Assessing covalency in the hydrogen bond zoo

Jennifer Newton writes about a hot ChemComm article for Chemistry World

Covalency, a term describing bonding by sharing electrons, divides opinion when mentioned alongside hydrogen bonding. Worried that the concept of hydrogen bonding has been getting fuzzier over time, scientists in Germany have sought a fresh look at the very nature of these bonds, and how much covalency they involve.

Richard Dronskowski and colleagues at RWTH Aachen University collected evidence from hydrogen-bonded molecular crystals to elucidate how these crystals are held together and compare the covalency of long and short hydrogen bonds.


Read the full article in Chemistry World»

Read the original journal article in ChemComm – it’s free to access until 13th November:
Covalency of hydrogen bonds in solids revisited
Volker L. Deringer, Ulli Englert and Richard Dronskowski  
Chem. Commun., 2014,50, 11547-11549, DOI: 10.1039/C4CC04716H

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Top 25 ChemComm articles April–June 2014

We are delighted to share with you the top 25 most downloaded articles in ChemComm from April–June 2014. 

Top 25 most downloaded ChemComm articles for Q2 2014

Nanoparticles act as protein carriers during cellular internalization
Gerard W. Doorley and Christine K. Payne
DOI: 10.1039/C2CC16937A

Alzheimer’s disease amyloid beta converting left-handed Z-DNA back to right-handed B-form
Jie Geng, Chuanqi Zhao, Jinsong Ren and Xiaogang Qu
DOI: 10.1039/C0CC02049D

Polyfunctional benzylic zinc chlorides by the direct insertion of magnesium into benzylic chlorides in the presence of LiCl and ZnCl2
Albrecht Metzger, Fabian M. Piller and Paul Knochel
DOI: 10.1039/B812396A

Proton-regulated rectified ionic transport through solid-state conical nanopores modified with phosphate-bearing polymer brushes
Basit Yameen, Mubarak Ali, Reinhard Neumann, Wolfgang Ensinger, Wolfgang Knoll and Omar Azzaroni
DOI: 10.1039/B920870D

Wet chemical synthesis of silver nanorods and nanowires of controllable aspect ratio
Nikhil R. Jana, Latha Gearheart and Catherine J. Murphy
DOI: 10.1039/B100521I

Self-assembly of functional columnar liquid crystals
Takashi Kato, Takuma Yasuda, Yuko Kamikawa and Masafumi Yoshio
DOI: 10.1039/B816624B

Multifunctional catalysis by Pd-polyoxometalate: one-step conversion of acetone to methyl isobutyl ketone
Robert D. Hetterley, Elena F. Kozhevnikova and Ivan V. Kozhevnikov
DOI: 10.1039/B515325E

A robust, catalytic metal–organic framework with open 2,2′-bipyridine sites

Honghan Fei and Seth M. Cohen
DOI: 10.1039/C4CC01607F

Examination of native chemical ligation using peptidyl prolyl thioesters
Takahiro Nakamura, Akira Shigenaga, Kohei Sato, Yusuke Tsuda, Ken Sakamoto and Akira Otaka
DOI: 10.1039/C3CC47228K

Photo- and electro-chromism of diarylethene modified ITO electrodes—towards molecular based read–write–erase information storage
Jetsuda Areephong, Wesley R. Browne, Nathalie Katsonis and Ben L. Feringa
DOI: 10.1039/B608502D

Aggregation-induced emission: phenomenon, mechanism and applications
Yuning Hong, Jacky W. Y. Lam and Ben Zhong Tang
DOI: 10.1039/B904665H

Direct arylation of pyridines without the use of a transition metal catalyst
Yahui Li, Wei Liu and Chunxiang Kuang
DOI: 10.1039/C4CC02546F

One-pot synthesis of magnetic particle-embedded porous carbon composites from metal–organic frameworks and their sorption properties
Hee Jung Lee, Won Cho, Eunji Lim and Moonhyun Oh
DOI: 10.1039/C4CC01914H

Interaction of modified liposomes with Bacillus spores
Sergey Kazakov, Marian Kaholek, Tao Ji, Charles L. Turnbough, Jr and Kalle Levon
DOI: 10.1039/B312389H

A facile one-pot method to high-quality Ag-graphene composite nanosheets for efficient surface-enhanced Raman scattering
Zhe Zhang, Fugang Xu, Wenshu Yang, Mingyi Guo, Xiaodan Wang, Bailin Zhang and Jilin Tang
DOI: 10.1039/C1CC11125F

Graphene quantum dots: emergent nanolights for bioimaging, sensors, catalysis and photovoltaic devices

