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 9 2016

RESEARCH FRONT: Seventh Asia-Pacific Conference of Theoretical and Computational Chemistry (APCTCC7)

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The Seventh Asia-Pacific Conference of Theoretical and Computational Chemistry (APCTCC7) was held in Kaohsiung, Taiwan, from 25 to 28 January 2016. The papers in this Research Front showcase the latest research in theoretical and computational chemistry, including cutting edge applications in drug discovery, materials science, sustainable resources, and nanotechnology.

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This work uses high-level thermochemical procedures to investigate the reaction mechanism for the conversion of important pyrolysis intermediates into levoglucosenone. This process is of importance in biomass conversion. We consider both the uncatalyzed and water-catalyzed reaction mechanisms. We find that a water catalyst leads to a significant reduction in the reaction barrier height for the entire process and to a change in the reaction mechanism.

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The asymptotic functional form preservation method is developed in the framework of supersymmetric quantum mechanics to obtain the energies and wave functions of anharmonic oscillators. Several ansatz functional forms are proposed for the superpotential to obtain the ground and excited state energies with high accuracy.

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The electronic and optical properties of the narrowest armchair graphene nanoribbons (NAGNRs) are studied by various density functional methods. While NAGNRs are found to have stable singlet ground states, the lowest triplet states and the ground states of the cations and anions of NAGNRs exhibit some multi-reference character.

CH16208Guest–Host Interaction of Coinage Metals in π-Rich Cavities

Zhi Xiang Wong and Matthias Lein
pp. 969-974
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It is demonstrated that the reason for the peripheral bonding mode of the coinage metal atoms with [2.2.2]paracyclophane and deltaphane is not an increase of steric repulsion on the inside of the molecular cavity, but rather the decrease of the electrostatic and orbital contributions to the bonding and that the interaction between the cyclophanes and coinage metal cations is non-covalent.

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Salient chemical applications of the recently proposed Atoms in Molecules (AIM) concept based on molecular electrostatic potential (MESP) have been explored. The present work clearly demonstrates the connection of MESP-based AIM with reactivity as well as shielding and deshielding of atoms in NMR studies.

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The catalytic mechanism and origin of stereoselectivity of pentanidium-catalyzed asymmetric phase-transfer conjugate addition were studied by DFT calculations. A docking approach was used to sample the conformational space of the diastereomeric C–C bond-forming transition states. The calculated enantioselectivity is in excellent accord with experiment result.

CH16248Energetics of the Proton Transfer Pathway for Tyrosine D in Photosystem II

Keisuke Saito, Naoki Sakashita and Hiroshi Ishikita
pp. 991-998
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The proton transfer pathway for redox active tyrosine D (TyrD) in photosystem II is a hydrogen-bond network that involves D2-Arg180 and a series of water molecules. The potential-energy profile of all hydrogen bonds along the proton transfer pathway indicates that the overall proton transfer from TyrD is energetically downhill.

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We present a simple yet systematic way to investigate the degree of electron delocalization and structural heterogeneity of cyclic conjugated molecules based on molecular dynamics simulations. π-Electron delocalization is strongly correlated with the planarity of the system. Torsional angle and out-of-plane distance distributions were calculated for the degree of electron delocalization.

CH16232An In Silico Approach of Coumarin-Derived Inhibitors for Human DNA Topoisomerase I

Amali G. Guruge, Chandani Udawatte and Samantha Weerasinghe
pp. 1005-1015
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Human DNA topoisomerase I (Htopo I) is a validated target for anti-cancer agents; however, available anti-cancer agents are linked with several limitations. Therefore, discovering novel inhibitors for Htopo I is essential. Recent studies have demonstrated that coumarins exhibit anti-cancer activity against several targets. Thus, the current study focussed on predicting coumarin-derived inhibitors as lead compounds for further drug design.

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Five thiosemicarbazone ligands have been synthesized and their coordination chemistry with gallium investigated. All compounds have been fully characterized by NMR and X-ray crystal structures of two of the complexes are reported. Additionally, the positron emitting isotope 18F was introduced in the structure of the diphenyl gallium thiosemicarbazone complex using a halogen exchange method.

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A multicomponent reaction capable of affording a wide range of novel 7,11-dihydro-6H-chromeno[3,4-e]isoxazolo[5,4-b]pyridin-6-one derivatives via one-pot three-component condensation of 4-hydroxycoumarin, aromatic aldehydes, and 5-amino-3-methylisoxazole in ionic liquid [C4mim][HSO4] is reported.

