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

Australian Journal of Chemistry

Volume 68 Number 5 2015

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In recent years, hypervalent iodine reagents have emerged as powerful tools in synthesis. This highlight paper describes recent developments in the application of diaryliodonium salts for a variety of transformations. It is shown how the extremely electrophilic nature of these reagents can be exploited to difunctionalize alkynes in cascade reactions to access complex scaffolds.

CH14484Ligand Constraints and Synthesis of Metal–Organic Polyhedra

Harsh Vardhan and Francis Verpoort
pp. 707-730
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This review highlights the intercession of ligand constraints and the role of various concepts such as molecular panelling and subcomponent self-assembly in the synthesis of metal–organic polyhedra. This includes discrete architectures of various geometries having an internal cavity of appropriate size and nature suitable enough for a range of applications.

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The synthesis of bis-N-(2,5-dimethoxyphenyl)pyridine-2,6-dicarbothioamide, 6-(4,7-dimethoxy-2-benzothiazolyl)-N-(2,5-dimethoxyphenyl)-2-pyridinecarbothioamide, and the pincer palladium(ii) chloride, and acetate coordination compounds of the latter species are reported. The electrochemical properties, stability constants for the palladium complex formations, the kinetics of formation and the associated thermodynamic parameters are also presented, and the efficacy of the pincer system in the Suzuki–Miyaura cross-coupling reaction is explored.

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We present new ligands N-[3-(3,5-dimethyl-1H-pyrazol-1-yl)propylidene]ethylamine (L1) and N-[3-(3,5-dimethyl-1H-pyrazol-1-yl)propylidene]propylamine (L2) and their reactivity towards ZnII. Complete characterisation of compounds [ZnCl2(L)] (L = L1 (1) and L2 (2)) by analytical and spectroscopic methods and the resolution of structures by single X-ray diffraction are presented. The three-dimensional supramolecular structure through different intra- and intermolecular contacts is also studied.

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The mixed-ligand strategy involving 1,2-phenylenediacetic acid and various nitrogen-rich co-ligands produce three new Zn coordination polymers, which display a vast diversity of structures from two-dimensional (2D) stepwise grids, 2D double layers to three-dimensional (3D)→3D 4-fold interpenetrating diamondoid networks and various ligand-based fluorescence emissions.

CH14441Solvatomorphism and Electronic Communication in FeIII N,N-Bis(salicylidene)-1,3-propanediamine Dimers

Jitnapa Sirirak, David J. Harding, Phimphaka Harding, Lujia Liu and Shane G. Telfer
pp. 766-773
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Two solvatomorphs of [(salpn)Fe(μ2-salpn)Fe(salpn)]·nMeOH (H2salpn = N,N′-bis(salicylidene)-1,3-propanediamine, n = 0.5MeOH (1) and MeOH (2)) are prepared. Structural analysis reveals different packing motifs in the structures resulting in an increased number of layers in 1. Electrochemical studies unexpectedly show weak electronic communication between the FeIII centres in these dimers.

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A series of nanocomposites Ag/ZnO were prepared under different microwave power irradiation which combined with sedimentation, of which ZnO precursor particles were assembled as the characteristic of the cubic lattice of metallic silver. The different microwave power irradiation has an effect on the shapes, physical chemistry properties, and photocatalytic activities of Ag/ZnO.

CH14312Investigation of the Rotational Isomerism of Quinapril and Quinaprilat by UPLC–DAD and Elucidation of the Conformational Equilibrium by NMR

Maha Dendeni, Nicolas Cimetiere, Isabelle Soutrel, Jean Paul Guegan, Najib Ben Hamida and Abdeltif Amrane
pp. 783-792
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Quinapril and quinaprilat are two angiotensin-converting enzyme inhibitors characterized by a band broadening and a peak splitting when analyzed by ultra-performance liquid chromatography. These observations, attributed to the existence of a conformational s-ciss-trans equilibrium, established by the rotation around the peptide bond of both products, were examined by NMR and ultra-performance liquid chromatography–diode array detector.

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Electrochemiluminescence detection and solid phase microextraction using a NH2–graphene–Nafion modified glassy carbon electrode was developed for carbaryl with a linearity range of 5 × 10–4 to 10 μg mL–1 and a detection limit of 2 × 10–4 μg mL–1, which shows good reproducibility, stability, and precision.

CH14393Square-Wave Voltammetric Determination of Nanomolar Levels of Linuron in Environmental Water Samples Using a Glassy Carbon Electrode Modified with Platinum Nanoparticles within a Dihexadecyl Phosphate Film

Paola D. Marreto, Aline B. Trench, Fernando C. Vicentini, Luiz C. S. Figueiredo-Filho, Roberta A. Medeiros, Ernesto. C. Pereira and Orlando Fatibello-Filho
pp. 800-805
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A new sensitive method for linuron determination using a glassy carbon electrode modified with platinum nanoparticles within a dihexadecyl phosphate film (PtNPs-DHP/GCE) and square-wave voltammetry was proposed.

CH14350Cationic Charged Polymer Vesicles from Amphiphilic PEI-g-PSSA-g-PEI as Potential Gene Delivery Vehicles

Liandong Feng, Xinyu Hu, Aming Xie, Hao Yu, Yangyang Liu, Jianfa Zhang and Wei Dong
pp. 806-813
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Polymer vesicles have attracted extensive interest for a variety of biomedical applications. To our knowledge, few reports focus on polymer vesicles for gene delivery. A novel library of cationic polymer vesicles with tunable hydrophobicity is evaluated as efficient and low-cytotoxicity gene vectors.

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An improved route to 2-substituted 6-hydroxy-[3H]-pyrimidin-4-ones and 4,6-dichloropyrimidines using phosphoryl chloride gives yields up to 86 % on a one mol scale. Computations suggest that the chlorination occurs in an alternating phosphorylation–chlorination manner. The investigated 4,6-dichloropyrimidines form strong complexes with dichlorophosphoric acid but weak complexes with hydrochloric acid.

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The novel task-specific ionic liquids (TSILs) introducing piperazine substructures were synthesized via a simple four-step process starting from available materials. TSILs can efficiently remove Cu2+, Ni2+, and Co2+ from water in mild acid solutions. The thermodynamics indicated that the extraction process was exothermic and spontaneous in nature.

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Two novel tri-cholesteryl derivatives gel several liquids at room temperature. One of the gels, 1/cyclohexane, possesses multi-stimuli responsive properties and shows super smart and reversible thixotropic property. These findings suggest that there is a big potential for developing tri-cholesteryl derivatives into extraordinary low molecular mass gelators.

CH14659An Efficient Microwave Method for the Synthesis of Imines

Emily C. Border, Victoria L. Blair and Philip C. Andrews
pp. 844-848
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An efficient microwave synthesis of imines has been developed giving quantitative conversions, in a significantly reduced time frame and without the aid of expensive or elaborate chemicals. A large library of functionalised and unfunctionalised imines was quickly synthesised with minimal workup procedures.

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Professor Kenneth Seddon OBE, one of AJC’s longest-standing Editors, sadly passed away on 21 January from prostate cancer. Ken was one of the world's best ionic liquids experts. His consistent unwavering support, loyalty and advocacy for AJC over the last 10 years will be sorely missed.