Angewandte Chemie International Edition

Cover image for Vol. 51 Issue 1

January 2, 2012

Volume 51, Issue 1

Pages 1–276

  1. Cover Picture

    1. Top of page
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    3. Inside Cover
    4. Inside Back Cover
    5. Back Cover
    6. Editorial
    7. Graphical Abstract
    8. Flashback
    9. News
    10. Author Profile
    11. News
    12. Book Review
    13. Highlights
    14. Essay
    15. Minireview
    16. Review
    17. Communications
    18. And Finally
    19. Preview
    1. Cover Picture: A Diagonal Approach to Chemical Recycling of Carbon Dioxide: Organocatalytic Transformation for the Reductive Functionalization of CO2 (Angew. Chem. Int. Ed. 1/2012) (page 1)

      Christophe Das Neves Gomes, Dr. Olivier Jacquet, Dr. Claude Villiers, Dr. Pierre Thuéry, Dr. Michel Ephritikhine and Dr. Thibault Cantat

      Article first published online: 6 OCT 2011 | DOI: 10.1002/anie.201106864

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      A blooming tree illustrates how CO2 can be recycled to a variety of chemicals based on a strategy discussed by T. Cantat and co-workers in their Communication on page 187 ff. The approach relies on the simultaneous use of a functionalizing reagent and a reductant that can be independently adjusted to access a variety of molecules from CO2. The direct conversion of CO2, amines, and silanes to formamides is reported.

  2. Inside Cover

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    4. Inside Back Cover
    5. Back Cover
    6. Editorial
    7. Graphical Abstract
    8. Flashback
    9. News
    10. Author Profile
    11. News
    12. Book Review
    13. Highlights
    14. Essay
    15. Minireview
    16. Review
    17. Communications
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    1. Inside Cover: [16]Cloverphene: a Clover-Shaped cata-Condensed Nanographene with Sixteen Fused Benzene Rings (Angew. Chem. Int. Ed. 1/2012) (page 2)

      Dr. José M. Alonso, Dr. Alba E. Díaz-Álvarez, Alejandro Criado, Dr. Dolores Pérez, Dr. Diego Peña and Prof. Dr. Enrique Guitián

      Article first published online: 15 NOV 2011 | DOI: 10.1002/anie.201107584

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      Cloverphenes are graphene-type polyarenes, the structures of which resemble the threefold symmetry of clover leafs. In their Communication on page 173 ff., D. Peña and co-workers present the synthesis and properties of a nanosized [16]cloverphene derivative, which consists of 16 fused benzene rings (22 benzene rings in total) and 102 sp2-hybridized atoms. The synthesis involves sequential [4+2] and [2+2+2] aryne cycloadditions.

  3. Inside Back Cover

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    6. Editorial
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    8. Flashback
    9. News
    10. Author Profile
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    12. Book Review
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    14. Essay
    15. Minireview
    16. Review
    17. Communications
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    1. Inside Back Cover: Electrodeposition of Single-Metal Nanoparticles on Stable Protein 1 Membranes: Application of Plasmonic Sensing by Single Nanoparticles (Angew. Chem. Int. Ed. 1/2012) (page 277)

      Li-Xia Qin, Dr. Yang Li, Dr. Da-Wei Li, Chao Jing, Bao-Qin Chen, Wei Ma, Dr. Arnon Heyman, Prof. Oded Shoseyov, Prof. Itamar Willner, Prof. He Tian and Prof. Yi-Tao Long

      Article first published online: 8 DEC 2011 | DOI: 10.1002/anie.201108161

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      The growth of metal nanoparticles on ion-channel pores of a stable protein 1 (SP1) membrane is monitored in situ by dark field microscopy and plasmon resonance Rayleigh scattering. In their Communication on page 140 ff., Y.-T. Long and co-workers describe the electrodeposition process of single nanoparticles in the core of an SP1 template and the sensing of antigen–antibody binding on single nanoparticles.

  4. Back Cover

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    8. Flashback
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    10. Author Profile
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    12. Book Review
    13. Highlights
    14. Essay
    15. Minireview
    16. Review
    17. Communications
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    1. Back Cover: Design of a Silver–Cerium Dioxide Core–Shell Nanocomposite Catalyst for Chemoselective Reduction Reactions (Angew. Chem. Int. Ed. 1/2012) (page 278)

      Dr. Takato Mitsudome, Dr. Yusuke Mikami, Motoshi Matoba, Dr. Tomoo Mizugaki, Prof. Dr. Koichiro Jitsukawa and Prof. Dr. Kiyotomi Kaneda

      Article first published online: 7 NOV 2011 | DOI: 10.1002/anie.201107546

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      The chemoselective reduction of epoxides to the corresponding alkenes occurs in the presence of an Ag–CeO2 nanoparticle core–shell nanocomposite (AgNPs@CeO2, represented as the moon orbiting the earth) and H2. In their Communication on page 136 ff., K. Kaneda and co-workers report how the chemoselective reaction, which can also be applied to nitrostyrenes, proceeds more efficiently with AgNPs@CeO2 than with conventional oxide-supported metal nanoparticles.

  5. Editorial

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    12. Book Review
    13. Highlights
    14. Essay
    15. Minireview
    16. Review
    17. Communications
    18. And Finally
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  6. Graphical Abstract

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    1. Graphical Abstract: Angew. Chem. Int. Ed. 1/2012 (pages 11–25)

      Article first published online: 29 DEC 2011 | DOI: 10.1002/anie.201190111

  7. Flashback

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    14. Essay
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    1. 50 Years Ago ... (page 22)

      Article first published online: 29 DEC 2011 | DOI: 10.1002/anie.201108448

  8. News

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    14. Essay
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  9. Author Profile

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    1. Herbert Mayr (pages 34–35)

      Article first published online: 1 DEC 2011 | DOI: 10.1002/anie.201106108

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      “The greatest scientific advance of the last decade can only be recognized after another 50 years. The biggest challenge facing scientists is storage of energy …” This and more about Herbert Mayr can be found on page 34.

