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 70 Number 12 2017

CH17168Alkali Metal Ion-Exchanged Zeolite X from Bamboo Leaf Biomass as Base Catalysts in Cyanoethylation of Methanol Enhanced by Non-Microwave Instant Heating

Eng-Poh Ng, Jack-Hao Chow, Siew-Fang Wong, Rino R. Mukti, Oki Muraza, Tau Chuan Ling and Ka-Lun Wong
pp. 1239-1246
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Zeolite X base catalysts containing alkali metal ions are prepared from amorphous bamboo leaf ash. The catalysts are found to be highly active in cyanoethylation of methanol under an instant heating environment that mimics microwave fast heating.

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Secondary amines react with maleic anhydride under kinetic control across the C=O functionality exclusively. The product changes into N-substituted maleimic acid under thermodynamic control. The Fukui functions determined at the B3LYP/6-31G* level reveal that the carbon atom of the carbonyl group is the hardest site, thus making it the preferred site for the nucleophilic attack.

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New azomethine receptors were designed and synthesised for rapid and naked eye detection of inorganic fluoride anions in semi-aqueous media. The sensing ability of the receptors towards F has been investigated spectroscopically. By using F and H+ as chemical inputs and the absorbance as output, an INHIBIT logic gate was constructed, which exhibits ‘Write–Read–Erase–Read’ ability without obvious degradation in its optical output.

CH17220Recognition of a Flavin Analogue by Novel Bile Acid-Based Receptors: Effects of Hydrogen Bonding and Aromatic π-Stacking Interactions

Pradeep Kumar Muwal, Rajesh Kumar Chhatra, Shubhajit Das and Pramod S. Pandey
pp. 1263-1268
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Synthesis and binding behaviour of bile acid-based flavin receptors containing 2,6-diaminopyridine and aromatic moieties are reported. These receptors display significant influence of steric and aromatic π-stacking interactions, along with hydrogen bonding, on their binding with N-(10)-hexylflavin derivative.

CH17270Synthesis and Crystal Structure of Unexpected (1S,4R,5R,6S)-4-Cyano-2,2,6-trimethyl-3-azabicyclo[3.3.1]nonan-6-yl Acetate

Steven Gareth Williams, Mohan Bhadbhade, Roger Bishop and Alison Thavary Ung
pp. 1269-1273
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A novel alkaloid-like compound containing the azabicyclo[3.3.1]nonane core is reported to be the first instance of using the bridged Ritter reaction with hydrogen cyanide. The structure of this unique and unexpected compound was determined with the aid of X-ray crystallography.

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A novel, simple and straightforward combinatorial method for the synthesis of new substituted 3-(arylamino)-6,7-dihydro-1H-indazol-4(5H)-one derivatives has been developed. The synthesis was achieved via a one-pot three-component reaction of aromatic isothiocyanates, substituted 1,3-cyclohexanediones, and hydrazine hydrate in dimethyl sulfoxide.

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Novel 1,3-oxazine hybrids of sesamol and quinoline have been synthesized via one-pot reaction of sesamol/6-hydroxyquinoline, aromatic amines, and formaldehyde. The structures of all the novel compounds were confirmed by spectral data. The structure of the synthesized hybrids was also confirmed by X-ray crystallographic studies.

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Star-shaped block copolymers based on poly(N-vinylcaprolactam) and functionalized with polyethylene glycol have been synthesized. The star-shaped block copolymers self-assemble spontaneously into aggregates in water and were used to encapsulate methotrexate.

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A prodrug mPEG-b-PCL-(g-PTX)-b-PLA-(g-LA) has been synthesized, which may exchange ligands with QDs to form a nanotheranostic system (prodrug-co-QDs). This novel system exhibited good controlled drug release behaviour due to the ester linkage between the drug and polymer. By using typical cancer cell lines, we showed that this nanotheranostic system is promising in cancer diagnosis and treatment in vitro.

CH17456Effect of Structured Surfaces on MALDI Analyte Peak Intensities

Sajid Bashir, Jingbo L. Liu and Peter J. Derrick
pp. 1312-1316
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A surface modification method is presented where sodium chloride crystal was deposited onto a stainless steel surface. The surface was subjected to various stimuli to induce surface defects either on the surface or crystal and the ion yield of substance P was investigated as a function of stimuli. The interaction of the laser resulted in an increase in the ion yield of substance P (3–17 fold increase relative to no stimuli).

CH174761,3-Dipolar Cycloaddition of a Nitronyl Nitroxide-Substituted Alkyne to Heteroaromatic N-Imines

Vasiliy Romanov, Aleksey Vorob'ev, Irina Bagryanskaya, Dmitriy Parkhomenko and Evgeny Tretyakov
pp. 1317-1320
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We report on the 1,3-dipolar cycloaddition of the triple bond in an ethynyl-substituted nitronyl nitroxide to heteroaromatic N-imines. The reaction opens a new pathway to polyfunctional nitronyl nitroxides with pyrazolo[1,5-a]pyridine or related substituents that are in demand in coordination chemistry and molecular magnetism fields.

