ORCID Profile
0000-0002-6995-9311
Current Organisation
University of New South Wales
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Research Topics
In Research Link Australia (RLA), "Research Topics" refer to ANZSRC FOR and SEO codes. These topics are either sourced from ANZSRC FOR and SEO codes listed in researchers' related grants or generated by a large language model (LLM) based on their publications.
Top 5 Research Topics
ANZSRC Field of Research (FoR)
Chemical Engineering | Catalysis and Mechanisms of Reactions | Catalytic Process Engineering
ANZSRC Socio-Economic Objective (SEO)
Management of Solid Waste from Manufacturing Activities | Organic Industrial Chemicals (excl. Resins, Rubber and Plastics) | Environmentally Sustainable Manufacturing not elsewhere classified |
Related Links
Publications
Why is RCM favoured over dimerisation? Predicting and estimating thermodynamic effective molarities by solution experiments and electronic structure calculations
Publisher: Wiley
Date: 04-10-2011
Abstract: The thermodynamic effective molarities of a series of simple cycloalkenes, synthesised from α,ω-dienes by reaction with Grubbs' second generation precatalyst, have been evaluated. Effective molarities were measured from a series of small scale metathesis reactions and agreed well with empirical predictions derived from the number of rotors and the product ring strain. The use of electronic structure calculations (at the M06-L/6-311G** level of theory) was explored for predicting thermodynamic effective molarities in ring-closing metathesis. However, it was found that it was necessary to apply a correction to DFT-derived free energies to account for the entropic effects of solvation.
Copper(I)-catalysed site-selective C(sp 3)–H bond chlorination of ketones, (E)-enones and alkylbenzenes by dichloramine-T
Publisher: Springer Science and Business Media LLC
Date: 07-2021
DOI: 10.1038/S41467-021-23988-Y
Abstract: Strategies that enable intermolecular site-selective C–H bond functionalisation of organic molecules provide one of the cornerstones of modern chemical synthesis. In chloroalkane synthesis, such methods for intermolecular site-selective aliphatic C–H bond chlorination have, however, remained conspicuously rare. Here, we present a copper(I)-catalysed synthetic method for the efficient site-selective C( sp 3 )–H bond chlorination of ketones, ( E )-enones and alkylbenzenes by dichloramine-T at room temperature. A key feature of the broad substrate scope is tolerance to unsaturation, which would normally pose an immense challenge in chemoselective aliphatic C–H bond functionalisation. By unlocking dichloramine-T’s potential as a chlorine radical atom source, the product site-selectivities achieved are among the most selective in alkane functionalisation and should find widespread utility in chemical synthesis. This is exemplified by the late-stage site-selective modification of a number of natural products and bioactive compounds, and gram-scale preparation and formal synthesis of two drug molecules.
Recent Advances in the Gold-Catalyzed Reactions of Propargyl Esters
Publisher: American Chemical Society (ACS)
Date: 06-06-2023
7-Selenabicyclo[2.2.1]heptane
Publisher: Royal Society of Chemistry (RSC)
Date: 2012
DOI: 10.1039/C2CC34984A
Abstract: Thermolysis of a benzene solution of N-[4-(p-(methoxybenzyl)seleno)cyclohexanoyl]-N,S-dimethyldithiocarbonate affords the hitherto unknown 7-selenabicyclo[2.2.1]heptane in 48% conversion and in 20% yield after chromatography. G3(MP2)-RAD calculations predict a rate constant of 5 × 10(4) s(-1) at 80 °C (3.8 × 10(6) s(-1) at 200 °C) for the intramolecular homolytic substitution process involved in this cyclization.
Ab initio studies of carbonyl radical additions to hydrazone systems
Publisher: CSIRO Publishing
Date: 2009
DOI: 10.1071/CH09165
Abstract: Ab initio and DFT calculations reveal that intermolecular radical additions of both acyl and oxyacyl radials to hydrazones occur through SOMO → π*hydrazone, πhydrazone → SOMO and LPN → SOMO interactions between the radical and the hydrazone π-system. Both acetyl and methoxycarbonyl radicals show preference for addition to the carbon end of the carbon–nitrogen π-bond. At the highest level of theory used in this study (G2//MP2(full)/6-31G*), energy barriers of 11.2 and 22.6 kJ mol–1 are calculated for acetyl radical addition to the carbon and nitrogen-ends of N-aminomethanimine respectively. The analogous energy barriers for the methoxycarbonyl radical are 4.9 and 25.7 kJ mol–1 at the same level of theory.