  10. News

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  11. Book Review

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    1. Much Ado About (Practically) Nothing. A History of the Noble Gases. By David E. Fisher. (page 38)

      Gernot Frenking

      Article first published online: 2 DEC 2011 | DOI: 10.1002/anie.201106726

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      Oxford University Press, New York, 2010. 304 pp., hardcover, $ 24.95.—ISBN 978-0195393965

  12. Highlights

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    1. Organocatalysis

      1,2-Dicarbonyl Compounds as Pronucleophiles in Organocatalytic Asymmetric Transformations (pages 40–42)

      Wilfried Raimondi, Dr. Damien Bonne and Prof. Jean Rodriguez

      Article first published online: 30 NOV 2011 | DOI: 10.1002/anie.201106741

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      Organocatalysis likes them too! 1,2-dicarbonyl compounds possess high synthetic potential because of their adjacent multiple reactive centers. Recent contributions indicate that these reactive species, with an appropriate activation mode, may also act as efficient pronucleophiles in asymmetric organocatalyzed sequential or domino transformations including C[BOND]C or C[BOND]N bond formation (see scheme).

    2. Molecular Magnetism

      Chilling with Magnetic Molecules (pages 43–45)

      Prof. Dr. Roberta Sessoli

      Article first published online: 31 OCT 2011 | DOI: 10.1002/anie.201104448

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      Fridge magnets: Molecular magnetism appears to be able to provide an alternative route for low-temperature refrigeration by providing molecules with large spin and weak magnetic anisotropy that display a large magnetocaloric effect.

    3. Indole Chemistry

      Exploiting the Electrophilic Properties of Indole Intermediates: New Options in Designing Asymmetric Reactions (pages 46–48)

      Charles C. J. Loh and Prof. Dr. Dieter Enders

      Article first published online: 8 DEC 2011 | DOI: 10.1002/anie.201107575

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      Think electrophilic: While the classical π-excessive indole is well-known for its electrophilic substitutions at position C3, recent advances in asymmetric catalysis resulted in a surge in utilizing the less discussed electrophilic properties of iminium-type intermediates (see picture) in complex annulations of indoles. Advances in AuI catalysis also allow an umpolung of the classical indole C3 reactivity.

  13. Essay

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    1. History of Science

      Fritz Haber: Flawed Greatness of Person and Country (pages 50–56)

      Prof. Fritz Stern

      Article first published online: 8 DEC 2011 | DOI: 10.1002/anie.201107900

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      Onkel Fritz: In his lecture at the Centennial Celebration of The Fritz Haber Institute, Fritz Stern reflects on the strengths and flaws of the Institute′s founder. Can we judge a person without considering the historical and cultural context? In a sense, Haber's life encompassing triumph and tragedy is a reflection of his country at that time.

  14. Minireview

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    1. DNA Origami

      DNA Origami: The Art of Folding DNA (pages 58–66)

      Dr. Barbara Saccà and Prof. Dr. Christof M. Niemeyer

      Article first published online: 7 DEC 2011 | DOI: 10.1002/anie.201105846

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      Know when to fold ′em: As in the ancient art of paper folding, where a single sheet of paper is modeled into beautiful shapes, DNA origami technology allows nanoscale-addressable objects to be created from one single strand of DNA (see picture).

  15. Review

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    1. Carbon Nitride

      Polymeric Graphitic Carbon Nitride as a Heterogeneous Organocatalyst: From Photochemistry to Multipurpose Catalysis to Sustainable Chemistry (pages 68–89)

      Dr. Yong Wang, Prof. Dr. Xinchen Wang and Prof. Dr. Markus Antonietti

      Article first published online: 23 NOV 2011 | DOI: 10.1002/anie.201101182

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      Multipurpose catalyst: Graphitic carbon nitride (g-C3N4; see SEM image) is an effective (photo)catalyst for a whole series of reactions. This Review describes the synthesis of g-C3N4, how the band positions and bandgaps can be varied by copolymerization and doping and how changes in the solid-state structure can improve heterogeneous organocatalyst effectiveness.

  16. Communications

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    1. C[BOND]C Coupling

      Do Carbyne Radicals Really Exist in Aqueous Solution? (pages 90–94)

      Benny Bogoslavsky, Ophir Levy, Anna Kotlyar, Miri Salem, Dr. Faina Gelman and Prof. Dr. Avi Bino

      Article first published online: 26 OCT 2011 | DOI: 10.1002/anie.201103652

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      They do exist! Free carbyne radicals can be prepared at room temperature in an aqueous solution by the decomposition of mono- or trinuclear metal (M) complexes containing alkylidyne ligands (see scheme; red C, blue M, green H). The generated radicals then react to form a variety of organic compounds by chain-lengthening reactions in solution. They also exhibit hydrogen, oxygen, or carbon abstraction from solvent, reactant, or product molecules.

