Angewandte Chemie International Edition

Cover image for Vol. 46 Issue 1‐2

December 18, 2006

Volume 46, Issue 1-2

Pages 1–307

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Book Review
    8. Essays
    9. Editorial
    10. Review
    11. Communications
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    1. Cover Picture: Inclusion of Cavitands and Calix[4]arenes into a Metallobridged para-(1H-Imidazo[4,5-f][3,8]phenanthrolin-2-yl)-Expanded Calix[4]arene (Angew. Chem. Int. Ed. 1-2/2007) (page 1)

      Enrique Botana, Eric Da Silva, Jordi Benet-Buchholz, Pablo Ballester and Javier de Mendoza

      Article first published online: 12 DEC 2006 | DOI: 10.1002/anie.200690172

      Hunter and hunted is not only a principle of nature but is also found in host–guest systems. J. de Mendoza and co-workers describe in their Communication on page 198 ff. how a host molecule (a small calix[4]arene or cavitand) can itself become the “prey” for a larger host (a metallocavitand made from a calix[4]arene with [3,8]phenanthroline subunits linked through Re atoms). The cover picture shows the complexation of a cavitand (by P. Ballester) superimposed on an underwater picture at Cap Andritxol, Mallorca (by E. Botana).

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Book Review
    8. Essays
    9. Editorial
    10. Review
    11. Communications
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    1. Inside Cover: A Molecular Solomon Link (Angew. Chem. Int. Ed. 1-2/2007) (page 2)

      Cari D. Pentecost, Kelly S. Chichak, Andrea J. Peters, Gareth W. V. Cave, Stuart J. Cantrill and J. Fraser Stoddart

      Article first published online: 11 JAN 2007 | DOI: 10.1002/anie.200790005

      A molecular Solomon knot was isolated from a dynamic library of molecular knots by kinetically controlled crystallization. By incorporating mixed-metal templates into the usual protocol employed in the synthesis of Borromean Rings, J. F. Stoddart and co-workers obtained a molecular Solomon link as the only crystalline product under the reaction conditions described and were able to determine its X-ray crystal structure, as they report in their Communication on page 218 ff.

  3. Editorial

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    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Book Review
    8. Essays
    9. Editorial
    10. Review
    11. Communications
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  4. Graphical Abstract

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    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Book Review
    8. Essays
    9. Editorial
    10. Review
    11. Communications
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  5. News

    1. Top of page
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    4. Editorial
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    6. News
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  6. Book Review

    1. Top of page
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  7. Essays

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    1. 1807: Observations Regarding Chemistry in the Anglo-Saxon World during the Napoleonic Period (pages 24–51)

      Otto Krätz and Elisabeth Vaupel

      Article first published online: 12 DEC 2006 | DOI: 10.1002/anie.200602455

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      Far-reaching influence: How did the cultural atmosphere in the Anglo-Saxon world shape the sciences and in particular chemistry at the beginning of the 19th century? Who were the most important figures, and what role did they play in academia as well as in the public? Impressions regarding these themes are given in this Essay.

    2. The Future of Energy Supply: Challenges and Opportunities (pages 52–66)

      Nicola Armaroli and Vincenzo Balzani

      Article first published online: 14 NOV 2006 | DOI: 10.1002/anie.200602373

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      Energy for everybody? The ever increasing world energy demand cannot be satisfied much longer with fossil fuels; alternatives are required to limit the chance of a climate collapse and the spreading of wars for natural resources. The 21st century will be largely defined by the way we face and resolve the energy crisis. This is an intricate and fascinating scientific challenge, in which chemistry will play a fundamental role, and also an unprecedented opportunity to shape a more peaceful world.

  8. Editorial

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      40 Years of Supramolecular Chemistry (pages 68–69)

      François Diederich

      Article first published online: 12 DEC 2006 | DOI: 10.1002/anie.200602704

  9. Review

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    1. Synthetic Molecular Motors and Mechanical Machines (pages 72–191)

      Euan R. Kay, David A. Leigh and Francesco Zerbetto

      Article first published online: 29 NOV 2006 | DOI: 10.1002/anie.200504313

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      Exercising demons: Although the notion of synthetic molecular-level motors and machines has been around for 150 years (for example, Maxwell's demon, see picture), it is only recently that research in this area has flourished. The current state of the art in regard to how the components of molecular-level structures can be switched, rotated, speeded up, slowed down, and directionally driven in response to stimuli is described in the Review.