Jianhua Shen, Yihua Zhu, Xiaoling Yang and Chunzhong Li
DOI: 10.1039/C2CC00110A

Nitrogen-doped carbon nanotubes and graphene composite structures for energy and catalytic applications
Won Jun Lee, Uday Narayan Maiti, Ju Min Lee, Joonwon Lim, Tae Hee Han and Sang Ouk Kim
DOI: 10.1039/C4CC00146J

Novel hole transporting materials with a linear π-conjugated structure for highly efficient perovskite solar cells
Junjie Wang, Shirong Wang, Xianggao Li, Lifeng Zhu, Qingbo Meng, Yin Xiao and Dongmei Li
DOI: 10.1039/C4CC01637H

Metal-free oxidative synthesis of quinazolinones via dual amination of sp3 C–H bonds

Dan Zhao, Teng Wang and Jian-Xin Li
DOI: 10.1039/C4CC02648A

A dual functional additive for the HTM layer in perovskite solar cells
Hong Zhang, Yantao Shi, Feng Yan, Liang Wang, Kai Wang, Yujin Xing, Qingshun Dong and Tingli Ma
DOI: 10.1039/C3CC49458F

Copper-catalyzed olefinic C–H difluoroacetylation of enamides
Gilles Caillot, Jérémy Dufour, Marie-Charlotte Belhomme, Thomas Poisson, Laurence Grimaud, Xavier Pannecoucke and Isabelle Gillaizeau
DOI: 10.1039/C4CC01994F

Room-temperature Cu(II)-catalyzed aromatic C–H azidation for the synthesis of ortho-azido anilines with excellent regioselectivity

Yunpeng Fan, Wen Wan, Guobin Ma, Wei Gao, Haizhen Jiang, Shizheng Zhu and Jian Hao
DOI: 10.1039/C4CC01481B

Metal-mediated transformations of small molecules
Louise A. Berben and Jason B. Love
DOI: 10.1039/C4CC90123A
From themed collection Metal-Mediated Transformations of Small Molecules

A highly efficient mesoscopic solar cell based on CH3NH3PbI3−xClx fabricated via sequential solution deposition
Yingzhuang Ma, Lingling Zheng, Yao-Hsien Chung, Saisai Chu, Lixin Xiao, Zhijian Chen, Shufeng Wang, Bo Qu, Qihuang Gong, Zhaoxin Wu and Xun Hou
DOI: 10.1039/C4CC01962H

Reduction of graphene oxide viaL-ascorbic acid
Jiali Zhang, Haijun Yang, Guangxia Shen, Ping Cheng, Jingyan Zhang and Shouwu Guo
DOI: 10.1039/B917705A 


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Hot ChemComm articles for September

All of the referee-recommended articles below are free to access until 15th October 2014

A convergent rhodium-catalysed asymmetric synthesis of tetrahydroquinolines
Ho Yin Li, Joachim Horn, Amanda Campbell, David House, Adam Nelson and Stephen P. Marsden  
Chem. Commun., 2014,50, 10222-10224
DOI: 10.1039/C4CC04940C, Communication
From themed collection In Celebration of Richard Taylor’s 65th Birthday


On-surface aryl–aryl coupling via selective C–H activation
Qiang Sun, Chi Zhang, Huihui Kong, Qinggang Tan and Wei Xu  
Chem. Commun., 2014,50, 11825-11828
DOI: 10.1039/C4CC05482B, Communication


A single molecular probe for multi-analyte (Cr3+, Al3+ and Fe3+) detection in aqueous medium and its biological application
Junfeng Wang, Yingbo Li, Nikul G. Patel, Ge Zhang, Demin Zhou and Yi Pang  
Chem. Commun., 2014, Advance Article
DOI: 10.1039/C4CC04731A, Communication


Disentangling scalar coupling patterns by real-time SERF NMR
Nina Gubensäk, Walter M. F. Fabian and Klaus Zangger  
Chem. Commun., 2014, Advance Article
DOI: 10.1039/C4CC05892E, Communication


Isolation of stable non cyclic 1,2-disulfoxides. Revisiting the thermolysis of S-aryl sulfinimines
José A. Souto, Willian Lewis and Robert A. Stockman  
Chem. Commun., 2014, Advance Article
DOI: 10.1039/C4CC05751A, Communication


Chemical Reaction-Induced Multi-molecular Polarization (CRIMP)
Youngbok Lee, Niki M Zacharias, David Piwnica-Worms and Pratip K Bhattacharya  
Chem. Commun., 2014, Accepted Manuscript
DOI: 10.1039/C4CC06199C, Communication

 

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Antimalarial flow synthesis closer to commercialisation

Elisabeth Ratcliffe writes about a hot ChemComm article for Chemistry World

Scientists in Germany have demonstrated the large scale and inexpensive production of a range of antimalarial drugs, using a continuous flow system.