Online Early

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

Published online 08 December 2017

CH17420Superoxide Anion Biosensor Based on Bionic-Enzyme Hyperbranched Polyester Particles

Yanlian Niu, Sisheng Hu, Qian Zhou, Yang Liu, Yuhong Liu, Jing Zhao, Mimi Wan, Wenbo Zhao and Jian Shen
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Conventionally synthesised Mn-superoxide dismutase mimics have a multilayer sheet structure with uncontrolled shape, which wastes resources and has a low catalytic efficiency. Here, a bionic-enzyme hyperbranched polyester (HBPE-AMPA-Mn2+) has been synthesised by a self-assembly technique. Results indicate that an electrochemical biosensor based on HBPE-AMPA-Mn2+ particles has excellent electrochemical performance.

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DMT ((–)-(2R,3R)-2,3-dimethoxy-1,1,4,4-tetraphenylbutane-1,4-diol) is an efficient host compound for guests aniline, N-methylaniline, and N,N-dimethylaniline. This host displays high selectivity for N,N-dimethylaniline when recrystallized from various mixtures comprising these three guests. DMT may therefore have future application in the separation of these anilines.

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Ingenol-3-angelate is a potent anticancer compound. This work uses double-hybrid density functional theory to investigate the reaction mechanisms (uncatalysed and water-catalysed) for acyl rearrangements in this compound. These rearrangements may affect the potency of the drug and its shelf-life. We find that a water catalyst leads to a significant reduction in the reaction barrier heights for the acyl migrations.

Published online 22 November 2017

CH17406Phosphate and Phosphonate-Based Ionic Liquids as New Additives in Foeniculum vulgare Essential Oil Extraction

Luisa Pistelli, Rose Vanessa Bandeira Reidel, Piero Margari and Cinzia Chiappe
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Four ionic liquids (ILs) were added separately in the essential oil extraction of Foeniculum vulgare fruits. The use of each aqueous solution of IL afforded an increase in the essential oil yield. There is possibility of reuse of the IL solutions and no variation in the fennel essential oil composition was evidenced.

Published online 22 November 2017

CH17492Fluorogens: Generating Receptor-Specific Turn-On Fluorescence

Joshua W. Conner
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Fluorogens are new generation small molecule organic dyes that offer an alternative, rapid, and non-covalent labelling strategy. These otherwise dark molecules bind to genetically encoded recognition domains, termed fluorogen activating proteins (FAPs), causing a protein-mediated constraint of rotation of a single bond within the fluorogens, and leading to increased fluorescence as high as 20000-fold.

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Self-assembled nanoparticles, or nanoassemblies, of paramagnetic amphiphilic chelates have high potential as magnetic resonance imaging (MRI) contrast agents. However, due to the inherently large paramagnetic chelate as the head group (CPP <1), it is challenging to design paramagnetic amphiphiles to confer nanoassemblies with highly ordered interior nanostructures. Recent studies reporting stable, highly ordered nanoassemblies of paramagnetic amphiphilic chelates are presented here.

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Quantum-chemical calculations were performed on the so far elusive compounds inda- and thallabenzene. The ground states of both compounds were found to be triplets with the lowest closed-shell singlets up to 3 kcal mol−1 higher in energy. The η5 isomers were found to be energetically up to 102 kcal mol−1 below the six-membered rings.

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Introduction of the 1,3,5-benzenetricarboxylate into the zinc-triazolate system gave the 3D porous structure of 1 based on pentanuclear [Zn53-OH)2] clusters and exhibited selective gas adsorption. While a variation of BTC3−, the 5-sulfoisophthalate was introduced into the zinc-triazolate system yielding a non-porous structure of 2 constructed from pentanuclear [Zn5(trz)8] clusters, demonstrating that the secondary ligands play an important role in the formation of the final structures.

Published online 27 October 2017

CH17341Regioselective Synthesis of 2,5-Disubstituted Pyrroles via Stepwise Iododesilylation and Coupling Reactions

Qixin Yu, Xiaoyu Li, Xinyue Wang and Jianhui Liu
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The regioselective preparation of 2,5-disubstituted pyrroles, useful structural scaffolds, is important. To this end, a protocol based on a stepwise iododesilylation and a subsequent coupling reaction, involving a 6-step pathway starting from the simplest pyrrole, has been realised. This methodology can be widely used in the synthesis of drugs, molecular wires, and high-molecular-weight polymers.

