Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science

Australian Journal of Chemistry

Australian Journal of Chemistry

Australian Journal of Chemistry - an International Journal for Chemical Science publishes research papers from all fields of chemical science, with a focus on multidisciplinary chemistry and emerging areas of research. Read more about the journalMore

Editors-in-Chief: George Koutsantonis and John Wade

Current Issue

Australian Journal of Chemistry

Volume 69 Number 12 2016

RACI and AAS Awards

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Wine is a fascinating natural product containing many hundreds of volatile compounds. A much smaller number of key compounds typically contribute to wine aroma, and odorants with characteristic aroma qualities may even define a particular varietal wine. Examples include the varietal thiols, present as odourless precursors in grape berries, that typify the aroma of Sauvignon Blanc wine.

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Transition metal-mediated arylation is emerging as a powerful tool for the covalent modification of native peptides and proteins. This highlight review will summarize recent advances in the regio- and chemoselective arylation of select proteinogenic side chains and backbone amide N–H bonds with special focus on the application of these methodologies in the field of bioconjugation.

CH16428Masked Ketenes as Dienophiles in the Diels–Alder Reaction

Emily G. Mackay and Christopher G. Newton
pp. 1365-1374
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The Diels–Alder reaction is one of the most powerful, well-established, and versatile reactions in organic chemistry; however, its application in certain settings remains a challenge as a result of functional group incompatibility. In this review, we examine the methods in which masked ketenes can be employed as dienophiles, taking particular note of applications in complex settings.

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Because it is an ozone-depleting substance, carbon tetrachloride is slowly disappearing from laboratories but it is still used in industry. There is more carbon tetrachloride in the upper atmosphere than can be accounted for by estimated releases from anthropogenic activities. The figure shown is adapted, with permission of the authors, from a recent report.

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The elasticity of a range of vertebrate and particularly human tissues depends on the dynamic and persistent protein, elastin, which is predominantly made by assembling tropoelastin. This overview considers tropoelastin’s molecular features and biological interactions in the context of its value in tissue repair.

CH16443Binder-Free TiO2 Monolith-Packed Pipette Tips for the Enrichment of Phosphorylated Peptides

Chang Lei, Liang Zhou, Chun Xu, Xiaoran Sun, Amanda Nouwens and Chengzhong Yu
pp. 1396-1401
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A macroporous TiO2 monolith-entrapped pipette-tip was developed for phosphorylated peptide enrichment with a detection limit of 1 ng mL–1 and better enrichment efficiency compared with a commercial tip.

CH16430Effect of Modification Protocols on the Effectiveness of Gold Nanoparticles as Drug Delivery Vehicles for Killing of Breast Cancer Cells

Zahrah Alhalili, Daniela Figueroa, Martin R. Johnston, Joe Shapter and Barbara Sanderson
pp. 1402-1412
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Functionalised gold nanoparticles (AuNPs) for the delivery of chemotherapy agent Taxol to breast cancer cells (T47D) have been tested using various nanoparticle modification protocols.

CH16447A Derivation of the Gibbs Equation and the Determination of Change in Gibbs Entropy from Calorimetry

Denis J. Evans, Debra J. Searles and Stephen R. Williams
pp. 1413-1419
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Building on our equilibrium relaxation theorem for systems in contact with a heat reservoir, we derive Gibbs’ equation, the fundamental equation of classical equilibrium thermodynamics. We reinforce that Clausius’ inequality contains terms that were undefined by Clausius and show the change in Gibbs entropy can be expressed in terms of physical quantities.

Online Early

The peer-reviewed and edited version of record published online before inclusion in an issue

Published online 09 December 2016

CH16559Synthesis of Norfijimycin A with Activity against Mycobacterium tuberculosis

Alexander Stoye, Gayathri Nagalingam, Warwick J. Britton and Richard J. Payne
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Fijimycin A is a cyclic depsipeptide that has been shown to possess activity against a range of pathogenic bacteria. This communication describes the total synthesis of norfijimycin A, a simplified analogue of the marine natural product fijimycin A. The natural product analogue was shown to possess significant activity against Mycobacterium tuberculosis, the etiological agent of tuberculosis.

