ChemistryOpen

Cover image for Vol. 6 Issue 2

Early View (Online Version of Record published before inclusion in an issue)

Editors: Karen Hindson, Haymo Ross; Deputy Editor: Kate Lawrence

Impact Factor: 3.585

ISI Journal Citation Reports © Ranking: 2015: 43/163 (Chemistry Multidisciplinary)

Online ISSN: 2191-1363

Associated Title(s): Angewandte Chemie International Edition, Chemistry - A European Journal, Chemistry – An Asian Journal

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  1. Communications

    1. You have full text access to this OnlineOpen article
      The Hidden Face of Wine Polyphenol Polymerization Highlighted by High-Resolution Mass Spectrometry

      Dr. Anna Vallverdú-Queralt, Emmanuelle Meudec, Matthias Eder, Dr. Rosa M. Lamuela-Raventos, Dr. Nicolas Sommerer and Dr. Véronique Cheynier

      Version of Record online: 15 MAY 2017 | DOI: 10.1002/open.201700044

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      Two plus one makes an infinity: Non-targeted strategies based on high-resolution mass spectrometry and Kendrick mass defect plots demonstrate that random cascade reactions in a simple wine-like model system consisting of anthocyanins, epicatechin, and acetaldehyde generate high complexity. Wine composition likely results from similar step growth condensation and polymerization reactions involving additional building blocks and reactions

    2. You have full text access to this OnlineOpen article
      Reductive Deamination by Benzyne for Deoxy Sugar Synthesis Through a Domino Reaction

      Prof. Jih Ru Hwu, D. Balaji Chandrasekhar, Kuo Chu Hwang, Chun-Cheng Lin, Jia-Cherng Horng and Fa-Kuen Shieh

      Version of Record online: 5 MAY 2017 | DOI: 10.1002/open.201700050

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      Sweet talk: As an oxidized form of benzene, benzyne can act as a reducing agent to remove the nitrogen and sulfur atoms from 1,3-thiazolidine-2-thiones. This “reagent” is applied in the synthesis of deoxy sugars from amino sugars and ketoses.

  2. Full Papers

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      Sequential Uncaging with Green Light can be Achieved by Fine-Tuning the Structure of a Dicyanocoumarin Chromophore

      Albert Gandioso, Marta Palau, Alba Nin-Hill, Ivanna Melnyk, Dr. Carme Rovira, Dr. Santi Nonell, Dr. Dolores Velasco, Dr. Jaume García-Amorós and Dr. Vicente Marchán

      Version of Record online: 5 MAY 2017 | DOI: 10.1002/open.201700067

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      Lighting the way: Photolysis studies with a series of dicyanocoumarin-based photocages of carboxylic acids and amines have shown that both the structure of the coumarin chromophore, the nature of the leaving group, and the type of bond to be photocleaved (ester or carbamate) strongly influence the rate and efficiency of the uncaging process upon green-light irradiation.

    2. You have full text access to this OnlineOpen article
      Synthetic Approaches for the Preparation of Phosphoramidate Prodrugs of 2′-Deoxypseudoisocytidine

      Dr. Michaela Serpi, Roberto De Biasi, Dr. Fabrizio Pertusati, Dr. Magdalena Slusarczyk and Prof. Christopher McGuigan

      Version of Record online: 5 MAY 2017 | DOI: 10.1002/open.201700019

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      C the difference: 2′-Deoxypseudoisocytidine is a C-nucleoside with antileukemic activity. A series of phosphoramidate prodrugs of this C-nucleoside were synthesized. Their synthesis proved challenging due to unexpected side reactions (double phosphorylation and epimerization). Their enzymatic activation was found to be similar to that of N-linked nucleoside ProTides.

  3. Communications

    1. You have full text access to this OnlineOpen article
      Peroxidase Activity of a c-Type Cytochrome b5 in the Non-Native State is Comparable to that of Native Peroxidases

      Shan Hu, Bo He, Dr. Ke-Jie Du, Xiao-Juan Wang, Shu-Qin Gao and Prof. Dr. Ying-Wu Lin

      Version of Record online: 2 MAY 2017 | DOI: 10.1002/open.201700055

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      Non-native is active: A c-type cytochome b5, with heme covalently linked to the protein matrix, exhibits impressive peroxidase activity in the guanidine hydrochloride (GdnHCl)-induced non-native state, which is comparable to that of native peroxidases and presents an alternative approach to the design of functional artificial metalloenzymes.