  10. Communications

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    1. Hydrogen-Bonded Helical Organic Nanotubes (pages 194–197)

      G. Dan Pantoş, Paolo Pengo and Jeremy K. M. Sanders

      Article first published online: 7 NOV 2006 | DOI: 10.1002/anie.200603348

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      Twist your tubes: The self-assembly of small organic molecules is an entirely new approach to the synthesis of nanotubular structures possessing helical chirality. Amino acid derivatives of naphthalenediimide form such assemblies both in solution and in the solid state. The chirality of the nanotubes is determined by the constituent amino acid but is independent of the nature of the side chains.

      Corrected by:

      Corrigendum: Hydrogen-Bonded Helical Organic Nanotubes

      Vol. 46, Issue 13, 2138, Article first published online: 9 MAR 2007

    2. Inclusion of Cavitands and Calix[4]arenes into a Metallobridged para-(1H-Imidazo[4,5-f][3,8]phenanthrolin-2-yl)-Expanded Calix[4]arene (pages 198–201)

      Enrique Botana, Eric Da Silva, Jordi Benet-Buchholz, Pablo Ballester and Javier de Mendoza

      Article first published online: 18 OCT 2006 | DOI: 10.1002/anie.200603180

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      A hunter hunted! A highly preorganized, deep metallocavitand of nanoscale dimensions containing rhenium atoms at the four corners can be readily synthesized from a simple formyl-substituted calix[4]arene and 3,8-phenanthroquinone. Unsubstituted calix[4]arenes and cavitands without substituents on the lower rim are the ideal guests for such an expanded calixarene (see picture), and are included with binding constants of 103–105M−1.

    3. Selective Binding and Easy Separation of C70 by Nanoscale Self-Assembled Capsules (pages 202–205)

      Elisa Huerta, Gerald A. Metselaar, Alex Fragoso, Eva Santos, Carles Bo and Javier de Mendoza

      Article first published online: 10 OCT 2006 | DOI: 10.1002/anie.200603223

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      All wrapped up: An easy, highly selective separation of C70 and the higher fullerenes has been achieved by solid–liquid extraction with a 2-ureido-4-[1H]-pyrimidinone-based scaffold which wraps around the guest as a dimeric capsule (see picture), thereby solubilizing it in THF. Acidification disrupts the hydrogen-bonding network and allows easy recovery of the guest and recycling of the receptor without chromatography or tedious procedures.

    4. Electrostatic Self-Assembly of Polystyrene Microspheres by Using Chemically Directed Contact Electrification (pages 206–209)

      Logan S. McCarty, Adam Winkleman and George M. Whitesides

      Article first published online: 30 NOV 2006 | DOI: 10.1002/anie.200602914

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      Stick with me: Electrostatic charges can be induced in functionalized polystyrene beads. Oppositely charged beads then aggregate to form superstructures. A coat of small beads can self-assemble around a large bead (see optical microscopy image). After annealing, another layer of beads can be added. The technique, based on contact electrification, avoids the use of expensive equipment and enables the use of large quantities of material.

    5. Cucurbit[7]uril: A Simple Macrocyclic, pH-Triggered Hydrogelator Exhibiting Guest-Induced Stimuli-Responsive Behavior (pages 210–213)

      Ilha Hwang, Woo Sung Jeon, Hee-Joon Kim, Dongwoo Kim, Hyunuk Kim, Narayanan Selvapalam, Norifumi Fujita, Seiji Shinkai and Kimoon Kim

      Article first published online: 9 NOV 2006 | DOI: 10.1002/anie.200603149

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      Without modification of its periphery, cucurbit[7]uril (a macrocyclic cavitand comprising seven glycoluril units) forms a hydrogel. The gelation is thermoreversible and sensitive to pH, but is inhibited by the presence of alkali-metal ions and shows guest-induced stimuli-responsive behavior: upon addition of a small amount of a guest, it undergoes a reversible gel–sol transition with alternating UV irradiation and heat treatment (see picture).

    6. Proteomorphous Objects from Abiotic Backbones (pages 214–217)

      Nicolas Delsuc, Jean-Michel Léger, Stéphane Massip and Ivan Huc

      Article first published online: 19 OCT 2006 | DOI: 10.1002/anie.200603390

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      Big is beautiful: A folded synthetic molecule with a conformation that compares in size with the tertiary folds of a small protein and yet only consist of non-natural units is described. By not controlling the helical handedness allows the effect of tertiary interactions between helical modules through helix–helix side-by-side induction of handedness to be observed.