    2. Luminescent Metallomesogens

      Phosphorescent Mesomorphic Dyads Based on Tetraacetylethane Complexes of Iridium(III) (pages 95–98)

      Dr. Anton M. Prokhorov, Dr. Amedeo Santoro, Dr. J. A. Gareth Williams and Prof. Duncan W. Bruce

      Article first published online: 15 NOV 2011 | DOI: 10.1002/anie.201105212

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      A good combination: Dimeric iridium(III) luminophores with tetraacetylethane bridges led to liquid-crystalline materials with very high photoluminescence quantum yields (see picture). The same design principle allowed for the preparation of heteronuclear iridium(III)–platinum(II) dyads, which were also luminescent.

    3. Amino Acid Conformers

      Structural Dynamics of Free Amino Acids in Diffraction (pages 99–102)

      Dr. I-Ren Lee, Dr. Andreas Gahlmann and Prof. Ahmed H. Zewail

      Article first published online: 15 NOV 2011 | DOI: 10.1002/anie.201105803

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      The amino acid tryptophan exhibits complex structural changes both in the ground state, owing to multiple conformations, and upon excitation, because of the involvement of nonradiative pathways. The first report of structural dynamics using combined ultrafast electron diffraction and laser desorption methods is presented.

    4. Aromatic Stacking

      Stacked Fluoroaromatics as Supramolecular Synthons for Programming Protein Dimerization Specificity (pages 103–107)

      Christopher J. Pace, Hong Zheng, Ruben Mylvaganam, Diane Kim and Prof. Jianmin Gao

      Article first published online: 21 NOV 2011 | DOI: 10.1002/anie.201105857

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      Aromatic “bonding”: Although known to exist in proteins, aromatic stacking interactions and the energetic factors important for it are not well understood. A systematic investigation of aromatic stacking interactions in a protein model system using a series of fluorinated phenylalanine analogues illustrates the importance of dipole–dipole and dipole–induced-dipole coupling to the stability and self-sorting properties of aromatic stacking pairs.

    5. Molecular Electronics

      Solution-Processed Reduced Graphene Oxide Films as Electronic Contacts for Molecular Monolayer Junctions (pages 108–112)

      Dr. Sohyeon Seo, Misook Min, Dr. Junghyun Lee, Dr. Takhee Lee, Dr. Sung-Yool Choi and Dr. Hyoyoung Lee

      Article first published online: 11 NOV 2011 | DOI: 10.1002/anie.201105895

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      Reduction to the essential: A highly conductive and soft carbon interlayer of reduced graphene oxide (rGO) prevents the formation of a filamentary current path, achieving both high yield and true molecular effects in monolayer-based molecular devices. Junctions of the rGO interlayer contacts with molecular monolayers elucidate the molecularly resolved electronic properties of molecular resistors and nonvolatile memories.

    6. Synthetic Methods

      Gold-Catalyzed Intermolecular [4+2] and [2+2+2] Cycloadditions of Ynamides with Alkenes (pages 113–117)

      Ramesh B. Dateer, Balagopal S. Shaibu and Prof. Dr. Rai-Shung Liu

      Article first published online: 11 NOV 2011 | DOI: 10.1002/anie.201105921

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      As good as gold: Gold-catalyzed intermolecular [4+2] cycloadditions of 2-arylynamides with alkenes and gold-catalyzed [2+2+2] cycloadditions of terminal ynamides with enol ethers have been developed (see scheme). The [4+2] cycloaddition is compatible with a range of alkenes and arylynamides and the [2+2+2] cycloaddition can also accommodate a variety of different arylynamide and enol ether substrates.

    7. Fluorophosphines

      Stable Fluorophosphines: Predicted and Realized Ligands for Catalysis (pages 118–122)

      Dr. Natalie Fey, Michael Garland, Dr. Jonathan P. Hopewell, Claire L. McMullin, Dr. Sergio Mastroianni, Prof. A. Guy Orpen and Prof. Paul G. Pringle

      Article first published online: 11 NOV 2011 | DOI: 10.1002/anie.201105954

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      Ligand maps lead to treasure! The activity of complexes of fluorophosphines (R2PF) in catalytic hydroformylation and hydrocyanation is predicted from a ligand map. However, the instability of R2PF to disproportionation is well-documented. Examples of R2PF ligands (see scheme) are described that are stabilized to such an extent that they can be used in catalysis and are shown to be highly effective.

    8. NMR Spectroscopy of MOFs

      Dynamic Nuclear Polarization Enhanced Solid-State NMR Spectroscopy of Functionalized Metal–Organic Frameworks (pages 123–127)

      Dr. Aaron J. Rossini, Alexandre Zagdoun, Dr. Moreno Lelli, Dr. Jérôme Canivet, Dr. Sonia Aguado, Dr. Olivier Ouari, Prof. Paul Tordo, Dr. Melanie Rosay, Dr. Werner E. Maas, Prof. Christophe Copéret, Dr. David Farrusseng, Prof. Lyndon Emsley and Dr. Anne Lesage

      Article first published online: 15 NOV 2011 | DOI: 10.1002/anie.201106030

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      A matter of minutes: Dynamic nuclear polarization (DNP) is applied to enhance the signal of solid-state NMR spectra of metal–organic framework (MOF) materials. The signal enhancement enables the acquisition of high-quality 1D 13C solid-state NMR spectra, 2D 1H–13C dipolar HETCOR and 1D 15N solid-state NMR spectra with natural isotopic abundance in experiment times on the order of minutes. MW=microwaves.