The processes yields several artemisinin-derived APIs that are key components in Artemisinin Combination Therapies

An important starting material for various anti-malarial drugs is artemisinin, which until recently could only be obtained by extraction from the plant Artemisia annua. As Peter Seeberger, from the Max Planck Institute for Colloids and Interfaces in Potsdam, explains, ‘the problem is that the drug is too expensive, such that in Africa and south east Asia between 40 and 50% of the artemisinin combination therapies are fake.’


Read the full article in Chemistry World»

Read the original journal article in ChemComm:
Continuous synthesis of artemisinin-derived medicines
Kerry Gilmore, Daniel Kopetzki, Ju Weon Lee, Zoltán Horváth, D. Tyler McQuade, Andreas Seidel-Morgenstern and Peter H. Seeberger  
Chem. Commun., 2014, Advance Article, DOI: 10.1039/C4CC05098C

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Optimising multi-enzyme reactions – enabling enzymatic encoding

Iain Larmour is a guest web writer for ChemSci. He has researched a wide variety of topics during his years in the lab including nanostructured surfaces for water repellency and developing nanoparticle systems for bioanalysis by surface enhanced optical spectroscopies. He currently works in science management. In his spare time he enjoys reading, photography, art and inventing.

The ability to mimic cascade and linked enzyme reactions has potential applications for disease diagnosis and pharmaceutical manufacturing, to name just two. However, the optimisation of the ratios of the interacting enzymes can be a time consuming step when carried out using standard solution based enzyme assays. With the problem becoming exponentially more difficult with the number of enzymes in the system, Jun Ge and Zheng Liu of the Department of Chemical Engineering at Tsinghua University, with colleagues, have looked to overcome this hurdle by developing a simple, fast and high throughput method based on ink-jet printing. 

The team replaced the colour inks in a standard inkjet printer with enzyme and substrate solutions. The ratio of these solutions could be controlled by varying the overall colour that was printed. Optimisation of cascade and coupled enzymatic reactions could be carried out rapidly and inexpensively compared to the standard solution based method. 

Enzymatic encryption, decoding and deletion of information

Precise two-dimensional control of enzyme placement via ink-jet printing also raises the possibility of creating 2D codes with enzymatic encryption built in, as the figure demonstrates. I don’t want to give the secret of this encryption technique away so you’ll have to read the paper today. 

To read the details, check out the ChemComm article in full: 

Ink-jet printing an optimal multi-enzyme system
Yifei Zhang, Fengjiao Lyu, Jun Ge, Zheng Liu
Chem. Commun., 2014, Accepted Article
DOI: 10.1039/C4CC06158F 

 

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Improvements to a selective hydrogenation process using ionic liquids

In this ChemComm communication, Peter Claus and co-workers describe an interesting application of room temperature ionic liquids to the selective hydrogenation of 2-hexyne. Unlike many reports in the literature, where an ionic liquid acting as a solvent may enhance a particular reaction, this report outlines a solid supported catalyst system modified with an ionic liquid layer.

Such materials, known as SCILLS, (solid catalyst with an ionic liquid layer) have been investigated in a variety of hydrogenation reactions. In this work the desired reaction is the reduction of 2-hexyne to cis-2-hexene. The catalyst is 1 wt% palladium on silica, modified with various loadings of 3 common ionic liquids: BMIM hexafluorophosphate, BMIM bis(triflouoromethanesulfonyl)imide and N-butyl-N-methylpyrrolidinium dicyanamide ([BMPL][DCA]). The performance of the unmodified catalyst was compared with the yield and selectivity afforded by the SCILL systems. The best results were reported with the dicyanamide ionic liquid SCILL, ([BMPL][DCA]) at 30 wt% ionic liquid loading.

In such a process, there are several reactions that must be suppressed. As the product is an olefin, isomerisation to the trans product must be controlled, as must further hydrogenation to the fully reduced material, hexane. For a number of reasons, based on the nature and amount of chemisorbed hydrogen, and favourable dicyanamide anion interactions with palladium, the dicyanamide SCILL system is particularly effective.

Notably, this system gives improved performance in terms of selectivity and yield over the two best performing commercial catalysts for this task. For example, Lindlar´s catalyst, palladium on calcium carbonate, deactivated with lead, cannot match its performance. In this work, the authors give an example of how ionic liquids can add value to a commercial process, while also offering considerable process improvements, in terms of toxicity and arguably, simplicity. The group’s focus now turns to SCILL activity and stability in a continuous hydrogenation process.