Published online 18 October 2017

CH17354Ultrafast NH3 Sensing Properties of WO3@CoWO4 Heterojunction Nanofibres at Room Temperature

Yiming Zhao, Muhammad Ikram, Jianzhou Wang, Zhi Liu, Lijuan Du, Jiao Zhou, Kan Kan, Weijun Zhang, Li Li and Keying Shi
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A Co-W nanofibre sensor was found to exhibit excellent gas-sensing properties at room temperature, such as a response of 1.17 and 3 s to 1000 ppm NH3, and the response time always remained within 5 s for a NH3 concentration range of 1000–10 ppm, due to the single crystal CoWO4–CoWO4 homojunctions and unique massage ball-like WO3–CoWO4 heterojunctions.

Published online 16 October 2017

CH17359First Year Introductory Chemistry at the University of Western Australia: Reflections and Perceptions

Tristan D. Clemons, Robert B. Bucat and Dino Spagnoli
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This study investigated the motivations and attitudes of two student cohorts enrolled in an introductory chemistry unit, which Emeritus Professor Graham Chandler helped to create. An interview with Graham describes the origins of this unit. Therefore, this study has particular interest in this special issue celebrating Graham’s career in chemistry.

Published online 11 October 2017

CH17334A Novel Strategy to Introduce 18F, a Positron Emitting Radionuclide, into a Gallium Nitrate Complex: Synthesis, NMR, X-Ray Crystal Structure, and Preliminary Studies on Radiolabelling with 18F

Taracad K. Venkatachalam, Paul V. Bernhardt, Damion H. R. Stimson, Gregory K. Pierens, Rajiv Bhalla and David C. Reutens
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Substituted diphenyl dithiosemicarbazone gallium nitrate and fluoride complexes have been synthesised and the structures confirmed by NMR and X-ray crystallography. Radiolabelling of the nitrate complexes has been performed with fluorine-18, resulting in the formation of Ga-18F complexes.

Published online 10 October 2017

CH17214An Injectable Oxidized Carboxymethyl Cellulose/Polyacryloyl Hydrazide Hydrogel via Schiff Base Reaction

Xueying Sheng, Xian Li, Mengting Li, Renyi Zhang, Shuang Deng, Wangkai Yang, Guanjun Chang and Xu Ye
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A series of injectable oxi-CMC/PAH hydrogels was prepared via a Schiff base reaction under physiological conditions. The oxi-CMC6/PAH3 hydrogel exhibited good comprehensive properties and in vitro sustained release of BSA, showing that it could be potentially applied in the fields of drug delivery vehicles, tissue engineering, and cell encapsulation materials.

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N,N-Dialkyl-N′-chlorosulfonyl chloroformamidines 1 reacted regioselectively with benzimidazoles bearing an activated methylene group at C2 to afford derivatives of the new benzo[4,5]imidazo[1,2-b][1,2,6]thiadiazine ring system. Substitution reactions of the new system occurred selectively at N5 (not at N2).

Published online 20 September 2017

CH17202Investigation of Hybrid Materials Based on Polyurethane Modified with Aliphatic Side Chains Combined with Nano-TiO2

Jie Zhang, Nanjie Zhang, Quan Liu, Haojun Ren, Pengfei Li and Kang Yang
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Polyurethanes (PUs) were synthesised using methylene diphenyl diisocyanate (MDI), polytetrahydrofuran ether diol (PTMG), and chain extenders containing different amounts of aliphatic side chains. Hybrid materials were then prepared by reacting the PUs with nano-TiO2. The effects of different molecular structures of the chain extenders on the surface properties of PU coatings and the hybrid materials were investigated.

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A series of carbon-based solid acid catalysts derived from biomass was prepared and used for the conversion of fructose to 5-HMF, which is a very important platform chemical due to its unique chemical structure. The results suggest that sulfonated carbon materials exhibit remarkable catalytic capability for fructose dehydration to 5-HMF.

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The co-operative stabilizations associated with the bending of the σC–C toward C–F bonds and total hyperconjugative generalized anomeric effect in the cis-configuration of 1,2-difluoroethene overcome the destabilizations associated with the exchange component and dipole–dipole interactions, leading to the preference of the cis-configuration in the compound.

Published online 14 August 2017

CH17248New Organic Acidic Cyclohexaphosphate: Synthesis, Crystal Structure, Physicochemical Study, and In Vitro Biochemical Investigation

Ramzi Fezai, Lamia Khedhiri, Hanene Hemissi, Ali Mezni and Mohamed Rzaigui
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The present paper reports a new hybrid cyclohexaphosphate which was characterized by different techniques (NMR, IR, UV-vis) and evaluated (electrical and biological). This reported compound exhibits an acidic character which is rarely observed with this type of condensed phosphate. In addition, this material is distinguished from others by its higher thermal stability and more pronounced antioxidant activity.

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