“Every little thing that could possibly be provided helps”: analysis of online first-year chemistry resources using the universal design for learning framework
Publisher: Royal Society of Chemistry (RSC)
Date: 2022
DOI: 10.1039/D1RP00171J
Abstract: Rapid advancements in information and communication technologies (ICTs) have afforded numerous variations to traditional chemistry curricula where pedagogical strategies that have been employed have assumed “one-size-fits-all”. The translation of print-based instructional resources into multimodal online and digital forms enables greater accessibility, flexibility, and usability to support students in their understanding of complex chemistry concepts. To ideally offer an online learning environment that is accessible by all students to the greatest extent possible, this study employed the principles of the Universal Design for Learning (UDL) framework to analyse the design of online instructional resources for topics in first-year chemistry courses. Through application of UDL principles, students were provided with multiple means of representation of concepts, options for action and expression, and various avenues for engagement within the learning management system (LMS). This paper describes how the UDL framework was used to evaluate three separate independent Cases of tertiary first-year chemistry courses, including one university in the Philippines and two universities in Australia. Evaluation through surveys, focus groups, and in idual interviews revealed students’ perceptions of the usefulness of the UDL-based features. Students cited benefit from multiple forms of content delivery, animations, interactive simulations, and video recordings because they facilitated processing of information, provided alternative ways of presenting the information, allowed for varying methods for response, navigation, and flexibility, and allowed for self-evaluation of their progress. These results suggest that applying the principles of the UDL framework in instructional design of an online environment in first-year chemistry courses can support and further enhance students’ learning irrespective of their in idual contexts.
One-pot near-ambient temperature syntheses of aryl(difluoroenol) derivatives from trifluoroethanol
Publisher: Royal Society of Chemistry (RSC)
Date: 2011
DOI: 10.1039/C1OB06372C
Abstract: Difluoroalkenylzinc reagents prepared from 1-(2'-methoxy-ethoxymethoxy)-2,2,2-trifluoroethane and 1-(N,N-diethylcarbamoyloxy)-2,2,2-trifluoroethane at ice bath temperatures underwent Negishi coupling with a range of aryl halides in a convenient one pot procedure. While significant differences between the enol acetal and carbamate reagents were revealed, the Negishi protocol compared very favourably with alternative coupling procedures in terms of overall yields from trifluoroethanol.
Insights into a Community of Inquiry that emerged during academics’ emergency remote university teaching of chemistry in response to concern for students
Publisher: Informa UK Limited
Date: 20-04-2023
Enhancing academic performance and student success through learning analytics-based personalised feedback emails in first-year chemistry
Publisher: Royal Society of Chemistry (RSC)
Date: 2023
DOI: 10.1039/D3RP00032J
Abstract: Recent developments in digital technologies, including learning analytics are changing educational practices due to the wealth of information available and its utility to inform academic interventions for students. This study investigates the impact of personalised feedback emails on students’ academic performance and student success in large first-year undergraduate chemistry courses. Learning analytics was used to inform and generate feedback emails to students at various timepoints during the semester. The feedback emails to students included an evaluation of their current performance, and advice of support systems and resources to support their learning. We analysed the marks of 6334 students at three timepoints during the semester in addition to their final course grade, and compared academic performance across three years of course offerings (2019–2021). We compared students that did not receive feedback (2019 control groups, n = 2391) with students that did receive feedback (2020–2021 experimental groups, n = 3943). Our findings suggest that students receiving personalised emails during the semester were more likely to pass their first-year chemistry course. Furthermore, our data showed that sending personalised feedback emails fostered higher student success among a greater number of students within the cohort, as well as students' appraisal of the personalised feedback.