Published online 30 November 2016

CH16584Structural Systematics for Lanthanide(III) Systems: Interactions of the Achiral Hexamminecobalt(III) Cation with Tris(dipicolinato)lanthanate(III) Anions

Jack M. Harrowfield, Irene Ling, Brian W. Skelton, Alexandre N. Sobolev and Allan H. White
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Structures of [Co(NH3)6][Ln(dipic)3] hydrates have been analysed in terms of the weak interactions occurring between the achiral cation and the chiral anions.

Published online 29 November 2016

CH16554Effective Dissolution of Biomass in Ionic Liquids by Irradiation of Non-Thermal Atmospheric Pressure Plasma

Kosuke Kuroda, Kai Shimomura, Tatsuo Ishijima, Kenji Takada, Kazuaki Ninomiya and Kenji Takahashi
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Lignocellulose has gained much interest as a potential renewable energy resource. However, it is hardly soluble. In this study, a non-thermal plasma was applied to dissolution of lignocellulose to ionic liquids. Chemically active species, which were generated by the plasma, induced decomposition of the lignin network, and consequently dissolution of biomass into ionic liquids was accelerated.

Published online 25 November 2016

CH16510Molecular Insights into the Interaction Between the SPRY Domain-Containing SOCS Box Protein SPSB2 and Peptides Based on the Binding Motif from iNOS

Eleanor W. W. Leung, Mark D. Mulcair, Beow Keat Yap, Sandra E. Nicholson, Martin J. Scanlon and Raymond S. Norton
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Surface plasmon resonance and NMR spectroscopy were used to gain insights into the binding of iNOS-derived peptides to SPSB2. The complex interplay of peptide sequence and protein binding will inform efforts to design peptide therapeutics to disrupt the iNOS–SPSB interaction.

Published online 25 November 2016

CH16537Dehydrogenative Coupling of Hydrosilanes and Alcohols by Alkali Metal Catalysts for Facile Synthesis of Silyl Ethers

Adimulam Harinath, Jayeeta Bhattacharjee, Srinivas Anga and Tarun K. Panda
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The RO–H/H–Si cross-dehydrogenative coupling (CDC) of alcohols and hydrosilanes with high yield (up to 99 %) and chemoselectivity for the production of silyl ethers using alkali metal salts [MN(SiMe3)2] (M = Li, Na, K) as pre-catalysts and under ambient conditions is presented.

Published online 24 November 2016

CH16589Synthesis and Protein Engineering Applications of Cyclotides

Haiou Qu, Bronwyn J. Smithies, Thomas Durek and David J. Craik
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Cyclotides are a group of cysteine-rich peptides derived from plants. Their exceptional stability based on their head-to-tail cyclized backbone and cystine knot, together with their tolerance to sequence modifications, make them promising drug design scaffolds into which novel bioactive sequences may be grafted. These grafting applications are achievable by solid-phase peptide synthesis. This article describes recent developments in the chemical synthesis and enzyme-mediated cyclization of cyclotides.

Published online 16 November 2016

CH16562Aptamer-Based Fluorescent Switch for Sensitive Detection of Oxytetracycline

Mahsa Babaei, Seyed Hamid Jalalian, Hadi Bakhtiari, Mohammad Ramezani, Khalil Abnous and Seyed Mohammad Taghdisi
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In this paper, we introduce a novel aptasensor for fast detection of oxytetracycline (OTC), based on a triple helix molecular switch (THMS) complex formation. The limit of detection (LOD) of this sensor was 1.67 and 6.44 nM in phosphate buffer and milk samples, respectively. The sensor also showed a high selectivity towards OTC.