CH15794The Influence of Amino Group Position on Aryl Moiety of SarAr on Metal Complexation and Protein Labelling

Vincent Jamier, Eskender Mume, Cyril Papamicaël and Suzanne. V. Smith
pp. 1054-1061
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New hexaazamacrobicyclic cage bi-functional chelators (BFCs), 1-N-(3-aminobenzyl)-3,6,10,13,16,19-hexaazabicyclo[6.6.6]eicosane-1,8-diamine (m-SarAr) and 1-N-(2-aminobenzyl)-3,6,10,13,16,19-hexaazabicyclo[6.6.6]eicosane-1,8-diamine (o-SarAr), were synthesised and their metal complexation and conjugation to proteins were compared with p-SarAr.

Current Issue

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

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 28 April 2016

CH16021Double-Headed Nucleotides: Building Blocks for New Nucleic Acid Architectures

Pawan K. Sharma, Pawan Kumar and Poul Nielsen
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Double-headed nucleotides are designed for using the recognition potential of the additional nucleobases in various nucleic acid constructs. Presented here is a review of the double-headed nucleotide monomers investigated so far and their effects in nucleic acid duplexes and other secondary structures.

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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 07 June 2016

CH16102Novel Thymohydroquinone Derivatives as Potential Anticancer Agents: Design, Synthesis, and Biological Screening

Ahmed H. Abdelazeem, Yasser M. A. Mohamed, Ahmed M. Gouda, Hany A. Omar and Majed M. Al Robaian
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Three series of THQ-based derivatives were synthesised and evaluated for their anticancer activity against a panel of cancer cell lines. Initial screening revealed that compounds 5d and 6 exerted better activity against MCF-7 than TQ, with IC50 values of 9.6 and 10.0 μM, respectively. These compounds were able to elicit apoptotic cell death through activation of caspase 3/7.

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Two new complexes based on 5-nitroisophthalic acid (NIPH) and bis(imidazol) ligands (bimb, mbix), namely, [Co(NIPH)(bimb)(H2O)]n (1) [Ni(NIPH)(mbix)]n (2), have been successfully synthesised under hydrothermal conditions.

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 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.

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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.

Published online 07 April 2016

CH16020Therapeutic Potential of miR-494 in Thrombosis and Other Diseases: A Review

Jasmine Tay, Jim Tiao, Quintin Hughes, Grace Gilmore and Ross Baker
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Many studies have identified the microRNA, miR-494, as a regulator of many cellular processes, and we have demonstrated the role of miR-494 in regulating thrombosis via direct targeting of the anticoagulant factor, Protein S. Changes in miR-494 levels have been reported to be detectable in various biological fluids, thus making miR-494 a good diagnostic marker and therapeutic target.

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

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Herein, we present the use of tert-butyldimethylsilyl amine (TBDMS-NH2) as a silylating reagent for phenols, benzyl alcohols, and carboxylic acids under solvent-free conditions. Interestingly, this process is rapid and does not involve the formation of HCl unlike other protection processes.

Published online 01 June 2016

CH16144Polyanhydrides: Synthesis, Properties, and Applications

Katie L. Poetz and Devon A. Shipp
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Polyanhydrides are a fascinating class of degradable polymers that have application in drug delivery, stimuli-responsive materials, and novel nanotechnologies because of their degradability and capacity to undergo surface erosion. This review examines approaches for polyanhydride synthesis, thermomechanical properties, biocompatibility, and hydrolysis and degradation processes.

Published online 24 August 2016

CH16211E-Cadherin Aptamer-Conjugated Delivery of Doxorubicin for Targeted Inhibition of Prostate Cancer Cells

Resham Chaudhary, Kislay Roy, Rupinder K. Kanwar, Rakesh N. Veedu, Subramanian Krishnakumar, Chun Hei Antonio Cheung, Anita K. Verma and Jagat R. Kanwar
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Doxorubicin (Dox) is a substrate of drug resistance marker P-glycoprotein (P-gp) and, therefore, on entry is effluxed out of cells via P-gp activity. The E-cadherin aptamer–doxorubicin conjugate (Ecad01-Dox) can enter the cell directly as well as by receptor (E-cadherin)-mediated internalization, leading to increased intracellular uptake of Dox.

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An efficient, mild, and environmental friendly method has been developed for the synthesis of dihydropyrano[2,3-c]pyrazole over TBD-MSN catalyst by assembling ethyl acetoacetate, hydrazine hydrate, different aldehydes, and malononitrile affording the product in excellent yields. The catalyst was reused several times with retention of activity.