    9. Cell Patterning

      Photocontrollable Dynamic Micropatterning of Non-adherent Mammalian Cells Using a Photocleavable Poly(ethylene glycol) Lipid (pages 128–131)

      Dr. Satoshi Yamaguchi, Shinya Yamahira, Kyoko Kikuchi, Kimio Sumaru, Toshiyuki Kanamori and Prof. Teruyuki Nagamune

      Article first published online: 21 NOV 2011 | DOI: 10.1002/anie.201106106

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      Cells in the spotlight: A substrate was coated with a poly(ethylene glycol) (PEG) segment bound to a lipid through a linker that was cleaved by UV irradiation to leave a PEG-coated area. Irradiation of an arbitrary pattern easily and rapidly yielded a high-contrast cell pattern. Only the targeted cells on the cell pattern were selectively detached without cell damage on a microfluidic device (see picture).

    10. Metastable Phase Diagrams

      A Universal Representation of the States of Chemical Matter Including Metastable Configurations in Phase Diagrams (pages 132–135)

      Prof. Dr. Martin Jansen, Dr. Ilya V. Pentin and Prof. Dr. J. Christian Schön

      Article first published online: 17 NOV 2011 | DOI: 10.1002/anie.201106220

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      Metastable matter: Traditional equilibrium phase diagrams show thermodynamic ground states of matter and thus fail to reflect the real world of chemical materials which to a large degree consists of metastable compounds. Inclusion of metastable compounds in “extended” phase diagrams is shown by determining all modifications that are locally ergodic on the relevant time and temperature scales and computing their Gibbs enthalpies (see picture).

    11. Heterogeneous Catalysis

      Design of a Silver–Cerium Dioxide Core–Shell Nanocomposite Catalyst for Chemoselective Reduction Reactions (pages 136–139)

      Dr. Takato Mitsudome, Dr. Yusuke Mikami, Motoshi Matoba, Dr. Tomoo Mizugaki, Prof. Dr. Koichiro Jitsukawa and Prof. Dr. Kiyotomi Kaneda

      Article first published online: 24 OCT 2011 | DOI: 10.1002/anie.201106244

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      Shelling out: A core–shell nanocomposite comprising an Ag nanoparticle core and a CeO2 nanoparticle shell catalyzes the chemoselective reduction of both nitrostyrenes and epoxides while retaining the C[DOUBLE BOND]C bonds (see picture). Reactions with the core–shell structures show greater chemoselectivity than conventional oxide-supported metal nanoparticles.

    12. Biological Membranes

      Electrodeposition of Single-Metal Nanoparticles on Stable Protein 1 Membranes: Application of Plasmonic Sensing by Single Nanoparticles (pages 140–144)

      Li-Xia Qin, Dr. Yang Li, Dr. Da-Wei Li, Chao Jing, Bao-Qin Chen, Wei Ma, Dr. Arnon Heyman, Prof. Oded Shoseyov, Prof. Itamar Willner, Prof. He Tian and Prof. Yi-Tao Long

      Article first published online: 21 NOV 2011 | DOI: 10.1002/anie.201106482

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      Light in the dark: Metal nanoparticles (M=Ag0, Au0, or Cu0) were electrodeposited onto ion-channel pores of a stable protein 1 membrane (see picture). The metal nanoparticles were implemented for detection of antigen–antibody binding events at the single-particle level using dark field microscopy and plasmon resonance Rayleigh scattering.

    13. Interfacial Assembly

      Nanoparticle-Stabilized Double Emulsions and Compressed Droplets (pages 145–149)

      Caroline Miesch, Irem Kosif, Dr. Eunji Lee, Dr. Jung-Keun Kim, Prof. Thomas P. Russell, Prof. Ryan C. Hayward and Prof. Todd Emrick

      Article first published online: 23 NOV 2011 | DOI: 10.1002/anie.201106665

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      Stable double emulsions, both oil-in-water-in-oil and water-in-oil-in-water, stabilized by two types of nanoparticles residing at the o/w interfaces (see picture; red: CdSe quantum dots) were prepared in a simple fashion by shaking, and with narrow size distributions by microcapillary flow focusing. These double-emulsion droplets proved stable against coalescence throughout solvent evaporation, allowing for formation of nanoparticle foams and hexagonally arrayed structures.

      Corrected by:

      Corrigendum: Corrigendum: Nanoparticle-Stabilized Double Emulsions and Compressed Droplets

      Vol. 51, Issue 16, 3740, Article first published online: 11 APR 2012

    14. Synthetic Methods

      Platinum-Catalyzed Direct Amination of Allylic Alcohols with Aqueous Ammonia: Selective Synthesis of Primary Allylamines (pages 150–154)

      Dr. Kalpataru Das, Ryozo Shibuya, Yasuhito Nakahara, Nicolas Germain, Prof. Dr. Takashi Ohshima and Prof. Dr. Kazushi Mashima

      Article first published online: 15 NOV 2011 | DOI: 10.1002/anie.201106737

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      Direct amination of unactivated allylic alcohols with aqueous ammonia was catalyzed by a Pt/phosphine complex to give the corresponding allylamines along with water as the sole by-product. Under optimized reaction conditions, primary allylamines were obtained as major products with excellent monoallylation selectivity. cod=1,5-cyclooctadiene.

    15. Luminescent Inclusion Crystals

      Guest-Responsive Fluorescence of Inclusion Crystals with π-Stacked Supramolecular Beads (pages 155–158)

      Tomoaki Hinoue, Prof. Dr. Mikiji Miyata, Dr. Ichiro Hisaki and Dr. Norimitsu Tohnai

      Article first published online: 14 NOV 2011 | DOI: 10.1002/anie.201106849

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      Luminescent jewels: Unusually shaped fluorescent supramolecular clusters assemble into one-dimensional π-stacked supramolecular beads to eventually crystallize with a wide range of solvent molecules (see picture). The included solvent molecules modulate the fluorescence colors of the inclusion crystals from blue to orange-yellow as is known for the colors of gemstones.