Published online 15 November 2016

CH16547Synthesis and Structures of Rare Earth 3-(4?-Methylbenzoyl)-propanoate Complexes – New Corrosion Inhibitors

Caspar N. de Bruin-Dickason, Glen. B. Deacon, Craig M. Forsyth, Schirin Hanf, Oliver B. Heilmann, Bruce R. W. Hinton, Peter C. Junk, Anthony E. Somers, Yu Qing Tan and David R. Turner
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A series of rare earth (RE) 3-(4′-methylbenzoyl)propanoate (mbp) complexes [RE(mbp)3(H2O)] (RE = Y, La, Ce, Nd, Ho, Er) have been prepared by either metathesis reactions between the corresponding rare earth chloride and Na(mbp) or protolysis of rare earth acetates by the free acid.

Published online 14 November 2016

CH16224Open-Chain Crown-Ether-Derived Two-Photon Fluorescence Probe for Real-Time Dynamic Biopsy of Mercury Ions

Chibao Huang, Daohai Zhang, Junle Qu, Xiaonan Liu, Guanglian Zhao, Tingxiang Yuan and Yang Liu
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The probe developed in the present study can selectively detect Hg2+ ions in live cells and living tissues without interference from other metal ions and the membrane-bound probes, and its quenching constant is 8.73 × 105 M–1.

Published online 10 November 2016

CH16532Macrocyclic Peptidomimetics Prepared by Ring-Closing Metathesis and Azide–Alkyne Cycloaddition

Ashok D. Pehere, Xiaozhou Zhang and Andrew D. Abell
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Ring-closing metathesis (RCM) and copper(i)-catalyzed azide–alkyne cycloaddition (CuAAC) are powerful strategies to introducing a macrocycle. This review focusses on the current synthetic approaches to access biologically active macrocycles that target important therapeutic aims for conditions such as cancer, cataracts, HIV, and neurological diseases.

Published online 09 November 2016

CH16357Ring-Opening Dispersion Polymerization of ʟ-Lactide with Polylactide Stabilizer in Supercritical Carbon Dioxide

Jinjun Deng, Shiping Zhan, Jingchang Wang, Zhijun Liu and Zhiyi Li
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The particle diameter distributions of PLLA show that the stabilizer S131 with short lipophilic segment could improve the particle diameter distribution range, compared with the long lipophilic segment of stabilizer S121. With increasing concentration of the stabilizer S131, the particle size decreased and particle distribution became narrow.

Published online 07 November 2016

CH16501Synthesis of Multicomponent Peptide-Based Vaccine Candidates against Group A Streptococcus

Waleed M. Hussein, Jiaxin Xu, Pavla Simerska and Istvan Toth
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A stepwise conjugation technique was employed to synthesise a multiantigenic vaccine candidate against Group A streptococcus (GAS) through azide–alkyne cycloaddition and mercapto–maleimide reactions. The final vaccine candidate consists of four different components: two GAS antigens, a T-helper epitope, and the lipidic moiety dipalmitoyl serine (DPS).

Published online 04 November 2016

CH16460Improved Extraction Yield of Citral from Lemon Myrtle Using a Cellulose-Dissolving Ionic Liquid

Koki Munakata, Masahiro Yoshizawa-Fujita, Masahiro Rikukawa and Toyonobu Usuki
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The extraction yield of citral from lemon myrtle using cellulose-dissolving ionic liquids was up to 2.1 times higher than that obtained using ethanol. The ionic liquid could be recycled and reused nine times for the extraction of citral.

Published online 04 November 2016

CH16527Coordination Behaviour of 1-(4,2′:6′,4′′-terpyridin-4′-yl)ferrocene and 1-(3,2′:6′,3′′-terpyridin-4′-yl)ferrocene: Predictable and Unpredictable Assembly Algorithms

Y. Maximilian Klein, Alessandro Prescimone, Edwin C. Constable and Catherine E. Housecroft
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1-(4,2′:6′,4″-Terpyridin-4′-yl)ferrocene offers a fixed V-shaped N,N″-donor set, but this does not lead to a predictable assembly algorithm; polymer and metalloamacrocycle formations compete. Similar competitive behaviour is observed in coordination assemblies based on 1-(4,2′:6′,4″-terpyridin-4′-yl)ferrocene, with the greater conformational flexibility of the latter adding to the non-predictability of the assembly process.

