2011 | DOI: 10.1002/chem.201102571

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      Factor Xa is an ideal enzyme to undertake molecular recognition studies at atomic level resolution as its active site is completely conserved in complexes with designed ligands. Cation–π interactions, water replacements, and stacking interactions with flat peptide fragments were investigated, revealing large changes in binding affinity resulting from single-atom mutations or positional shifts of heteroatoms in the ligands.

    15. Dendrimers

      Accessing Lipophilic Ligands in Dendrimer-Based Amphiphilic Supramolecular Assemblies for Protein-Induced Disassembly (pages 223–229)

      Volkan Yesilyurt, Rajasekharreddy Ramireddy, Malar A. Azagarsamy and Prof.  S. Thayumanavan

      Version of Record online: 30 NOV 2011 | DOI: 10.1002/chem.201102727

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      Supramolecular disassembly: Although lipophilic ligands on hydrophobic faces of facially amphiphilic dendrimers are hidden within the supramolecular assemblies, the equilibrium between dendritic monomer and amphiphilic aggregate provides a viable pathway for disassembly. Binding-induced disassembly (see scheme) by using lipophilic ligands significantly enhances the scope of protein-based disassembly strategies.

    16. Metal Dissolution

      In Situ Scanning Electrochemical Microscopy (SECM) Detection of Metal Dissolution during Zinc Corrosion by Means of Mercury Sphere-Cap Microelectrode Tips (pages 230–236)

      Prof. Dr. Ricardo M. Souto, Dr. Yaiza González-García, Dr. Dario Battistel and Prof. Dr. Salvatore Daniele

      Version of Record online: 30 NOV 2011 | DOI: 10.1002/chem.201102325

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      Zincing cap: Nucleation and growth of metals on a microelectrode tip led to the continuous modification of the active surface area of the electrode during scanning electrochemical microscopy (SECM) measurements. This was the motivation to explore alternate electrode materials, such as an Hg sphere-cap tip, to detect zinc ions with SECM during corrosion of the metal (see figure).

    17. Metal–Organic Frameworks

      A Metal–Organic Framework with Highly Polar Pore Surfaces: Selective CO2 Adsorption and Guest-Dependent On/Off Emission Properties (pages 237–244)

      Prakash Kanoo, Ashta Chandra Ghosh, Soumya T. Cyriac and Dr. Tapas Kumar Maji

      Version of Record online: 5 DEC 2011 | DOI: 10.1002/chem.201101183

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      Polar pore club: A new 3D microporous metal–organic framework with pore surfaces decorated with open ZnII sites and pendant hydroxyl groups from a dihydroxyterphthalate (H2dht) linker has been synthesised (see figure). It shows highly selective adsorption of CO2 gas at 195 K and exhibits guest induced on/off emission.

    18. Fluorescent Probes

      Site-Specific Control of N7–Metal Coordination in DNA by a Fluorescent Purine Derivative (pages 245–254)

      Anaëlle Dumas and Prof. Dr. Nathan W. Luedtke

      Version of Record online: 5 DEC 2011 | DOI: 10.1002/chem.201102349

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      Chelation control: 8-(2-Pyridyl)-2′-deoxyguanosine (2PyG) acts as a selective bidentate ligand for transition-metal ions (see figure). Upon incorporation into DNA, 2PyG directs metal ions to specific N7 sites in duplex and G-quadruplex structures; this enables thermodynamic analyses of site-specific metal-ion-binding interactions that have hitherto been impossible to conduct. Changes in 2PyG fluorescence provide a direct readout of N7–metal binding.

    19. Gallium Catalysis

      Addition of Alkynes to a Gallium Bis-Amido Complex: Imitation of Transition-Metal-Based Catalytic Systems (pages 255–266)

      Prof. Dr. Igor L. Fedushkin, Alexander S. Nikipelov, Dr. Alexander G. Morozov, Dr. Alexandra A. Skatova, Anton V. Cherkasov and Prof. Dr. Gleb A. Abakumov

      Version of Record online: 2 DEC 2011 | DOI: 10.1002/chem.201102243

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      Go Ga-Ga for gallium! Alkynes add to the bis-gallium complex (dpp-bian)Ga–Ga(dpp-bian) (1) at room temperature. Complex 1 is an effective catalyst for hydroamination and hydroarylation of phenylacetylene with anilines (see scheme).

    20. Metal–Organic Frameworks

      Construction of Metal–Organic Frameworks: Versatile Behaviour of a Ligand Containing Mono- and Bidentate Coordination Sites (pages 267–276)

      Dr. Tia Jacobs and Dr. Michaele J. Hardie

      Version of Record online: 2 DEC 2011 | DOI: 10.1002/chem.201101998

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      soc it and see: Trischelate and monochelate metal complexes of a decorated 2,2′-bipyridine ligand are effective structural nodes or building units for the construction of three- or two-dimensional coordination polymer materials. The three-dimensional structure has a highly unusual {44⋅62}3{46⋅89}2soc topology, which can also be described as vertex-sharing stella octangula prisms with large channels and cavities.