Read this RSC Chemical Communication today!

ionic-liquid layer
Frederick Schwab, Natascha Weidler, Martin Lucas and Peter Claus
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Inducing β-Peptide Structures from the Inside Out

Researchers from Japan have shown that fluoridation of β-peptide chains can influence their stability. Anthea Blackburn writes more…

The synthesis of tailor-made peptide chains represents a powerful tool for tuning the structure and properties of peptides, allowing for the development of  analogues for medical, technological and synthetic purposes.

For example, the β-peptide is a synthetic peptide, which, in contrast to its naturally-occurring α-peptide analogue, is bonded through the β-carbon rather than the α-carbon. As a result of this seemingly small structural change, alterations in the peptide’s secondary structure and thermodynamic stability are observed.

Adding fluoride groups to peptide chains represents another way to alter and stabilise the folding structure through the presence of stronger hydrogen bonds and the introduction of fluorophilicity. This approach is generally employed for the addition of fluoride groups at ‘remote positions,’ spaced two or more methylene units from the peptide backbone. However, this method has less of an effect on the conformation of the peptide itself, and instead primarily influences the tertiary and quaternary self-aggregation of peptide chains, as a result of the fluorophilic effect of the functionalised peptide chains.

Much less commonly studied is the effect of incorporating fluorine groups in ‘direct proximity’ to the peptide chain, that is, directly attached to the β-carbon, where it is proposed that the intramolecular hydrogen bonding will be directly affected, and consequently, so too will the secondary structure of the peptide chain.

Yasuhiro Ishida and co-workers from the RIKEN Center for Emergent Matter Science have  shown that this ‘direct’ fluorination of β-peptides can, in fact, affect the higher order structures of these peptide chains. Specifically, a hexameric β-peptide was designed, which consisted of cyclohexane-based β-amino acids in the 1-,3-,4- and 6-positions and L-alanine derivatives in the 2- and 5-positions, where the L-alanine methyl groups were either native or perfluorinated.

Irrespective of the degree of perfluorination in the β-peptide, it was found that the chains were arranged in the same left-handed 14-helix structure, with the NH-amide of the second and fifth residues participating in stabilising intramolecular H-bonding interactions. Moreover, it was found that although the presence of fluoride groups did not noticeably alter the overall secondary structure of the β-peptide chains, the stability of these structures was dramatically enhanced, showing the significant effect that fluoride groups can have on the hydrogen-bond donating ability of NH-amides.

This new approach of modifying peptide chains offers an interesting method  for influencing the secondary, and higher order, structures of the compounds, as well as their kinetic and thermodynamic properties. The effect of these structural modifications offers the possibility of tuning the chemical and biological properties of these peptide chains for use in new types of antibiotics and synthetic systems.

Read this HOT ChemComm article in full!

Stabilization of β-peptide helices by direct attachment of trifluoromethyl groups to peptide backbones
Joonil Cho, Kyohei Sawaki, Shinya Hanashima, Yoshiki Yamaguchi, Motoo Shiro, Kazuhiko Saigo and Yasuhiro Ishida
Chem. Commun., 2014, 50, 9855–9858.

About the Writer

Anthea Blackburn is a guest web writer for Chemical Communications. Anthea is a graduate student hailing from New Zealand, studying at Northwestern University in the US under the tutelage of Prof. Fraser Stoddart (a Scot), where she is exploiting supramolecular chemistry to develop multidimensional systems and study the emergent properties that arise in these superstructures. When time and money allow, she is ambitiously attempting to visit all 50 US states before graduation.

 

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Hot ChemComm articles for August

All of the referee-recommended articles below are free to access until 17th September 2014

Nanoscale insight into C–C coupling on cobalt nanoparticles
E. A. Lewis, C. J. Murphy, A. Pronschinske, M. L. Liriano and E. C. H. Sykes  
Chem. Commun., 2014,50, 10035-10037
DOI: 10.1039/C4CC03678F, Communication
From themed collection Scanning Probe Studies of Molecular Systems


A bifunctional curcumin analogue for two-photon imaging and inhibiting crosslinking of amyloid beta in Alzheimer’s disease
Xueli Zhang, Yanli Tian, Peng Yuan, Yuyan Li, Mohammad A. Yaseen, Jaime Grutzendler, Anna Moore and Chongzhao Ran  
Chem. Commun., 2014, Advance Article
DOI: 10.1039/C4CC03731F, Communication