Published online 04 November 2016

CH16511Unique Functional Materials Derived from β-Amino Acid Oligomers

Mark P. Del Borgo, Ketav Kulkarni and Marie-Isabel Aguilar
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As demonstrated in the recent literature, β-peptides can self-assemble into a range of materials. This highlight explores recent developments in the preparation of functional materials involving β-peptides, wherein the self-assembly of β-peptides is unperturbed by side chain functionalisation and leads to the formation of stable gels and scaffolds that can support cellular growth.

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Hierarchical HZSM-5 were synthesised by controlled desilication in alkaline medium and used as catalyst for the selective oxidation of 2,3,6-trimethylphenol to 2,3,5-trimethyl-1,4-benzoquinone. The combined studies suggested that the nature of the solvent, intrinsic acidity, and shape selectivity of the hierarchical structure ensured high catalytic properties.

Published online 28 October 2016

CH16499An Efficient Chemical Synthesis of Lassomycin Enabled by an On-Resin Lactamisation–Off-Resin Methanolysis Strategy and Preparation of Chemical Variants

Paul W. R. Harris, Gregory M. Cook, Ivanhoe K. H. Leung and Margaret A. Brimble
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Lasso peptides contain a unique 3-D topography (known as a lariat knot) and are touted as novel scaffolds for biomedical applications. The synthesis of the non-threaded lasso peptide lassomycin was accomplished by solid-phase peptide chemistry and a novel way to install the C-terminal ester on the fully unprotected peptide.

Published online 26 October 2016

CH16347Synthesis and Evaluation of a Biocompatible Macromolecular Gadolinium Compound as a Liver-Specific Contrast Agent for MRI

Youyang Zhan, Rong Xue, Mengchao Zhang, Chuanling Wan, Xiaojing Li, Fengkui Pei, Changjiang Sun and Lin Liu
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Gadolinium complexes are widely applied as magnetic resonance imaging contrast agents. However, they have some undesirable properties, e.g. low relaxivity and target non-specificity. A new biocompatible macromolecular gadolinium compound has been synthesised as a liver-specific contrast agent. The ability to improve the imaging signal and the T1-relaxivity is satisfactory, and it has a long window imaging time with a low acute toxicity.

Published online 24 October 2016

CH16488Cope Rearrangement in Bicyclo[5.1.0]octa-2,5-diene and its Mono- and Di-Hetero Analogues: A DFT Study

Priya Yadav, Shilpa Yadav, Asha Gurjar and Raj K. Bansal
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Cope rearrangement of bicycle[5.1.0]octa-2,5-diene and its 8-hetero- (N,O,P) and 4,8-dihetero-analogues has been investigated in the gas phase at the B3LYP/6-31+G* level. The results reveal that relative stabilities of the three-membered ring undergoing opening and the three-membered ring being formed as a result of the Cope rearrangement determine the feasibility and rate of the rearrangement.

Published online 21 October 2016

CH16398A New Fluorometric Method for the Determination of Oxaliplatin Based on Cucurbit[7]uril Supramolecular Interaction

YinXia Chang, XueChao Duan, XiangMei Zhang, Fan Liu and LiMing Du
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The fluorescence intensity of CB[7]–PAL, CB[7]–BER, or CB[7]–COP system decreased with increasing amounts of oxaliplatin (l-OHP) added. The trend is attributed to the competition between l-OHP and PAL, BER, or COP molecules for occupancy of the CB[7] cavity.

Published online 20 October 2016

CH16406A Quantum Theory of Atoms-in-Molecules Perspective and DFT Study of Two Natural Products: Trans-Communic Acid and Imbricatolic Acid

Sarvesh Kumar Pandey, Mohammad Faheem Khan, Shikha Awasthi, Reetu Sangwan and Sudha Jain
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Intramolecular H···H as well as C···H non-covalent interactions have been retrieved and characterized using quantum theory of atoms-in-molecules and the computed chemical reactivity index using HOMO–LUMO gap and molecular electrostatic potential surface have been compared with experimentally observed bioactivity parameter.