Executing and rationalizing the synthesis of a difluorinated analogue of a ring-expanded calystegine B 2
Publisher: American Chemical Society (ACS)
Date: 30-12-2012
DOI: 10.1021/JO2022845
Abstract: A difluorinated analogue of a ring-expanded calystegine B(2) and some N-protected species were prepared via microwave-mediated transannular ring-opening of an epoxyketone. The diastereofacial selectivity of the epoxidation reaction, which delivers the key intermediate, and the regioselectivity of the transannular reactions were analyzed by density functional theory (DFT) methods. The epoxidation stereoselectivity arises from simple steric control, whereas the ring-closure reactions are subject to thermodynamic control.
Iron(II)-Catalyzed Activation of Si–N and Si–O Bonds Using Hydroboranes
Publisher: American Chemical Society (ACS)
Date: 04-10-2023
The COVID Cohort: Student Transition to University in the Face of a Global Pandemic
Publisher: American Chemical Society (ACS)
Date: 14-08-2020
Iron(II) catalyzed reductive radical cyclization reactions of bromoacetals in the presence of NaBH4: optimization studies and mechanistic insights
Publisher: Elsevier BV
Date: 12-2016
N,S-Dimethyldithiocarbamyl oxalates as precursors for determining kinetic parameters for oxyacyl radicals
Publisher: Royal Society of Chemistry (RSC)
Date: 2014
DOI: 10.1039/C4CC06132B
Abstract: N , S -Dimethyldithiocarbamyl oxalates are novel, readily prepared precursors to oxyacyl radicals that are more suitable for kinetic studies than existing precursors.
Use of Monosaccharides in Metal-Catalyzed Coupling Reactions
Publisher: American Chemical Society (ACS)
Date: 07-10-2016
Organometallic catalysis for applications in radical chemistry and asymmetric synthesis
Publisher: Walter de Gruyter GmbH
Date: 04-03-2014
Abstract: Two organometallic catalysis studies are presented. The first one deals with the development of a new catalytic agent based on the mixture of a hydride and an iron salt to trigger efficient radical cyclization processes. In a second line of research, we have shown that the use of chiral anions can outperform chiral ligands in a carbocyclization reaction and a [2 + 2 + 2] cycloaddition.
First determination of the rate constant for ring-closure of an azahexenoyl radical: 6-aza-7-ethyl-5-hexenoyl
Publisher: Royal Society of Chemistry (RSC)
Date: 2010
DOI: 10.1039/C0CC01262A
Abstract: Competitive kinetic experiments utilising free radical carbonylation chemistry provide a first estimate for the rate constant for 6-endo cyclization of the 6-aza-7-ethyl-5-hexenoyl radical of (4.8 +/- 2.4) x 10(6) s(-1) at 90 degrees C in benzene, in good agreement with ONIOM-G3(MP2)-CC+COSMO-RS calculations (6.8 x 10(6) s(-1)).
Intramolecular homolytic substitution of sulfinates and sulfinamides - A computational study
Publisher: Royal Society of Chemistry (RSC)
Date: 2011
DOI: 10.1039/C1OB05043E
Abstract: Ab initio and density functional theory (DFT) calculations predict that intramolecular homolytic substitution by alkyl radicals at the sulfur atom in sulfinates proceeds through a smooth transition state in which the attacking and leaving radicals adopt a near collinear arrangement. When forming a five-membered ring and the leaving radical is methyl, G3(MP2)-RAD//ROBHandHLYP/6-311++G(d,p) calculations predict that this reaction proceeds with an activation energy (ΔE(1)(‡)) of 43.2 kJ mol(-1). ROBHandHLYP/6-311++G(d,p) calculations suggest that the formation of five-membered rings through intramolecular homolytic substitution by aryl radicals at the sulfur atom in sulfinates and sulfinamides, with expulsion of phenyl radicals, proceeds with the involvement of hypervalent intermediates. These intermediates further dissociate to the observed products, with overall energy barriers of 45-68 kJ mol(-1), depending on the system of interest. In each case, homolytic addition to the phenyl group competes with substitution, with calculated barriers of 51-78 kJ mol(-1). This computational study complements and provides insight into previous experimental observations.