    16. Bimetallic Nanocrystals

      Convex Polyhedral Au@Pd Core–Shell Nanocrystals with High-Index Facets (pages 159–163)

      Dongheun Kim, Young Wook Lee, Prof. Sang Bok Lee and Prof. Sang Woo Han

      Article first published online: 18 NOV 2011 | DOI: 10.1002/anie.201106899

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      The many faces of noble metals: Through the simultaneous reduction of Au and Pd ions in the presence of octahedral Au nanocrystal (NC) seeds, hexoctahedron-like convex Au@Pd core–shell NCs, enclosed predominantly by high-index {12 5 3} facets, were synthesized under aqueous room-temperature conditions (see picture). The convex Au@Pd NCs showed much higher electrocatalytic properties toward ethanol oxidation than other types of Au@Pd NCs.

    17. Near-Infrared Fluorophores

      Bright Near-Infrared Fluorophores Based on Squaraines by Unexpected Halogen Effects (pages 164–167)

      Ulrich Mayerhöffer, Benjamin Fimmel and Prof. Dr. Frank Würthner

      Article first published online: 21 NOV 2011 | DOI: 10.1002/anie.201107176

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      A lucky chance: An unexpected halogen effect afforded novel squaraine-based bright near-infrared (NIR) fluorophores with nearly total transparency in the visible region and bright emission in the NIR region beyond 900 nm (see picture).

    18. Heme–Peroxo–Copper Adducts

      Spectroscopic Elucidation of a New Heme/Copper Dioxygen Structure Type: Implications for O⋅⋅⋅O Bond Rupture in Cytochrome c Oxidase (pages 168–172)

      Dr. Matthew T. Kieber-Emmons, Munzarin F. Qayyum, Yuqi Li, Dr. Zakaria Halime, Prof. Keith O. Hodgson, Prof. Britt Hedman, Prof. Kenneth D. Karlin and Prof. Edward I. Solomon

      Article first published online: 16 NOV 2011 | DOI: 10.1002/anie.201104080

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      All's well that ends well: The geometric and electronic structure of the first end-on heme–peroxo–copper adduct (see picture) was elucidated using UV/Vis, resonance Raman, and X-ray absorption spectroscopy and is supported by DFT calculations. Coordination of the axial base is correlated to a spin-state change, leading to enhanced biomimetic reactivity, and gives insight into O[BOND]O bond cleavage by cytochrome c oxidase.

    19. Arynes

      [16]Cloverphene: a Clover-Shaped cata-Condensed Nanographene with Sixteen Fused Benzene Rings (pages 173–177)

      Dr. José M. Alonso, Dr. Alba E. Díaz-Álvarez, Alejandro Criado, Dr. Dolores Pérez, Dr. Diego Peña and Prof. Dr. Enrique Guitián

      Article first published online: 9 NOV 2011 | DOI: 10.1002/anie.201104935

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      Living in clover: Sequential [4+2] and [2+2+2] aryne cycloadditions allow the isolation of cloverlike and archlike nanographenes (see picture). This approach led to the synthesis of the largest cata-condensed aromatic hydrocarbon that has been obtained to date, a system formed by 16 fused benzene rings (22 benzene rings in total) and 102 sp2 carbon atoms.

    20. Architecture Effects

      Facet-Mediated Photodegradation of Organic Dye over Hematite Architectures by Visible Light (pages 178–182)

      Xuemei Zhou, Jinyao Lan, Prof. Gang Liu, Prof. Ke Deng, Prof. Yanlian Yang, Prof. Guangjun Nie, Prof. Jiaguo Yu and Prof. Linjie Zhi

      Article first published online: 15 NOV 2011 | DOI: 10.1002/anie.201105028

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      Photodegradation of rhodamine B in the presence of H2O2 by visible light over α-Fe2O3 architectures has been investigated (see picture; left to right: 1D nanorods, 2D nanoplates, 3D nanocubes). A link between the exposed facets of α-Fe2O3 architectures and their photoreactivity is established, following {110}>{012}≫{001}.

    21. Synthetic Methods

      Regio- and Stereoselective Synthesis of Cyclopentenones: Intermolecular Pseudo-Pauson–Khand Cyclization (pages 183–186)

      Prof. José Barluenga, Ana Álvarez-Fernández, Dr. Ángel L. Suárez-Sobrino and Prof. Miguel Tomás

      Article first published online: 17 NOV 2011 | DOI: 10.1002/anie.201105362

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      Doing the two step: A very simple two-step access to polysubstituted cyclopentenones from terminal alkynes, [M(CO)6], and bromoalkenes is described. This protocol is an alternative to the intermolecular Pauson–Khand reaction, and can be used with a variety of bromoalkenes. Moreover, the final quenching allows the installation of reactive electrophiles (E). The enantiopure product cyclopentenones can be synthesized with an all-carbon-substituted quaternary stereocenter.

    22. CO2 Recycling

      A Diagonal Approach to Chemical Recycling of Carbon Dioxide: Organocatalytic Transformation for the Reductive Functionalization of CO2 (pages 187–190)

      Christophe Das Neves Gomes, Dr. Olivier Jacquet, Dr. Claude Villiers, Dr. Pierre Thuéry, Dr. Michel Ephritikhine and Dr. Thibault Cantat

      Article first published online: 29 SEP 2011 | DOI: 10.1002/anie.201105516

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      Lateral thinking: A diagonal approach to CO2 recycling has been explored for the formation of both functionalized and energetic chemicals featuring a reduced carbon center. The strategy relies on the tandem use of a functionalization reagent and a reductant that can be independently modified to access a wide spectrum of chemicals from CO2. It is exemplified with an organocatalytic process to convert CO2 into formamides (see picture).