Published online 19 October 2016

CH16288Preparation and Characterization of PA6-PEG/Li High Performance Static Dissipation Composites

Chongling Yang, Shouzai Tan, Gengen Chen and Litao Guan
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A series of novel PA6-PEG/Li composites were developed by melt blending the PA6-PEG copolymer (10 wt-% PEG) with three different kinds of colourless lithium salts (LiCl, C18H35LiO2, LiAc). The PA6-PEG/LiCl composite showed an excellent static dissipation performance of 2.71 × 108 Ω square–1.

Published online 17 October 2016

CH16407Synthesis of Multivalent [Lys8]-Oxytocin Dendrimers that Inhibit Visceral Nociceptive Responses

Jingjing Wan, Mehdi Mobli, Andreas Brust, Markus Muttenthaler, Åsa Andersson, Lotten Ragnarsson, Joel Castro, Irina Vetter, Johnny X. Huang, Mathias Nilsson, Stuart M. Brierley, Matthew A. Cooper, Richard J. Lewis and Paul F. Alewood
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We demonstrate efficient ‘click’ synthesis of large dendrimeric oxidatively folded peptides with up to 16 copies of [Lys8]-oxytocin that maintain potency and structure.

Published online 14 October 2016

CH16438Interpenetrated Double Pillared-Layer CoII MOFs with pcu Topology

In-Hyeok Park, Yunji Kang, Eunji Lee, Anjana Chanthapally, Shim Sung Lee and Jagadese J. Vittal
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The influence of organic backbone on the bonding modes of the dicarboxylates, conformations of the of the long and flexible dipyridyl ligand, and pore size in isoreticular metal–organic frameworks formed by three double pillared-layer CoII metal–organic frameworks with a pcu topology is discussed.

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Several indeno[1,2-c]pyridazines were efficiently synthesised using the one-pot, three-component reaction of substituted indanones, arylglyoxalmonohydrates, and hydrazine in the presence of 1,5-diazabicyclo[4,3,0]non-5-ene (DBN) in water at room temperature.

Published online 05 October 2016

CH16459Synthesis of a Tetraphenylethene-Substituted Tetrapyridinium Salt with Multifunctionality: Mechanochromism, Cancer Cell Imaging, and DNA Marking

Anushri Rananaware, Amanda N. Abraham, Duong Duc La, Vishal Mistry, Ravi Shukla and Sheshanath V. Bhosale
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A tetrapyridyl-substituted tetraphenylethylene (TPy-TPE) works as a good fluorescent visualiser for specific staining for cellular imaging and as a DNA marker.

Published online 03 October 2016

CH16425Atomic Force Microscopy Studies of the Interaction of Antimicrobial Peptides with Bacterial Cells

Anna Mularski and Frances Separovic
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Many antimicrobial peptides (AMPs) are membrane-active but their mode of action remains elusive. Most studies have been conducted with synthetic membrane systems but, more recently, atomic force microscopy has been utilized to reveal the effect of AMPs on bacterial cells and provide great insight into how this class of peptides lyse cells.

Published online 28 September 2016

CH16454Effect of Hydrogen Peroxide on the Extraction of Components of Cedar Powder with Tetrabutylphosphonium Hydroxide Aqueous Solution at 60°C

Sachiko Yamanaka, Koichi Yoshioka, Hisashi Miyafuji and Hiroyuki Ohno
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Cedar powder was treated with ionic liquids and onium hydroxide aqueous solution under very mild condition such as at 60°C. Addition of hydrogen peroxide accelerated the dissolution of lignin fragments with larger molecular weights owing to scission of the lignin network structure.

Published online 21 September 2016

CH16368Two 3D ZnII Metal–Organic Frameworks with 3- and 8-Fold Interpenetration: Syntheses, Structures, Photodegradation, and Photoluminescent Properties

Chuan-Bin Fan, Xiang-Min Meng, Yu-Hua Fan, Zi-Ao Zong, Xiao-Yin Zhang and Cai-Feng Bi
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Two novel zinc coordination polymers have been synthesised and characterised. Their topological structures show 4-connected 8- and 3-fold interpenetrating 3D frameworks. Furthermore, they exhibit good photodegradation capability and photoluminescence properties.