Published online 30 May 2016

CH16169Substituted Carbazoles – A New Class of Anthelmintic Agent

David Rennison, Stephanie M. Gueret, Olivia Laita, Ross J. Bland, Ian A. Sutherland, Ian K. Boddy and Margaret A. Brimble
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A series of novel carbazoles were synthesized based on structural modifications to lead carbazole 1; several analogues were subsequently demonstrated to exhibit anthelmintic activity both in vitro (H. contortus) and in vivo (H. polygyrus).

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Palladium(ii) complexes with N-benzyliminodiacetic acid derivatives, RN(CH2COOH)2 (RidaH2; R = benzyl, para-chlorobenzyl, para-nitrobenzyl, or para-methoxybenzyl), were prepared and characterized by infrared spectroscopy and thermal analysis. Two types of complexes, dihydrates [Pd(RidaH)2]·2H2O and anhydrous complexes [Pd(RidaH)2], were successfully distinguished on the basis of their infrared spectra with the aid of density function theory calculations at the BP86/6–311+G(d,p) level of theory with SDD pseudopotentials.

Published online 10 June 2016

CH16132Backbone Phosphonamide-Functionalized Imidazol-2-ylidene Complexes

Paresh Kumar Majhi, Gregor Schnakenburg, Anthony J. Arduengo and Rainer Streubel
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The synthesis of metal (Cr, Mo, Rh, Au) complexes bearing 4-phosphonamide and 4,5-bis(phosphonamide)-imidazol-2-ylidene ligands (NHCP) is reported. Phosphonamidyl NHC ligands are generated by deprotonation of imidazolium salts or imidazolium-based ionic liquids.

Published online 17 May 2016

CH16073Hydrolysis of Queensland fruit fly, Bactrocera tryoni (Froggatt), attractants: kinetics and implications for biological activity

Soo J. Park, Matthew S. Siderhurst, Ian Jamie and Phillip W. Taylor
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The kinetics of hydrolysis of the most commonly used attractant, cuelure (CL), for Queensland fruit fly, Bactrocera tryoni (Froggatt), and two closely related compounds, melolure (ML) and a newly developed lure, 4-(4-(2,2,2-trifluoroacetoxy)phenyl)-2-butanone (RKTA), were quantitatively investigated by GC-FID.

Published online 17 May 2016

CH16064Ultrasonic Synthesis and Properties of Sodium Lignosulfonate-grafted Poly(Acrylic Acid-co-Vinyl Alcohol) Composite Superabsorbent Polymer

Chen Hao, Jun Li, Qiang He, Zilong Zhou, Xiaowei Guo, Xiaohong Wang, Sijia Gao and Yike Zhang
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Under the initiation of ammonium persulfate, acrylic acid was successfully grafted onto the polyvinyl alcohol and sodium lignosulfonate in the reaction system with the assistance of ultrasound, and then an environmental friendly and biodegradable superabsorbent with semi-interpenetrating networks structure was formed due to the binding effect of N,N′-dimethyl acrylamide.

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
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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.

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 20 May 2016

CH16119Highly Ordered Honeycomb Film Formation of Linear Polymers by the Breath Figure Technique

Paul A. Gurr, Zhou Zhang, Xiaojuan Hao, Timothy C. Hughes and Greg G. Qiao
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The incorporation of a simple fluorinated polymer additive in small amounts facilitated the formation of regular honeycomb (HC) films from polymers. Typically highly ordered HC films are difficult to form from such polymers. From analysis of the properties of these mixtures, a new hypothesis was developed, which will provide a new tool to guide and allow the use of a broader range of polymers to prepare HC films.

Published online 24 May 2016

CH16189Template Polymerization of Acrylamide in Ethanol/Water Mixtures

Jie Dong, Xiang'an Yue and Jie He
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Irregular hollow polyacrylamide (PAAm) particles were prepared in ethanol/water mixtures by template polymerization of acrylamide using polyvinyl butyral (PVB) as the template material and 2,2′-azobisisobutyronitrile (AIBN) as the initiator. It was found that the shrinkage and dehydration on hollow PAAm particles results in the formation of micro-sized irregular hollow PAAm particles.