    7. A Molecular Solomon Link (pages 218–222)

      Cari D. Pentecost, Kelly S. Chichak, Andrea J. Peters, Gareth W. V. Cave, Stuart J. Cantrill and J. Fraser Stoddart

      Article first published online: 17 NOV 2006 | DOI: 10.1002/anie.200603521

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      Knots galore: With a judicious choice of ions and solvents, it is possible to amplify a molecular Solomon link by kinetically controlled crystallization from a dynamic combinatorial library of molecular knots (see scheme).

    8. Protein Recognition and Denaturation by Self-Assembling Fragments on a DNA Quadruplex Scaffold (pages 223–225)

      Debarati M. Tagore, K. Ingrid Sprinz, Steven Fletcher, Janarthanan Jayawickramarajah and Andrew D. Hamilton

      Article first published online: 30 NOV 2006 | DOI: 10.1002/anie.200603479

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      Recognize this face? Quadruplex DNA has been used as a noncovalent scaffold to project binding groups for protein recognition and denaturation, with the best quadruplex decreasing the melting temperature of cytochrome c by about 45 K.

    9. Functional Architecture of HCV IRES Domain II Stabilized by Divalent Metal Ions in the Crystal and in Solution (pages 226–229)

      Sergey M. Dibrov, Hillary Johnston-Cox, Yi-Hsin Weng and Thomas Hermann

      Article first published online: 28 NOV 2006 | DOI: 10.1002/anie.200603807

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      Around the bend: A right-angled bend in the RNA of the hepatitis C virus is stabilized by a core of divalent metal ions (shown as green and violet spheres). Crystal-structure analysis and fluorescence labeling have been used to investigate the structure and metal-ion-dependent stabilization of the RNA domain that plays a key role in viral protein synthesis.

    10. Self-Assembly of Tripodal Squaraines: Cation-Assisted Expression of Molecular Chirality and Change from Spherical to Helical Morphology (pages 230–233)

      Ayyappanpillai Ajayaghosh, Parayalil Chithra and Reji Varghese

      Article first published online: 14 NOV 2006 | DOI: 10.1002/anie.200603611

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      Let's do the twist: Tripodal squaraines self-assemble from acetonitrile to form hollow spheres, the complexation of which with Ca2+ or Mg2+ results in extended networks. An analogous chiral dye exhibits a bisignate CD couplet and a helical morphology upon Ca2+ binding (see figure). Thus, the molecular chirality of a functional dye is expressed through specific cation binding and manifested in the form of supramolecular helicity.

    11. Comparison of Thermosensitive Properties of Poly(amidoamine) Dendrimers with Peripheral N-Isopropylamide Groups and Linear Polymers with the Same Groups (pages 234–237)

      Yasuhiro Haba, Chie Kojima, Atsushi Harada and Kenji Kono

      Article first published online: 24 NOV 2006 | DOI: 10.1002/anie.200603346

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      The sensitive type: A lower critical solution temperature (LCST) is observed for dendrimers with N-isopropylamide (NIPAM) groups at all chain terminals and for poly(N-isopropylacrylamide) (PNIPAAm; see picture). A much smaller endothermic peak occurs around the LCST for NIPAM-terminated dendrimers. The globular structure of the dendrimers may cause inefficient hydration and dehydration around NIPAM groups below and above the LCST, respectively.

    12. Supramolecular Conducting Nanowires from Organogels (pages 238–241)

      Josep Puigmartí-Luis, Vladimir Laukhin, Ángel Pérez del Pino, José Vidal-Gancedo, Concepció Rovira, Elena Laukhina and David B. Amabilino

      Article first published online: 17 OCT 2006 | DOI: 10.1002/anie.200602483

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      Doped and wired: The organization of the π functional units in amide-functionalized tetrathiafulvalene in a gel by hydrogen-bonding interactions has given rise to nanofibers. Doping with iodine generates a conducting material, which upon annealing gives rise to nanowires with metal-like conductivity (see current-sensing AFM image).

    13. Assembly of Hybrid Synthetic Capsules (pages 242–244)

      Dariush Ajami, Michael P. Schramm, Alessandro Volonterio and Julius Rebek Jr.

      Article first published online: 5 DEC 2006 | DOI: 10.1002/anie.200603421

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      Different, yet compatible: A hybrid capsule is formed through hydrogen bonding between two different subunits, each of which is capable of self-assembly into homodimeric capsules. The hybrid forms in response to a guest that fills its space properly. Formation of the molecular capsule (see picture) is supported by 1H NMR spectroscopy experiments.