Published online 15 September 2016

CH16138Effect of Alkyl Chain Length of Imidazolium Cation on the Electroreduction of CO2 to CO on Ag Electrode in Acetonitrile

Qianqian Wang, Chengzhen Chen, Juhua Zhong, Bo Zhang and Zhenmin Cheng
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Effect of imidazolium cation (MIM+) on the electroreduction of CO2 to CO was investigated by linear sweep voltammetry (LSV), cyclic voltammetry (CV), constant potential electrolysis (CPE), and density functional theory (DFT) computations. It is interesting to find that the catalytic effect of MIM+ is sensitive to the alkyl chain length on its N1-position.

Published online 15 September 2016

CH16429Sweet Poisons: Synthetic Strategies towards Tutin Glycosides

Duong Nhu, Lesley Larsen, Nigel B. Perry, David S. Larsen and Bill C. Hawkins
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Various glycosylation reactions were tried in an effort to synthesise β-linked tutin glycosides, found in toxic honeys. Cationic palladium-mediated glycosylation gave the α-linked tutin tetrabenzyl glucoside (5 : 1, α : β). Hydrogenolysis of the benzyl ether groups resulted in tutin double-bond migration. Epoxide opening and rearrangement were observed upon acetylation of the tutin glucoside.

Published online 08 September 2016

CH16333Syntheses and Characterizations of Three Organically Templated Zinc Phosphites with 12-Ring Channels

Zhen-Zhen Bao, Song-De Han, Jin-Hua Li, Guo-Ming Wang and Zong-Hua Wang
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Three zinc phosphites have been synthesized and characterized. Their frameworks are constructed from 4-connected ZnO4 tetrahedra and 3-connected HPO3 pseudopyramids. There are 12-membered ring (12-MR) and 8-MR apertures in their (3,4)-connected network. Helical chains are observed in compound 3.

Published online 08 September 2016

CH16320Preparation of CoWO4/g-C3N4 and its Ultra-Deep Desulfurization Property

Pengfei Xing, Rongxiang Zhao, Xiuping Li and Xiaohan Gao
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CoWO4/g-C3N4 was synthesized by precipitation and calcination, and used as a catalyst for oxidative desulfurization. In the process, CoWO4/g-C3N4 showed excellent desulfurization activity and the desulfurization rate reached 92.9 %. Moreover, the catalyst could be recycled at least five times without any clear decrease in catalytic activity.

Published online 08 September 2016

CH16467Endocyclic and Endo–Exocyclic Silver(I) Complexes of Thiaoxaaza Macrocycles: Crystallographic and NMR Studies

Yunji Kang, Hyeong-Hwan Lee, Huiyeong Ju, Eunji Lee, Seulgi Kim, Joon-Hwa Lee, In-Hyeok Park and Shim Sung Lee
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Thiaoxaaza macrocycles incorporating NO2S2 (L1) and NO2S3 (L2) donors were employed and their silver(i) nitrate complexation in solid and solution states was investigated.

Published online 25 August 2016

CH16236Novel SrO-CaO Mixed Metal Oxides Catalyst for Ultrasonic-Assisted Transesterification of Jatropha Oil into Biodiesel

Syed Danish Ali, Isma Noreen Javed, Usman Ali Rana, Muhammad Faizan Nazar, Waqas Ahmed, Asifa Junaid, Mahmood Pasha, Rumana Nazir and Rizwana Nazir
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Novel strontium oxide/calcium oxide (SrO-CaO) mixed metal oxides heterogeneous catalyst is synthesized to highlight its catalytic potential for the transformation of Jatropha oil to green biofuels via an ultrasonic-assisted transesterification process.

Published online 22 August 2016

CH16180Synthesis of a Novel Dibenzylamide Derivative of p-tert-Octylcalix[4]arene and its Extraction Properties Towards Noble Metal Ions

Jee Young Kim, Yoga Priastomo, Shintaro Morisada, Hidetaka Kawakita, Keisuke Ohto and Yang Kim
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A N,N-dibenzylacetoamide derivative of p-tert-octylcalix[4]arene has been synthesised and its solvent extraction of precious metals in nitric acid media was investigated for determining the effects of extractant concentration and its contact time as well as nitric acid concentration in comparison with a N,N-diethylacetoamide derivative.