    23. Peptide Synthesis

      A Synthetic Approach to a Peptide α-Thioester from an Unprotected Peptide through Cleavage and Activation of a Specific Peptide Bond by N-Acetylguanidine (pages 191–196)

      Dr. Ryo Okamoto, Keiko Morooka and Prof. Dr. Yasuhiro Kajihara

      Article first published online: 9 NOV 2011 | DOI: 10.1002/anie.201105601

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      A different route to peptide α-thioesters through a new peptide-bond-cleavage method at a cysteine residue by S-thiocarbonylation and subsequent treatment with N-acetylguanidine is described (see scheme). The resultant peptidyl-N-acetylguanidine can be converted into the corresponding peptide α-thioester and is also usable as an alternative to a peptide α-thioester. This method allows efficient kinetically controlled ligation in the presence of thiols.

    24. C[BOND]H Activation

      One-Pot Synthesis of Isoquinolinium Salts by Rhodium-Catalyzed C[BOND]H Bond Activation: Application to the Total Synthesis of Oxychelerythrine (pages 197–200)

      Jayachandran Jayakumar, Dr. Kanniyappan Parthasarathy and Prof. Dr. Chien-Hong Cheng

      Article first published online: 15 NOV 2011 | DOI: 10.1002/anie.201105755

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      It's worth its salt: The title reaction leads to the synthesis of highly substituted isoquinolinium salts (see scheme; Cp*=Me5C5). The reaction proceeds through a C[BOND]H activation and a subsequent annulation in the presence of a rhodium catalyst. The reaction mechanism is discussed as well as its application to the synthesis of the natural product oxychelerythrine.

    25. Synthetic Methods

      Chiral Iridium Catalysts Bearing Spiro Pyridine-Aminophosphine Ligands Enable Highly Efficient Asymmetric Hydrogenation of β-Aryl β-Ketoesters (pages 201–203)

      Prof. Jian-Hua Xie, Xiao-Yan Liu, Xiao-Hui Yang, Jian-Bo Xie, Prof. Li-Xin Wang and Prof. Qi-Lin Zhou

      Article first published online: 16 NOV 2011 | DOI: 10.1002/anie.201105780

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      Tons of TONs: Chiral iridium catalysts bearing ligand 1 are highly efficient for the asymmetric hydrogenation of β-substituted β-ketoesters. The product β-hydroxyesters are delivered in high yield with excellent enantioselectivities and high turnover numbers (TONs). cod= 1,5-cyclooctadiene.

    26. Ester Enolate Alkylations

      Palladium-Catalyzed Allylic Alkylation of Carboxylic Acid Derivatives: N-Acyloxazolinones as Ester Enolate Equivalents (pages 204–208)

      Prof. Barry M. Trost, Dr. David J. Michaelis, Julie Charpentier and Dr. Jiayi Xu

      Article first published online: 16 NOV 2011 | DOI: 10.1002/anie.201105801

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      Triple A: A general asymmetric allylic alkylation of ester enolate equivalents at the carboxylic acid oxidation state is reported. N-Acylbenzoxazolinone-derived enol carbonates were synthesized and employed in the palladium-catalyzed alkylation reaction. The imide products were readily converted into a series of carboxylic acid derivatives without loss of enantiopurity.

    27. Chemical Protein Synthesis

      A One-Pot Three-Segment Ligation Strategy for Protein Chemical Synthesis (pages 209–213)

      Nathalie Ollivier, Dr. Jérôme Vicogne, Aurélie Vallin, Hervé Drobecq, Rémi Desmet, Ouafâa El Mahdi, Bérénice Leclercq, Dr. Gautier Goormachtigh, Dr. Véronique Fafeur and Dr. Oleg Melnyk

      Article first published online: 16 NOV 2011 | DOI: 10.1002/anie.201105837

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      Three in one: Native chemical ligation (NCL) and bis(2-sulfanylethyl)amido (SEA) ligation allow the one-pot assembly of three peptide segments in the N-to-C direction. The SEA group (see picture, blue) is switched off by intramolecular disulfide bond formation during NCL. Then, a phosphine switches it on to trigger the second SEA ligation step. The K1 domain of the hepatocyte growth factor was synthesized and found to be biologically active.

    28. Phosphorous Heterocycles

      2,2′-Biphospholes: Building Blocks for Tuning the HOMO–LUMO Gap of π-Systems Using Covalent Bonding and Metal Coordination (pages 214–217)

      Hui Chen, Wylliam Delaunay, Liujian Yu, Dr. Damien Joly, Zuoyong Wang, Jin Li, Zisu Wang, Dr. Christophe Lescop, Denis Tondelier, Bernard Geffroy, Prof. Zheng Duan, Prof. Muriel Hissler, Prof. François Mathey and Prof. Régis Réau

      Article first published online: 14 NOV 2011 | DOI: 10.1002/anie.201105924

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      A new angle: The insertion of a 2,2′-biphosphole subunit into π-conjugated systems offers a new way to control the HOMO–LUMO gap. Tuning of the dihedral angle (θ) between the two phosphorous heterocycles, either by metal coordination or covalent bonding through the P substitution can lead to control of the band gap. These new π-conjugated systems can be used as emitting materials in white organic light-emitting devices (WOLEDs).