  4. Full Papers

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      Electronic π-to-π* Excitations of Rhodamine Dyes Exhibit a Time-Dependent Kohn–Sham Theory “Cyanine Problem”

      Dr. Barry Moore II, Robert L. Schrader, Dr. Karol Kowalski and Prof. Jochen Autschbach

      Version of Record online: 2 MAY 2017 | DOI: 10.1002/open.201700046

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      Overestimated energies for dyes: Time-dependent density functional theory overestimates the energies of the longest-wavelength π-to-π* transition of a series of rhodamine-type dyes. Issues similar to those long known for cyanine dyes are identified, and diagnostics for these issues are suggested.

    2. You have full text access to this OnlineOpen article
      Deeper Insight into the Six-Step Domino Reaction of Aldehydes with Malononitrile and Evaluation of Antiviral and Antimalarial Activities of the Obtained Bicyclic Products

      Christina M. Bock, Dr. Gangajji Parameshwarappa, Simon Bönisch, Prof. Dr. Walter Bauer, Dr. Corina Hutterer, Maria Leidenberger, Prof. Dr. Oliver Friedrich, Prof. Dr. Manfred Marschall, Prof. Dr. Barbara Kappes, Prof. Dr. Andreas Görling and Prof. Dr. Svetlana B. Tsogoeva

      Version of Record online: 26 APR 2017 | DOI: 10.1002/open.201700005

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      The domino effect: Investigations of the metal-free six-step domino reaction of aldehydes with malononitrile are reported, extending the scope of aldehydes and organocatalysts. NMR studies of selected products and DFT calculations of the thermodynamics of this reaction are presented. Evaluation of seven highly functionalized and artemisinin-containing domino products against human cytomegalovirus and Plasmodium falciparum 3D7 reveals high activity, with the compounds outperforming the clinical drugs ganciclovir and chloroquine.

  5. Communications

    1. You have full text access to this OnlineOpen article
      (BEDT-TTF)2Cu2(HCOO)5: An Organic–Inorganic Hybrid Conducting Magnet

      Prof. Bin Zhang, Dr. Yan Zhang, Prof. Zheming Wang, Prof. Zengqiang Gao, Prof. Deliang Yang, Prof. Dongwei Wang, Yanjun Guo and Daoben Zhu

      Version of Record online: 19 APR 2017 | DOI: 10.1002/open.201700041

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      Code of conduct: An organic–inorganic hybrid (BEDT-TTF)2Cu2 (HCOO)5 composed of a θ-BEDT-TTF+05 layer and square lattice anionic sheet [Cu2(HCOO)5-]n is synthesized. The crystal shows long-range magnetic ordering at 8.0 K and is semiconducting with σrt=0.1 S cm. Thus, an antiferromagnetic square lattice is introduced into a molecular crystal.

  6. Full Papers

    1. You have full text access to this OnlineOpen article
      Tin, Bismuth, and Tin–Bismuth Alloy Electrodeposition from Chlorometalate Salts in Deep Eutectic Solvents

      Dr. Luciana Vieira, Dr. Jennifer Burt, Dr. Peter W. Richardson, Daniel Schloffer, David Fuchs, Alwin Moser, Prof. Philip N. Bartlett, Prof. Gillian Reid and Prof. Bernhard Gollas

      Version of Record online: 13 APR 2017 | DOI: 10.1002/open.201700045

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      More complex: For the first time, chlorometalate salts are used as precursors in the electrodeposition of alloys from deep eutectic solvents. The reduction of the complexes and the nucleation of Sn and Bi are studied and the biphasic alloys are characterized.

    2. You have full text access to this OnlineOpen article
      Heterobifunctional Dyes: Highly Fluorescent Linkers Based on Cyanine Dyes

      Virginia Wycisk, Dr. Katharina Achazi, Dr. Ole Hirsch, Christian Kuehne, Dr. Jens Dernedde, Prof. Dr. Rainer Haag and Dr. Kai Licha

      Version of Record online: 13 APR 2017 | DOI: 10.1002/open.201700013

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      It's do or dye: The synthesis of heterobifunctional linkers based on cyanine dyes is presented. The water-soluble dyes are used as rigid fluorescent linkers for macromolecules, here exemplified for an antibody and a polyethylene glycol (PEG) polymer. The fluorescent linkers have added value for the design of polymer and protein conjugates, and the conjugates can subsequently be applied in bioanalytical detection and imaging.