    21. Electrochemistry

      Electrolysis of Water in the Diffusion Layer: First-Principles Molecular Dynamics Simulation (pages 277–282)

      M. Sc. Florian Hofbauer and Prof. Dr. Irmgard Frank

      Version of Record online: 8 DEC 2011 | DOI: 10.1002/chem.201002094

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      Electrochemistry on the fly: The reactions occurring during water electrolysis in the outer Helmholtz layer are investigated using Car–Parrinello molecular dynamics. A complex reaction scheme involving radical and ionic intermediates is observed.

    22. Self-Assembled Monolayers

      Electroactive Self-Assembled Monolayers of Unique Geometric Structures by Using Rigid Norbornylogous Bridges (pages 283–292)

      Dr. Nadim Darwish, Dr. Paul K. Eggers, Dr. Paulo Da Silva, Dr. Yi Zhang, Dr. Yujin Tong, Prof. Shen Ye, Prof. Dr. J. Justin Gooding and Prof. Dr. Michael N. Paddon-Row

      Version of Record online: 23 NOV 2011 | DOI: 10.1002/chem.201101588

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      Building bridges: Rigid anthraquinone-terminated norbornylogous bridges (NBs) have been synthesized and used to form monolayers in which the redox moiety has a well-defined distance and orientation from the electrode surface. Each NB molecule attaches to the electrode surface through two CH2SH groups in a trans relationship. Straight (S) and L-shaped (L) NBs place the anthraquinone moiety close to the surface normal and tangent, respectively (see figure).

    23. Supramolecular Complexes

      A Self-Assembled Complex with a Titanium(IV) Catecholate Core as a Potential Bimodal Contrast Agent (pages 293–302)

      Geert Dehaen, Dr. Svetlana V. Eliseeva, Dr. Kristof Kimpe, Dr. Sophie Laurent, Prof. Luce Vander Elst, Prof. Robert N. Muller, Prof. Wim Dehaen, Prof. Koen Binnemans and Prof. Tatjana N. Parac-Vogt

      Version of Record online: 2 DEC 2011 | DOI: 10.1002/chem.201101413

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      Let's get photophysical: This work deals with the design and investigation of relaxometric and photophysical properties of a self-assembled supramolecular complex that contains three Ln-DTPA-catechol (DTPA=diethylenetriamine-N,N,N′,N′′,N′′-pentaacetate) moieties around a central TiIV core (see figure).

    24. Molecular Imprinting

      Hydrogel Photonic Sensor for the Detection of 3-Pyridinecarboxamide (pages 303–309)

      Yanxia Yuan, Zhiliang Li, Yue Liu, Prof. Dr. Jianping Gao, Zeng Pan and Prof. Dr. Yu Liu

      Version of Record online: 2 DEC 2011 | DOI: 10.1002/chem.201102001

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      Sensor and sensibility: A sensor for the efficient detection of 3-pyridinecarboxamide (PA) in aqueous solution was developed by combining photonic colloid templating and molecular imprinting. It demonstrates a convenient, fast, and sensitive response to PA. A remarkable shift of over 182 nm from λ=440 to 622 nm is observed in 6 % 3-pyridinecarboxamide solutions (see figure).

    25. Microporous Materials

      Photopolymerized Polypyrrole Microvessels (pages 310–320)

      Krystyna Kijewska, Prof. Gary J. Blanchard, Dr. Jakub Szlachetko , Prof. Jarosław Stolarski, Dr. Anna Kisiel, Dr. Agata Michalska, Prof. Krzysztof Maksymiuk, Dr. Marcin Pisarek, Paweł Majewski, Prof. Paweł Krysiński and Dr. Maciej Mazur

      Version of Record online: 5 DEC 2011 | DOI: 10.1002/chem.201101400

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      Polymer microvessels: Microvessels were fabricated by UV-induced polymerization of pyrrole onto the surface of aqueous droplets. The aqueous core allows entrapment of several hydrophilic species, including fluorescent dyes, magnetic nanoparticles, and inorganic ions (see figure).