    29. Radical Reactions

      Cross-Coupling of Aryl Grignard Reagents with Aryl Iodides and Bromides through SRN1 Pathway (pages 218–221)

      Prof. Eiji Shirakawa, Yumi Hayashi, Ken-ichi Itoh, Ryo Watabe, Nanase Uchiyama, Wataru Konagaya, Seiji Masui and Prof. Tamio Hayashi

      Article first published online: 14 NOV 2011 | DOI: 10.1002/anie.201106086

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      Game, SET, and match: Aryl Grignard reagents undergo coupling with aryl halides when toluene is used as a solvent in combination with a small amount of tetrahydrofuran (see scheme). The reaction proceeds through an SRN1 mechanism, and does not require any transition metal catalysts.

    30. Visible-Light Photocatalysis

      Intermolecular [3+2] Cycloaddition of Cyclopropylamines with Olefins by Visible-Light Photocatalysis (pages 222–226)

      Dr. Soumitra Maity, Dr. Mingzhao Zhu, Ryan Spencer Shinabery and Prof. Dr. Nan Zheng

      Article first published online: 23 NOV 2011 | DOI: 10.1002/anie.201106162

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      It's the power of light! A visible-light-mediated intermolecular [3+2] cycloaddition of mono- and bicyclic cyclopropylamines with olefins catalyzed by [Ru(bpz)3](PF6)2⋅2 H2O has been developed to furnish aminocyclopentane derivatives in good yields (see scheme, bpz=2,2′-bipyrazine). Saturated 5,5- and 6,5-fused heterocycles are obtained in synthetically useful yields and diastereoselectivity.

    31. Homogeneous Catalysis

      Palladium-Catalyzed Decarboxylative C[BOND]H Bond Arylation of Thiophenes (pages 227–231)

      Dr. Peng Hu, Min Zhang, Xiaoming Jie and Prof. Weiping Su

      Article first published online: 15 NOV 2011 | DOI: 10.1002/anie.201106451

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      An efficient method involving a Pd/PCy3 catalyst in combination with a stoichiometric amount of Ag2CO3 has been established for the decarboxylative C[BOND]H bond arylation of thiophenes to give 2-arylthiophenes (see scheme; Cy=cyclohexyl). Electron-rich, electron-deficient, and heterocyclic benzoic acids can be used as the arylating reagent and a broad range of substituents on the thiophene are tolerated.

    32. Nitrogen Oxides

      Covalent Capture of Nitrous Oxide by N-Heterocyclic Carbenes (pages 232–234)

      Alexander G. Tskhovrebov, Dr. Euro Solari, Dr. Matthew D. Wodrich, Dr. Rosario Scopelliti and Prof. Kay Severin

      Article first published online: 16 NOV 2011 | DOI: 10.1002/anie.201106589

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      A good catch: N-Heterocyclic carbenes (NHCs) form stable adducts with nitrous oxide (N2O) under mild reaction conditions. The adducts display unique reactivity as evidenced by an alkylation reaction which leads to a rupture of the N[BOND]N bond.

    33. Borylation

      Copper-Catalyzed Borylation Reactions of Alkynes and Arynes (pages 235–238)

      Prof. Hiroto Yoshida, Shota Kawashima, Yuki Takemoto, Kengo Okada, Prof. Joji Ohshita and Prof. Ken Takaki

      Article first published online: 14 NOV 2011 | DOI: 10.1002/anie.201106706

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      One, two, three, four: A copper(I)–phosphine complex catalyzes the diborylation of alkynes and arynes, and the tri- or tetraborylation of propargyl ethers (see scheme; pin=pinacolato). In the latter cases, the C[BOND]O bond(s) as well as the C[TRIPLE BOND]C bond are borylated in one pot. Furthermore, a diborylation product serves as an intermediate in the efficient synthesis of ortho-terphenyls with pharmacological activity.

    34. Nanotechnology

      LiNi0.5Mn1.5O4 Hollow Structures as High-Performance Cathodes for Lithium-Ion Batteries (pages 239–241)

      Dr. Liang Zhou, Prof. Dongyuan Zhao and Prof. XiongWen (David) Lou

      Article first published online: 17 NOV 2011 | DOI: 10.1002/anie.201106998

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      Built to last: Uniform LiNi0.5Mn1.5O4 hollow microspheres and microcubes (see picture; scale bars: 1 μm) with nanosized building blocks have been synthesized by a facile impregnation method followed by a simple solid-state reaction. The resultant LiNi0.5Mn1.5O4 hollow structures deliver a discharge capacity of about 120 mA h g−1 over prolonged cycling and exhibit excellent rate capability.

    35. Supramolecular Interactions

      Selective Host–Guest Binding of Anions without Auxiliary Hydrogen Bonds: Entropy as an Aid to Design (pages 242–246)

      Andrei Ursu and Prof. Franz P. Schmidtchen

      Article first published online: 18 NOV 2011 | DOI: 10.1002/anie.201106018

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      Entropy matters! In contrast to classic host–guest design, which employs dedicated enthalpic interactions of the binding partners, the novel electroneutral host 1 binds its anionic guests by virtue of an overwhelmingly positive entropy of association. The prime driving force is guest desolvation. Despite the total omission of hydrogen bonding, host 1 is one of the best electroneutral receptors known for binding anions in polar solution.

    36. 20S Proteasome Inhibitors

      Hydroxyureas as Noncovalent Proteasome Inhibitors (pages 247–249)

      M. Chem. Nerea Gallastegui, M. Sc. Philipp Beck, M. Sc. Marcelino Arciniega, Prof. Dr. Robert Huber, Stefan Hillebrand and Prof. Dr. Michael Groll

      Article first published online: 21 NOV 2011 | DOI: 10.1002/anie.201106010

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      Inhibitors with a new mechanism of action are needed for 20S proteasome (CP) inhibition owing to the ineffectiveness of current market drugs against some types of solid tumors. A novel class of nonpeptidic CP inhibitors has been developed, which display reversible and noncovalent binding. The structure-based design of these highly active and site-specific inhibitors revealed unexplored binding subpockets.