Published online 12 August 2016

CH16214Al2O3 Microspheres Prepared by Cathode Plasma Electrolysis

Chenxu Liu, Jin Zhang, Yedong He, Peng Wang, Shunjie Deng and Shuguang Zhang
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Al2O3 microspheres were prepared by cathode plasma electrolysis without additional heating treatment. The microspheres, with diameters of 5–30 μm, consisted of γ-Al2O3 and α-Al2O3. The mechanism and model were put forward in the formation process.

Published online 01 August 2016

CH16250Preparation of Magnetic Surface-Imprinted Polymer Microspheres with Hydrophilic External Layers for Selective Extraction of Fluoroquinolones from Eggs

Yun-Kai Lv, Xue Xiong, Fang-Fang Zhao, Meng-Zhe Li, Mian Wang and Xiao-Yang Li
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Novel restricted access media–molecularly imprinted magnetic microspheres that displayed water-compatibility, exclusion of biomacromolecules, and selective enrichment of analytes were prepared by a one-pot surface imprinting method for the magnetic dispersion microextraction of trace fluoroquinolones from egg samples.

Published online 29 July 2016

CH16239(Diacetoxyiodo)benzene: More Than an Oxidant

Rosana Helena C. N. Freitas
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Although PhI(OAc)2 is known as an oxidizing agent, it can also serve as a reagent or a catalyst in different types of chemical reactions in organic synthesis. PhI(OAc)2 is used in radical reactions, oxidation reactions, and in heterocycle synthesis. This paper reports some relevant and recent new uses of PhI(OAc)2.

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Poly(γ-4-methylbenzyl-L-glutamate) pyridinium tetrafluoroborate conjugates with constant main chain length, various pyridinium pendants, and high grafting efficiency can be readily prepared by nucleophilic substitution and ion-exchange reaction. They can exhibit reversible UCST-type phase behaviours in both methanol and water depending on the type of pyridinium pendants.

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This work involves the experimental and theoretical study of the nucleophilic substitution of meta- and para-substituted benzyl bromides with benzylamine.

Published online 12 July 2016

CH16270Anionic Ring Opening Polymerization of ε-Caprolactone Initiated by Lithium Silanolates

Angel J. Satti, Augusto G. O. de Freitas, M. Loreta Sena Marani, Marcelo A. Villar, Enrique M. Vallés, Cristiano Giacomelli and Andrés E. Ciolino
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This paper describes a simple way to synthesize poly(caprolactone) or poly(siloxane-block-caprolactone) copolymers through anionic polymerization by employing lithium silanolates.

Published online 08 July 2016

CH16213Mo(CO)6 as a Solid CO Source in the Synthesis of Aryl/Heteroaryl Weinreb Amides under Microwave-Enhanced Condition

Raghu Ningegowda, Savitha Bhaskaran, Ayyiliath M. Sajith, Chandrashekar Aswathanarayanappa, M. Syed Ali Padusha, Nanjunda Swamy Shivananju and Babu Shubha Priya
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The facile transformation of aryl/heteroaryl nonaflates into corresponding amides via Pd-catalyzed aminocarbonylation using Mo(CO)6 as a solid CO source under microwave-enhanced condition is reported. The method was found to be tolerant with respect to a diverse range of electronically biased aryl/heteroaryl nonaflates, and exceptional yields were obtained. The optimized protocol was further extended to a diverse range of amines.

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The kinetics of the nucleophilic substitution reactions of bis(N,N-diethylamino)phosphinic chloride with XC6H4NH2(D)2 are investigated in MeCN at 65.0°C. This study examines the substituent effects, deuterium kinetic isotope effects (DKIEs), and mechanism of the phosphoryl transfer reactions. A concerted SN2 mechanism involving the predominant backside attack is proposed.