Published online 23 March 2016

CH15743Practical Isolation of Asperuloside from Coprosma quadrifida via Rapid Pressurised Hot Water Extraction

Bianca J. Deans, Alex C. Bissember and Jason A. Smith
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Multigram quantities of asperuloside, a glycoside natural product, have been isolated from Coprosma quadrifida in a time-efficient and practical manner via rapid pressurised hot water extraction employing an unmodified household espresso machine. By this approach one of the highest yields of asperuloside from a plant species was obtained.

Published online 01 July 2016

CH16151A New Technique for Studying Vapour–liquid Equilibria of Multi-Component Systems

Federico M. Ferrero Vallana, Lynette A. M. Holland and Kenneth R. Seddon
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A new Fourier transform infrared gas-phase method for measuring the vapour pressure of each component of a poorly volatile mixture, and determining the vapour phase composition for each system, is described. The method has been validated using two standards, and a Raoult’s plot surface of a ternary system is reported as proof-of-principle.

Published online 20 July 2016

CH16296Spotlight on Varietal Thiols and Precursors in Grapes and Wines

David W. Jeffery
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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.

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.

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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.

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 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 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 24 June 2016

CH16072Electrochemical Investigation of Gold Nanoparticle-Modified Glassy Carbon Electrode and its Application in Ketoconazole Determination

Mutasem M. Alshalalfeh, Manzar Sohail, Tawfik A. Saleh and Md. Abdul Aziz
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Ketoconazole (KCZ) is an antifungal compound and an active ingredient of anti-scaling shampoos and skin ointments. In this work, the cyclic voltammetric behaviour of KCZ was studied with a gold nanoparticle (AuNP)-modified glassy carbon (GC) electrode.

Published online 13 July 2016

CH16272Non-Equilibrium Capillary Electrophoresis of Equilibrium Mixtures-Based Affinity Separation and Selective Enrichment of a Long-Length DNA Aptamer

Kenta Hagiwara, Yuuya Kasahara, Hiroto Fujita and Masayasu Kuwahara
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Peak separation of a long-length DNA aptamer complexed with its target via non-equilibrium capillary electrophoresis of equilibrium mixtures (NECEEM) and its enrichment through selection process cycles have been demonstrated.

Published online 05 August 2016

CH16369Crystal Structures of the Amide and Iminol Tautomers O-(3,5-dinitrobenzoyloxy)benzohydroxamate. A case of a disappearing solvate?

Abigail L. Albright, Lucy Collins, John Li, Benjamin Harris and Jonathan M. White
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O-(3,5-dinitrobenzoyloxy)benzohydroxamate crystallizes as its imino tautomer in the presence of dimethyl sulfoxide and its amide tautomer in the absence of dimethyl sulfoxide.

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 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.

Published online 04 July 2016

CH16050Kinetics and Mechanism of Oxidation of d-Penicillamine in Acidified Bromate and Aqueous Bromine

Kudzanai Chipiso and Reuben H. Simoyi
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Oxidation of the biologically active compound d-penicillamine (Depen) by acidic bromate has been studied. It is oxidized as far as its sulfonic acid. ESI spectroscopy shows that Depen is oxidized through addition of oxygen atoms on the sulfur centre to successively yield sulfenic and sulfinic acids before the product sulfonic acid.

Published online 04 July 2016

CH16176A Colorimetric Approach towards Polycyclic Aromatic Hydrocarbon Sensing

Walmiria Woodland, Cherie A. Motti, Paul Irving, Lynne Van Herwerden and George Vamvounis
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The colorimetric sensing of polycyclic aromatic hydrocarbons (PAHs) was achieved using a photochromic compound. This detection technology was highly sensitive (by absorbing UV radiation) and selective (using different excitation wavelengths). PAH mixtures were successfully identified, allowing fast in-field identification of spilled oil sources.

Published online 14 June 2016

CH16074Hydrophilic Magnetite Nanoparticles Enhance Anticancer Activity of Anthracyclines In Vitro

Bin Yang, Lin Luo, Ying Ma, Chunyan Chen, Xiaoming Chen and Changqun Cai
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Citric acid-coated magnetite nanoparticles Fe3O4 (nano-Fe3O4-CA) interacted with anthracyclines, and the aggregates (nano-Fe3O4-CA-drug) formed. Further studies indicated that the interactions between them were electrostatic and hydrophobic forces. Additionally, the cytotoxicity of nano-Fe3O4-CA-drug was investigated by cytotoxicity experiment and cell morphology study, which indicated that the nano-Fe3O4-CA-drug has a lower cytotoxicity than anthracyclines.

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.

Published online 05 September 2016

CH16428Masked Ketenes as Dienophiles in the Diels–Alder Reaction

Emily G. Mackay and Christopher G. Newton
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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.