    14. Molecular Tectonics on Surfaces: Bottom-Up Fabrication of 1D Coordination Networks That Form 1D and 2D Arrays on Graphite (pages 245–249)

      Mathieu Surin, Paolo Samorì, Abdelaziz Jouaiti, Nathalie Kyritsakas and Mir Wais Hosseini

      Article first published online: 30 NOV 2006 | DOI: 10.1002/anie.200603558

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      Nanopatterning of multifunctional architectures, that is, 1D or 2D arrays on surfaces, can be achieved through bottom-up fabrication of 1D coordination networks by self-assembly processes. A coordinating tecton bearing both monodentate and tridentate coordination poles is combined with suitable metal centers (see scanning tunneling microscopy image).

    15. Controlled Stacking of 10 Transition-Metal Ions inside a DNA Duplex (pages 250–253)

      Guido H. Clever and Thomas Carell

      Article first published online: 30 NOV 2006 | DOI: 10.1002/anie.200603099

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      A helical turn full of metal ions! The metal–salen base-pair concept allows the incorporation of up to 10 transition-metal ions into double strands of DNA (see picture; Mn gray spheres, C gray, N blue, P orange, O red). The crosslinking provided by the metal–salen complexes conveys a high stability to the self-assembled systems.

    16. Spontaneous Knotting—From Oligoamide Threads to Trefoil Knots (pages 254–259)

      Jens Brüggemann, Stephan Bitter, Sonja Müller, Walter M. Müller, Ute Müller, Norbert M. Maier, Wolfgang Lindner and Fritz Vögtle

      Article first published online: 10 OCT 2006 | DOI: 10.1002/anie.200601938

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      Tying up loose ends: Oligoamide thread molecules can spontaneously transform into open knots, whose terminal functional groups can subsequently be chemically linked to form closed, cyclic knots (see scheme; left: threads; middle: open knots; right: molecular knots; X=N, C).

    17. Container Molecules with Portals: Reversibly Switchable Cycloalkane Complexation (pages 260–264)

      Thomas Gottschalk, Bernhard Jaun and François Diederich

      Article first published online: 30 NOV 2006 | DOI: 10.1002/anie.200603366

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      A molecular basket (see picture) and a molecular tube can be reversibly switched between closed and open forms. In their closed forms, these novel container molecules encapsulate cycloalkanes such as cyclohexane. Their binding capabilities can be completely turned off by the addition of acid. Neutralization with base leads to restoration of the original complexes.

    18. Threading Cesium Ions: Metal, Host, and Ligand Control in Supramolecular Coordination Chemistry (pages 265–268)

      Rolf W. Saalfrank, Andreas Scheurer, Ralph Puchta, Frank Hampel, Harald Maid and Frank W. Heinemann

      Article first published online: 28 NOV 2006 | DOI: 10.1002/anie.200603203

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      Threads of cesium ions can be generated through supramolecular coordination chemistry in a one-pot synthesis. The cesium ions are threaded together, like in a pearl necklace, with surprisingly short interatomic distances. The figure shows the space-filling model of the dicationic repeating unit of the 1D coordination polymer (left) and the cesium threads alone in the unit cell (right). C black, Cs green, Cu yellow, O red, N blue.

    19. Origin of Spectral Tuning in Rhodopsin—It Is Not the Binding Pocket (pages 269–271)

      Sivakumar Sekharan, Minoru Sugihara and Volker Buss

      Article first published online: 22 NOV 2006 | DOI: 10.1002/anie.200603306

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      The counterion, not the binding pocket, shifts the absorption of the protonated Schiff base of 11-cis-retinal into the visible region. This conclusion was drawn from high-level CASPT2 calculations on the visual pigment rhodopsin (the optimized structure of the binding pocket is shown).

    20. Porous Cobalt(II)–Organic Frameworks with Corrugated Walls: Structurally Robust Gas-Sorption Materials (pages 272–275)

      Simon M. Humphrey, Jong-San Chang, Sung Hwa Jhung, Ji Woong Yoon and Paul T. Wood

      Article first published online: 28 NOV 2006 | DOI: 10.1002/anie.200601627

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      Resilient hosts: The porous coordination solids CUK-1 (see structure; Co purple, C gray, N blue, O red/pink) and CUK-2 are synthesized from unsymmetrical ligands and CoII ions. Even after the removal of co-crystallized guests, the host frameworks are exceptionally stable. CUK-1 shows a high capacity for H2 adsorption and is one of very few materials capable of separating N2 from O2.