    26. Nucleophilic Substitution

      Do Glycosyl Sulfonium Ions Engage in Neighbouring-Group Participation? A Study of Oxathiane Glycosyl Donors and the Basis for their Stereoselectivity (pages 321–333)

      Dr. Martin A. Fascione, Colin A. Kilner, Dr. Andrew G. Leach and Dr. W. Bruce Turnbull

      Version of Record online: 2 DEC 2011 | DOI: 10.1002/chem.201101889

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      SN2 good to be true? The reactivity and stereoselectivity of a family of oxathiane glycosyl donors are reported, highlighting the importance of a ketal group in the oxathiane ring for achieving complete α stereoselectivity. A combination of experiment and ab initio calculations indicates that trends in stereoselectivity across a series of compounds are more consistent with selective addition to oxacarbenium ions rather than a shift between SN1 and SN2 mechanisms (see scheme).

    27. Polymers

      Controlling Conformations in Alternating Dialkylsilylene-Spaced Donor–Acceptor Copolymers by a Cooperative Thorpe–Ingold Effect and Polymer Folding (pages 334–346)

      Dr. Chih-Hsien Chen, Yen-Chin Huang, Wei-Chih Liao, Prof. Tsong-Shin Lim, Kuan-Lin Liu, Prof. I-Chia Chen and Prof. Tien-Yau Luh

      Version of Record online: 8 DEC 2011 | DOI: 10.1002/chem.201102032

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      The bulkiness of the substituents on the silicon atoms (i.e., Me versus iPr) in a series of dialkylsilylene-spaced copolymers may exert the Thorpe–Ingold effect on the local conformation (see picture). The differences in the small energetic barriers for each of the conformational states may be amplified by extending the distance of the folding structure, which results in perturbing the conformation of the polymers.

    28. Folding of Alternating Dialkylsilylene-Spaced Donor–Acceptor Copolymers: The Oligomer Approach (pages 347–354)

      Dr. Chih-Hsien Chen, Wen-Hao Chen, Yi-Hung Liu, Prof. Tsong-Shin Lim and Prof. Tien-Yau Luh

      Version of Record online: 8 DEC 2011 | DOI: 10.1002/chem.201102031

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      Size control: A series of oligomers containing alternating donor and acceptor (2:1) chromophores separated by diisopropylsilylene moieties were synthesized to scrutinize the folding behavior of the corresponding polymers. The photophysical properties of the tetramer approach those of corresponding diisopropylsilylene-containing polymers, whereas those of monomer and dimer behave similarly to those of dimethylsilylene-incorporated polymers. Both the Thorpe–Ingold effect and folding of polymers may be responsible for this behavior (see picture).

    29. Photocrosslinking

      Photocrosslinking between Peptide–Peptide or Peptide–Oligonucleotide by RuII–TAP Complexes (pages 355–364)

      Jonathan Ghesquière, Dr. Nicolas Gauthier, Dr. Julien De Winter, Prof. Pascal Gerbaux, Prof. Cécile Moucheron, Prof. Eric Defrancq and Prof. Andrée Kirsch-De Mesmaeker

      Version of Record online: 2 DEC 2011 | DOI: 10.1002/chem.201101458

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      This is spiral TAP: [Ru(TAP)3]2+ and [Ru(TAP)2(phen)]2+ under visible illumination in the presence of Trp- or Trp-containing tripeptides are able to generate a bi-adduct of these amino acid species to the same complex. This addition of two tripeptides gives rise to an irreversible photobridging between these species tethered to each strand of an oligonucleotide duplex used as the template (see scheme).

    30. Antibacterial Textiles

      Sonochemical Coating of Cotton and Polyester Fabrics with “Antibacterial” BSA and Casein Spheres (pages 365–369)

      Ulyana Shimanovich, Prof. Artur Cavaco-Paulo, Prof. Yeshayahu Nitzan and Prof. Aharon Gedanken

      Version of Record online: 30 NOV 2011 | DOI: 10.1002/chem.201100781

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      Antibacterial-coated fibers: Ultrasonic waves can be used to coat the surfaces of cotton and polyester fabrics with drug-loaded proteinaceous microspheres of bovine serum albumin and casein. The microbubbles were created and anchored onto the fabrics (see figure) in a one-step reaction.

    31. Anisotropic Effects

      Is the Conventional Interpretation of the Anisotropic Effects of C[DOUBLE BOND]C Double Bonds and Aromatic Rings in NMR Spectra in Terms of the π-Electron Shielding/Deshielding Contributions Correct? (pages 370–376)

      Prof. Dr. Marija Baranac-Stojanović, Dr. Andreas Koch and Prof. Dr. Erich Kleinpeter

      Version of Record online: 2 DEC 2011 | DOI: 10.1002/chem.201101882

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      Origin-al thinking: Dissection of computed isotropic shieldings along the Cartesian axes for ethene, cyclobutadiene, benzene, naphthalene, and benzocyclobutadiene show that σ electrons deshield the in-plane region, while π electrons shield this area.

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      Version of Record online: 27 DEC 2011 | DOI: 10.1002/chem.201190274

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