  7. Communications

    1. You have full text access to this OnlineOpen article
      Small-Molecule Dengue Virus Co-imprinting and Its Application as an Electrochemical Sensor

      Wannisa Sukjee, Chompoonuch Tancharoen, Prof. Dr. Pa-thai Yenchitsomanus, Dr. M. Paul Gleeson and Prof. Dr. Chak Sangma

      Version of Record online: 10 APR 2017 | DOI: 10.1002/open.201700037

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      Small molecule/dengue virus co-imprinting: Dengue virus can be used to fabricate molecularly co-imprinted polymers (MCIPs) of bisphenol A (BPA). The nanospheres of the virus particle enhance the number of active sites on the MCIP sensor. This leads to a higher sensitivity in electrochemistry impedance spectroscopy experiments compared to the sensors prepared with normal molecularly imprinted polymers.

    2. You have full text access to this OnlineOpen article
      Novel 5-(Benzo[b]thiophen-3-yl)pyridine-3-carbaldehyde (BTPA) Functionalization Framework For Modulating Fullerene Electronics

      Suru V. John, Dr. Christian C. De Filippo, Dr. Simone Silvestrini, Prof. Michele Maggini and Prof. Emmanuel Iwuoha

      Version of Record online: 4 APR 2017 | DOI: 10.1002/open.201600174

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      You've been framed: 3-(Benzo[b]thiophene-3yl)-5-fullero-1-methylpyrrolidinepyridine (BTFP) is revealed to be energetically like phenyl-C61-butyric-acid-methyl-ester (PCBM). BTFP exhibits close similarity to PCBM in terms of the first reduction potential values (−0.62 and −0.61 V vs. Ag/AgCl, for BTFP and PCBM, respectively) and lowest occupied molecular orbital energy level values (3.93 eV in both cases).

  8. Full Papers

    1. You have full text access to this OnlineOpen article
      Host–Guest Complexes of C-Ethyl-2-methylresorcinarene and Aromatic N,N′-Dioxides

      Dr. Rakesh Puttreddy, Dr. Ngong Kodiah Beyeh, Prof. Robin H. A. Ras and Prof. Kari Rissanen

      Version of Record online: 4 APR 2017 | DOI: 10.1002/open.201700026

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      NO need: C-Ethyl-2-methylresorcinarene forms 1:1 host–guest complexes with aromatic N,N′-dioxides through C−H⋅⋅⋅π interactions, only when every aromatic ring has an N-oxide group. Guest displacement competition experiments in solution lead to a clear ranking of guest selectivity according to 1H NMR analysis, which, in turn, is supported by solid-state X-ray crystallographic analysis.

    2. You have full text access to this OnlineOpen article
      Nature of the Ru−NO Coordination Bond: Kohn–Sham Molecular Orbital and Energy Decomposition Analysis

      Renato P. Orenha, Dr. Marcus V. J. Rocha, Prof. Dr. Jordi Poater, Prof. Dr. Sérgio E. Galembeck and Prof. Dr. F. Matthias Bickelhaupt

      Version of Record online: 30 MAR 2017 | DOI: 10.1002/open.201700028

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      Catch NO+: It is shown quantum chemically how trans-[RuCl(NO)(NH3)4]2+ is characterized by a RuII-NO+ coordination bond, which exists despite severe net electrostatic repulsion. The latter is, however, dominated by a strongly stabilizing synergy between RuII[RIGHTWARDS ARROW]NO+ π-backdonation and RuII[LEFTWARDS ARROW]NO+ σ-donation together with an RuII-NO+ stabilizing trans influence of the Cl ligand.

  9. Editorial

    1. You have full text access to this OnlineOpen article
      Virtual Issue: Advances in Electrochemistry

      Prof. Bernhard Gollas

      Version of Record online: 27 MAR 2017 | DOI: 10.1002/open.201700032

      Advances in Electrochemistry! This Virtual Issue on Advances in Electrochemistry highlights the rich diversity in the exciting and dynamic field of electrochemistry.

  10. Communications

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      Spin-Forbidden Branching in the Mechanism of the Intrinsic Haber–Weiss Reaction

      Ezequiel F. V. Leitão, Prof. Elizete Ventura, Prof. Miguel A. F. de Souza, Prof. José M. Riveros and Prof. Silmar A. do Monte

      Version of Record online: 23 MAR 2017 | DOI: 10.1002/open.201600169

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      The forbidden fruit: The gas-phase reaction between superoxide and hydrogen peroxide is studied at the theoretical level, and the major products are associated with a spin-forbidden pathway. Possible reasons for this preference are given in terms of characteristics of the calculated potential energy surfaces for the doublet and quartet states, including regions of crossing and near degeneracy between them.