    21. A Computational Method To Characterize Framework Aluminum in Aluminosilicates (pages 276–278)

      Elena García-Pérez, David Dubbeldam, Bei Liu, Berend Smit and Sofía Calero

      Article first published online: 10 NOV 2006 | DOI: 10.1002/anie.200603136

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      Aluminum sites in zeolites are difficult to locate experimentally, and hence an indirect theoretical approach is proposed that identifies the most likely positions of the aluminum atoms by matching simulation results with available experimental data. The picture shows a model unit cell of FER-type zeolite with the four distinct T-sites for aluminum in green.

    22. Gold(I)-Catalyzed Bis-Spiroketalization: Synthesis of the Trioxadispiroketal-Containing A–D Rings of Azaspiracid (pages 279–282)

      Yongfeng Li, Feng Zhou and Craig J. Forsyth

      Article first published online: 4 DEC 2006 | DOI: 10.1002/anie.200601963

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      Au-dacious ring synthesis: An efficient synthesis of the A–D rings of azaspiracid has been developed by using a Co-catalyzed oxaetherification to form the fused 2,5-trans-configured trisubstituted tetrahydrofuran D ring, and an unprecedented Au-catalyzed bis-spiroketal formation wherein a bridging alkyne served as a surrogate for the C10 ketal (see scheme; PMB=para-methoxybenzyl, TBDPS=tert-butyldiphenylsilyl).

    23. Gold(I)-Catalyzed Intramolecular Enantioselective Hydroalkoxylation of Allenes (pages 283–285)

      Zhibin Zhang and Ross A. Widenhoefer

      Article first published online: 12 DEC 2006 | DOI: 10.1002/anie.200603260

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      Turned by gold: The gold(I)-catalyzed enantioselective hydroalkoxylation of allenes proceeded rapidly to give useful oxygen heterocycles in high yields and with high stereoselectivity. The procedure was also effective for the cyclization of γ-hydroxyallenes that possess an axially chiral allenyl moiety and for the cyclization of δ-hydroxyallenes.

    24. Computer-Aided Rational Design of Catalytic Antibodies: The 1F7 Case (pages 286–290)

      S. Martí, J. Andrés, E. Silla, V. Moliner, I. Tuñón and J. Bertrán

      Article first published online: 24 NOV 2006 | DOI: 10.1002/anie.200603293

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      Thinking it through: Details of the transition-state structures of the chorismate to prephenate rearrangement in the active site of the 1F7 (N33S) mutant were obtained by computer-aided rational design. This method may be used to determine whether antibody scaffolds are evolutionary dead ends or if they can be further improved.

    25. Local Atomic Order and Infrared Spectra of Biogenic Calcite (pages 291–294)

      Rachel Gueta, Amir Natan, Lia Addadi, Steve Weiner, Keith Refson and Leeor Kronik

      Article first published online: 24 NOV 2006 | DOI: 10.1002/anie.200603327

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      Shining light on local order: The relations between local crystalline order and peak intensities in the infrared spectra of calcite are explained in terms of different sensitivities to Ca[BOND]O and O⋅⋅⋅O distances (see picture) by comparing ab initio phonon spectra for ideal and distorted calcite unit cells with experimental spectra of various biogenic and geological calcites.

    26. An Aqueous Rechargeable Lithium Battery with Good Cycling Performance (pages 295–297)

      Gaojun Wang, Lijun Fu, Nahong Zhao, Lichun Yang, Yuping Wu and Haoqing Wu

      Article first published online: 28 NOV 2006 | DOI: 10.1002/anie.200603699

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      “Green” batteries: The cycling of an aqueous rechargeable lithium battery (ARLB) with an output voltage of 1.05 V is markedly improved by choosing the appropriate intercalation compounds as electrode materials (see diagram). This system is, in principle, very stable and provides a means to explore new energy-storage and conversion systems, especially for use in future electric vehicles.

    27. A General Method for the Preparation of Ethers Using Water-Resistant Solid Lewis Acids (pages 298–300)

      Avelino Corma and Michael Renz

      Article first published online: 30 NOV 2006 | DOI: 10.1002/anie.200604018

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      This most ethereal of cascades: Water-resistant single isolated Lewis acids within the framework of molecular sieves act as excellent general catalysts for the synthesis of ethers (see scheme). On this basis, an environmentally friendly process has been developed for the preparation of fine chemicals that involves a one-pot Meerwein–Ponndorf–Verley reduction/etherification cascade.

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    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Book Review
    8. Essays
    9. Editorial
    10. Review
    11. Communications
    12. Preview
    1. Preview: Angew. Chem. Int. Ed. 3/2007 (page 307)

      Article first published online: 12 DEC 2006 | DOI: 10.1002/anie.200690174

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