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 06 June 2016

CH16022Development of Lignocellulosic Biorefinery Technologies: Recent Advances and Current Challenges

Antonella Amore, Peter N. Ciesielski, Chien-Yuan Lin, Davinia Salvachúa and Violeta Sànchez i Nogué
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Biomass deconstruction and conversion of sugar and lignin to high-value products are the essential steps in the implementation of next-generation lignocellulosic biorefineries. Understanding the interplay between conversion processes and the structure of lignocellulosic feedstocks is a critical point, warranting the development of feedstock engineering techniques and advanced characterization methods, in tandem with the deployment of tailored deconstruction and upgrading processes.

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 21 September 2016

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
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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.

Published online 03 May 2016

CH16100Prodrug Micelles Based on Norbornene-Functional Poly(lactide)s Backbone for Redox-Responsive Release of Paclitaxel

Ji Wang, Jing Yan, Huicong Zhou, Haikang Huang, Xuefei Zhang and Haoyu Tang
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A novel norbornene-functional poly(lactide)s backbone-based redox-responsive prodrug, P(LA-g-mOEG)-b-P(LA-SS-PTX), was successfully synthesized by combination of ring-opening polymerization, click, ester, and condensation reactions. The self-assembled micelles formed from paclitaxel prodrugs displayed a spherical shape with appropriate sizes for enhanced permeability and retention effect and a narrow size distribution. With disulfide linkages, prodrug micells showed redox-responsive drug release behaviours in response to the intracellular level of reducing potential.

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Two barium(ii) 2D coordination polymers, {[Ba(µ-H2O)(H2O)2(µ-pyzdc)]}n (1) and {[Ba(H2O)2(µ-Hpyzdc)(Hpyzdc)]2H2O}n (2) (pyzdcH2 = pyrazine-2,3-dicarboxylic acid), were prepared by reaction of barium(ii) chloride dihydrate and pyzdcH2 under slightly different pH values. The barium(ii) ion has distorted bicapped square antiprismatic coordination geometry in 1 and distorted tricapped trigonal prismatic geometry in 2.

Published online 09 May 2016

CH16079Preclinical Imaging of siRNA Delivery

Nicholas Fletcher, Aditya Ardana and Kristofer J. Thurecht
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Small interfering RNA (siRNA) is a class of therapeutic with extremely high potential. However, further understanding of how siRNA behaves in vivo is still required before significant uptake into clinical application. To this end, molecular imaging has been utilised to gain a better understanding of administered siRNA and delivery vehicle biodistribution and pharmacokinetics.

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 25 May 2016

CH16060The Effects of SiO2 and CeO2 Addition on the Performances of MnOx/TiO2 Catalysts

Juhua Luo, Hongkai Mao, Xu Wang and Wei Yao
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MnOx-CeO2/TiO2-SiO2 were prepared by an impregnation method and their selective catalytic reduction of NO with NH3 at low temperature was evaluated. NO conversion of the MnOx/TiO2-SiO2 catalyst could be improved by the addition of CeO2 in the temperature range of 100–180°C. MnOx-CeO2/TiO2-SiO2 with 10 wt-% CeO2 showed the highest activity with 96 % NO conversion at 180°C.

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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 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 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.

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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.

Published online 29 April 2016

CH16067Loading of a Phenanthroline-Based Platinum(ii) Complex onto the Surface of a Carbon Nanotube via π–π Stacking

Stephanie A. Houston, Natarajan S. Venkataramanan, Ambigapathy Suvitha and Nial J. Wheate
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The anticancer metal complex [(1,10-phenanthroline)(1S,2S-diaminocyclohexane)platinum(ii)]2+ forms a supramolecular complex with multi-walled carbon nanotubes through π–π stacking.

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An orthogonal molecular interaction (OMI) system between a native hydrogen bond (H-bond) and a constructed halogen bond (X-bond) across the complex interface of oncogenic protein MDM2 with the p53 peptide was designed computationally. Fluorescence polarization assays revealed that the designed OMI system can considerably improve peptide binding affinity to MDM2.

Published online 02 September 2016

CH16451Substance Abuse: Carbon Tetrachloride and the Ozone Layer

Ian D. Rae
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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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RAFT Compilation

The publication rate on RAFT polymerization continues to increase with the publication of a third update.
Freely access the three reviews previously written by CSIRO scientists Moad, Rizzardo, and Thang on this subject in Australian Journal of Chemistry.