    2. You have full text access to this OnlineOpen article
      Metalate-Mediated Functionalization of P4 by Trapping Anionic [Cp*Fe(CO)21-P4)] with Lewis Acids

      Jaap E. Borger, Maarten K. Jongkind, Dr. Andreas W. Ehlers, Dr. Martin Lutz, Dr. J. Chris Slootweg and Prof. Dr. Koop Lammertsma

      Version of Record online: 23 MAR 2017 | DOI: 10.1002/open.201700027

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      P4 functionalization: Reacting P4 with [Cp*Fe(CO)2] (Cp*=C5(CH3)5) in the presence of bulky Lewis acids (LAs) grants unprecedented access to unique transition-metal-substituted LA-stabilized bicyclic tetraphosphide anions 1 (LA=B(C6F5)3 (a) or BPh3 (b)). Their P-nucleophilic site (see HOMO 1 a) can be protonated to afford transient LA-free exo,endo- and exo,exo-Cp*Fe(CO)21-P4H) 2, allowing controllable stepwise metalate-mediated functionalization of P4.

  11. Full Papers

    1. You have full text access to this OnlineOpen article
      Synthesis and Detonation Properties of 5-Amino-2,4,6-trinitro-1,3-dihydroxy-benzene

      Xingcheng Zhang, Hualin Xiong, Hongwei Yang and Prof. Dr. Guangbin Cheng

      Version of Record online: 22 MAR 2017 | DOI: 10.1002/open.201600132

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      Off with a bang! 5-Amino-4,6-dinitro-1,3-dihydroxy-benzene (6) is synthesized through a ring-opening reaction of macrocyclic compound 4 with the aid of VNS (vicarious nucleophilic substitution of hydrogen) reaction conditions.

  12. Communications

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      Convenient and General Zinc-Catalyzed Borylation of Aryl Diazonium Salts and Aryltriazenes under Mild Conditions

      Dr. Xinxin Qi, Li-Bing Jiang, Chao Zhou, Dr. Jin-Bao Peng and Prof. Dr. Xiao-Feng Wu

      Version of Record online: 16 MAR 2017 | DOI: 10.1002/open.201700036

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      Mild mannered: A convenient and practical zinc-catalyzed borylation of aryldiazonium tetrafluoroborate salts and aryltriazenes with B2pin2 as the boron source is developed. No additional ligands or additives are required. A variety of arylboronates are isolated in moderate-to-excellent yields under mild reaction conditions.

  13. Cover Profiles

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      Self-Supported Polypyrrole/Polyvinylsulfate Films: Electrochemical Synthesis, Characterization, and Sensing Properties of Their Redox Reactions

      Dr. Toribio F. Otero, Lluis X. Martinez-Soria, Johanna Schumacher, Dr. Laura Valero and Victor H. Pascual

      Version of Record online: 12 JAN 2017 | DOI: 10.1002/open.201700175

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      “Thick films of polypyrrole/polyvinylsulfate (PPy/PVS) are electrogenerated on steel electrodes, peeled off from the electrode, and used as self-supported electrodes. Both the charge and the energy consumed by the material redox reactions sense the working electrochemical conditions…” Learn more about the story behind the research featured on the front cover in this issue's Cover Profile. Read the corresponding article at 10.1002/open.201600139.

  14. Cover Pictures

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      Self-Supported Polypyrrole/Polyvinylsulfate Films: Electrochemical Synthesis, Characterization, and Sensing Properties of Their Redox Reactions

      Dr. Toribio F. Otero, Lluis X. Martinez-Soria, Johanna Schumacher, Dr. Laura Valero and Victor H. Pascual

      Version of Record online: 12 JAN 2017 | DOI: 10.1002/open.201700176

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      The Front Cover picture shows an electrochemical cell featuring its most important parts (top) as well as three representative cyclic voltammetric responses (bottom), displaying the electrolyte potential window, the monomer oxidation–polymerization potential range, and the polymer oxidation–reduction potential window.More information can be found in the Full Paper by T. F. Otero and co-workers (DOI: 10.1002/open.201600139).

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