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The generalized anomeric relationships in halocarbonyl isocyanates (13) and halocarbonyl azides (46) result from the cooperative effects of the hyperconjugative generalized anomeric effects (HC-GAE) and Pauli exchange-type repulsion (PETR). The electrostatic model associated with the dipole–dipole interactions (EM-DDI) and the attractive electrostatic interactions (AEIs) between the natural atomic charges have no significant effects on the conformational preferences in compounds 13 and 46.

Published online 27 June 2016

CH16228Rheopectic Gel Formation of Stimuli-Responsive Ionic Liquid/Water Mixtures

Yukinobu Fukaya, Takuro Nakano and Hiroyuki Ohno
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Ionic liquids are composed of ions only. However, they are not always completely soluble in water. Mixtures of phosphonium/phosphonate-type ionic liquids and water prepared herein exhibited stimuli-responsive phase transition, lower critical solution temperature phase transition, and thermoreversible viscosity change, and underwent rheopectic gelation depending on the water content

Published online 27 June 2016

CH16321Organometallic Complexes for Non-Linear Optics. 59. Syntheses and Optical Properties of Some Octupolar (N-Heterocyclic Carbene)gold Complexes

Gang Liu, Cristóbal Quintana, Genmiao Wang, Mahesh S. Kodikara, Jun Du, Rob Stranger, Chi Zhang, Marie P. Cifuentes and Mark G. Humphrey
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The nonlinear optical (NLO) coefficients of (triphenylphosphine)gold alkynyl complexes are better than those of (N-heterocyclic carbene)gold alkynyl complexes; calculations suggest that the key low-energy transitions are from the (phosphine)gold to the alkynyl ligand in the former, and from the Au-alkynyl group to NHC in the latter.

Published online 24 June 2016

CH16088Patterned Copper Sulfide Thin Films: a Method for Studying Leaching Behaviour

Rachel S. Brokenshire, Anthony Somers, Miao Chen and Angel A. J. Torriero
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This work presents a practical and simple alternative method for studying the leaching of copper from copper sulfide. It is demonstrated, for the first time, that micro-patterned thin films can be used as a model system for studying mineral leaching of copper-bearing minerals directly by measuring changes in the film thickness using white light interferometric profilometry and changes in the film morphology and elemental composition using scanning electron microscopy coupled with energy-dispersive X-ray spectroscopy.

Published online 23 June 2016

CH16241The Use of Hydrogels as Biomimetic Materials for 3D Cell Cultures

Eric Y. Du, Adam D. Martin, Celine Heu and Pall Thordarson
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Hydrogels have been gaining increasing popularity as biomimetic materials for their unique properties such as high water content, ease of functionalisation, and high biocompatibility. This highlight article describes the recent developments of hydrogels, with a large focus on the supramolecular variants, in their application for 3D cell cultures.

Published online 17 June 2016

CH16127Self-Assembly of an Amphiphilic OEG-Linked Glutamide Lipid

Shuo Wang, Youguo Zhang, Qiang Li, Rongqin Sun, Lin Ma and Liangchun Li
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Amphiphilic peptides with or without oligoethylene glycol (OEG) chains based on 3,4-bis(benzyloxy)benzoic-linked glutamide were designed and their self-assembly was investigated. The studies showed that the amphiphilic peptide 3 with OEG chains could not only form stable gels in a wide range of solvents, but also allowed control of the width of nanofibres in the gel formed with changing water content.

Published online 14 June 2016

CH16126Direct Synthesis of Nitriles from Aldehydes and Hydroxylamine Hydrochloride Catalyzed by a HAP@AEPH2-SO3H Nanocatalyst

Samane Memar Masjed, Batool Akhlaghinia, Monireh Zarghani and Nasrin Razavi
Graphical Abstract Image

We describe an efficient method for the direct preparation of nitriles from aldehydes and hydroxylamine hydrochloride catalyzed by sulfonated nanohydroxyapatite functionalized by 2-aminoethyl dihydrogen phosphate (HAP@AEPH2-SO3H) as an eco-friendly and recyclable solid acid nanocatalyst.

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