Rapid engineering of versatile molecular logic gates using heterologous genetic transcriptional modules
Baojun Wang and Martin Buck  
Chem. Commun., 2014, Advance Article
DOI: 10.1039/C4CC05264A, Communication


Geometric and redox flexibility of pyridine as a redox-active ligand that can reversibly accept one or two electrons
Richard A. Lewis, K. Cory MacLeod, Brandon Q. Mercado and Patrick L. Holland  
Chem. Commun., 2014, Advance Article
DOI: 10.1039/C4CC05495D, Communication
From themed collection Non-Innocent Ligands


Targeted theranostic prodrugs based on an aggregation-induced emission (AIE) luminogen for real-time dual-drug tracking
Youyong Yuan, Ryan T. K. Kwok, Ruoyu Zhang, Ben Zhong Tang and Bin Liu  
Chem. Commun., 2014, Advance Article
DOI: 10.1039/C4CC05255B, Communication


Anion–π interactions and positive electrostatic potentials of N-heterocycles arise from the positions of the nuclei, not changes in the π-electron distribution
Steven E. Wheeler and Jacob W. G. Bloom  
Chem. Commun., 2014, Advance Article
DOI: 10.1039/C4CC05304D, Communication 

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Radiolabels help evaluate emerging cancer treatment

Laura Fisher writes about a hot ChemComm article for Chemistry World

Researchers in Spain have come up with a way to track the biodistribution of a boron cluster complex used to prepare boron-carrier drugs for a prospective cancer treatment called boron neutron capture therapy (BNCT).

Drugs based on the boron cluster complex COSAN (cobaltabisdicarbollide) exploit the over-expression of membrane receptors in cancer cells to deliver therapeutic levels of 10B across the membrane. Although 10B is a stable isotope, when a beam of low-energy neutrons is applied to the cell, 10B captures a neutron and subsequently decays, releasing a high-energy α-particle and destroying the cell.


Read the full article in Chemistry World»

Read the original journal article in ChemComm – it’s free to access until 26th September:
COSAN as a molecular imaging platform: synthesis and “in vivo” imaging
Kiran B. Gona, Adnana Zaulet, Vanessa Gómez-Vallejo, Francesc Teixidor, Jordi Llop and Clara Viñas  
Chem. Commun., 2014, Advance Article, DOI: 10.1039/C4CC05058D, Communication

 
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ChemComm’s Impact Factor reaches another record high – 6.7

The latest citation data released by Thomson Reuters reveals that ChemComm’s Impact Factor has risen once again this year to 6.718.

Coupled with fast publication times and great author service, these impressive trends underline the continuing success of ChemComm as the largest publisher of high quality communications within the general chemistry arena.  You can read some of our most highly cited articles listed below.

Thank you to all who have contributed to the journal’s success so far – our authors, referees, readers and Editorial and Advisory Boards – we are very grateful for your support.

We invite you to submit your next urgent Communication to ChemComm.

Find out how other Royal Society of Chemistry journals are ranked in the latest Impact Factor release

Top cited ChemComm articles:

Feature Articles

Graphene quantum dots: emergent nanolights for bioimaging, sensors, catalysis and photovoltaic devices
Jianhua Shen, Yihua Zhu, Xiaoling Yang and Chunzhong Li

Diketopyrrolopyrrole (DPP)-based materials for organic photovoltaics
Sanyin Qu and He Tian

Enhancing the performances of Li-ion batteries by carbon-coating: present and future Huiqiao Li and Haoshen Zhou

Communications

One-step synthesis of amino-functionalized fluorescent carbon nanoparticles by hydrothermal carbonization of chitosan
Yunhua Yang, Jianghu Cui, Mingtao Zheng, Chaofan Hu, Shaozao Tan, Yong Xiao, Qu Yang and Yingliang Liu

Graphene-enveloped sulfur in a one pot reaction: a cathode with good coulombic efficiency and high practical sulfur content
Scott Evers and Linda F. Nazar

Carbon nanodots as fluorescence probes for rapid, sensitive, and label-free detection of Hg2+ and biothiols in complex matrices
Li Zhou, Youhui Lin, Zhenzhen Huang, Jinsong Ren and Xiaogang Qu

Hierarchical porous NiCo2O4 nanowires for high-rate supercapacitors
Hao Jiang, Jan Ma and Chunzhong Li

*The Impact Factor provides an indication of the average number of citations per paper. Produced annually, Impact Factors are calculated by dividing the number of citations in a year, by the number of citeable articles published in the preceding two years. Data based on 2013 Journal Citation Reports®, (Thomson Reuters, 2014).

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