    37. DNA Folding

      Time-Resolved NMR Spectroscopic Studies of DNA i-Motif Folding Reveal Kinetic Partitioning (pages 250–253)

      Dipl.-Chem. Anna Lena Lieblein, Dr. Janina Buck, Dr. Kai Schlepckow, Dr. Boris Fürtig and Prof. Dr. Harald Schwalbe

      Article first published online: 17 NOV 2011 | DOI: 10.1002/anie.201104938

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      Get the zipper right: Time-resolved NMR spectroscopy measurements reveal kinetic partitioning for pH-induced DNA i-motif formation (see scheme). The data characterize the folding pathway of i-motifs and provide a biophysical based description of pH-dependent folding processes as utilized in live-cell pH sensors.

    38. DNA Modification

      Barcoded Nucleotides (pages 254–257)

      Dr. Anna Baccaro, Dipl.-Chem. Anna-Lena Steck and Prof. Dr. Andreas Marx

      Article first published online: 14 NOV 2011 | DOI: 10.1002/anie.201105717

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      Designer labels: DNA polymerases are able to incorporate oligodeoxynucleotide(ODN)-modified nucleotides that are 40-times bigger than the natural substrate. The result is bio-barcoded DNA (see scheme). Incorporation of an ODN-modified nucleotide can be detected in solution and on solid support by hybridization of a fluorescent-dye-labeled DNA strand complementary to the ODN.

    39. Computer-Assisted Drug Screening

      Immunosuppressive Small Molecule Discovered by Structure-Based Virtual Screening for Inhibitors of Protein–Protein Interactions (pages 258–261)

      Tim Geppert, Stefanie Bauer, Dr. Jan A. Hiss, Elea Conrad, Michael Reutlinger, Dr. Petra Schneider, Dr. Martin Weisel, Bernhard Pfeiffer, Prof. Dr. Karl-Heinz Altmann, Priv.-Doz. Dr. Zoe Waibler and Prof. Dr. Gisbert Schneider

      Article first published online: 16 NOV 2011 | DOI: 10.1002/anie.201105901

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      Interfering with interferon: A low-molecular-weight inhibitor has been discovered that blocks the interaction between interferon-α (IFN-α) and its receptor (see picture for a model of the interfaces). The resulting lead compound significantly reduces IFN-α production in vitro. NMR and SPR experiments confirm the direct interaction of the inhibitor with IFN-α.

    40. Redox-Active Cavitands

      Quinone-Based, Redox-Active Resorcin[4]arene Cavitands (pages 262–266)

      Igor Pochorovski, Prof. Dr. Corinne Boudon, Dr. Jean-Paul Gisselbrecht, Dr. Marc-Olivier Ebert, Dr. W. Bernd Schweizer and Prof. Dr. François Diederich

      Article first published online: 14 NOV 2011 | DOI: 10.1002/anie.201106031

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      Catch it if you can! Redox-active resorcin[4]arene cavitands with quinone walls can be reversibly reduced to the hydroquinone form, influencing their host–guest complexation strength. Specifically, a top-covered triptycenequinone cavitand forms kinetically stable complexes with cycloalkanes; this complexation is weaker in the reduced hydroquinone form.

    41. Plasmid DNA Topoisomers

      Topology-Selective Chromatography Reveals Plasmid Supercoiling Shifts during Fermentation and Allows Rapid and Efficient Preparation of Topoisomers (pages 267–270)

      Dr. Marek Mahut, Mag. Elisabeth Haller, Mag. Parisa Ghazidezfuli, Dipl.-Ing. Michael Leitner, Dr. Andreas Ebner, Prof. Peter Hinterdorfer, Prof. Wolfgang Lindner and Prof. Michael Lämmerhofer

      Article first published online: 16 NOV 2011 | DOI: 10.1002/anie.201106495

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      Recognizing pDNA supercoils: Differently supercoiled species of the same plasmid DNA can be separated by topology-selective chromatography. Two-dimensional HPLC proved that the supercoiling changes during fermentation. Thus, a new quality criterium might help to optimize the effectivity of future genetic drugs and vaccines.

  17. And Finally

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    1. Web Applications

      CatApp: A Web Application for Surface Chemistry and Heterogeneous Catalysis (pages 272–274)

      Dr. Jens S. Hummelshøj, Dr. Frank Abild-Pedersen, Dr. Felix Studt, Dr. Thomas Bligaard and Prof. Jens K. Nørskov

      Article first published online: 12 DEC 2011 | DOI: 10.1002/anie.201107947

      Thumbnail image of graphical abstract

      A rich source: Calculated reaction and activation energies for elementary coupling reactions occurring on metal surfaces can be found by using a web application. This tool provides access to data for reactions of molecules with up to three C, N, or O atoms on a number of different transition-metal surfaces. The underlying dataset is generated from a consistent set of DFT calculations and extrapolations based on linear scaling relations.

  18. Preview

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Inside Back Cover
    5. Back Cover
    6. Editorial
    7. Graphical Abstract
    8. Flashback
    9. News
    10. Author Profile
    11. News
    12. Book Review
    13. Highlights
    14. Essay
    15. Minireview
    16. Review
    17. Communications
    18. And Finally
    19. Preview
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      Preview: Angew. Chem. Int. Ed. 2/2012 (page 276)

      Article first published online: 29 DEC 2011 | DOI: 10.1002/anie.201190112

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