Rhodium(i)-catalysed cycloisomerisation/6π electrocyclisation of 5-(ethynylamino)pent-2-yn-1-yl esters to 2,3-dihydrobenzo[f]indoles
Publisher: Royal Society of Chemistry (RSC)
Date: 2022
DOI: 10.1039/D2NJ01992B
Abstract: A rare instance in rhodium catalysis of an in situ formed rhodacycle that undergoes a formal 1,8-acyloxy migration-initiated reductive elimination.
Intramolecular homolytic substitution in selenoxides and selenones
Publisher: Elsevier BV
Date: 12-2016
Multi-component orbital interactions during oxyacyl radical addition reactions involving imines and electron-rich olefins
Publisher: Royal Society of Chemistry (RSC)
Date: 2007
DOI: 10.1039/B714324A
Abstract: Ab initio and DFT calculations reveal that oxyacyl radicals add to imines and electron-rich olefins through simultaneous SOMO-pi*, SOMO-pi and pi*-HOMO interactions between the radical and the radicalophile. At the BHandHLYP/aug-cc-pVDZ level, energy barriers of 20.3 and 22.0 kJ mol(-1) are calculated for the attack of methoxycarbonyl radical at the carbon and nitrogen ends of methanimine, respectively. In comparison, barriers of 22.0 and 8.6 kJ mol(-1) are calculated at BHandHLYP/aug-cc-pVDZ for reaction of methoxycarbonyl radical at the 1- and 2-positions in aminoethylene, respectively. Natural bond orbital (NBO) analysis at the BHandHLYP/6-311G** level of theory reveals that SOMO-pi*, SOMO-pi and pi*-LP interactions are worth 111, 394 and 55 kJ mol(-1) respectively in the transition state (8) for reaction of oxyacyl radical at the nitrogen end of methanimine similar interactions are observed for the chemistry involving aminoethylene. These multi-component interactions are responsible for the unusual motion vectors associated with the transition states involved in these reactions.
Chiral Gold Complex Catalyzed Cycloisomerization/Regio- and Enantioselective Nitroso-Diels–Alder Reaction of 1,6-Diyne Esters with Nitrosobenzenes
Publisher: American Chemical Society (ACS)
Date: 03-06-2022
An ab initio and DFT study of radical addition reactions of imidoyl and thioyl radicals to methanimine
Publisher: Royal Society of Chemistry (RSC)
Date: 2011
DOI: 10.1039/C1OB05105A
Abstract: Ab initio and DFT calculations reveal that both imidoyl and thioyl radicals add to the nitrogen end of methanimine through simultaneous SOMO-π*(imine), SOMO-π(imine), SOMO-LP(N) and π*(radical)-LP(N) interactions between the radical and the imine. At the CCSD(T)/cc-pVDZ//BHandHLYP/cc-pVTZ level of theory, barriers of 13.8 and 26.1 kJ mol(-1) are calculated for the attack of the methylimidoyl radical at the carbon- and nitrogen- end of methanimine, respectively, indicating that the imidoyl radial has a preference for addition to the nitrogen end of imine. On the other hand, barriers of 25.1 and 13.4 kJ mol(-1) are calculated at the same level of theory for the addition reaction of the methanethioyl radical at the carbon- and nitrogen- end of methanimine, respectively. Natural bond orbital (NBO) analysis at the BHandHLYP/6-311G** level of theory reveals that SOMO-π*(imine), SOMO-π(imine), SOMO-LP(N) and π*(radical)-LP(N) interactions are worth 111, 89, 115 and 17 kJ mol(-1), respectively, in the transition state (4) for the reaction of methylimidoyl radical at the nitrogen end of methanimine similar interactions are observed for the chemistry involving all the radicals studied here. These multi-component interactions are responsible for the unusual motion vectors associated with the transition states involved in these reactions.
Implementing blended first-year chemistry in a developing country using online resources
Publisher: The Online Learning Consortium
Date: 03-2022
Abstract: Decades of rapid development in information and communication technologies (ICTs) have resulted in tremendous global evolution in computer and online instruction. Many developing countries, however, are still struggling to successfully integrate ICTs in their teaching and learning practices, subsequently leading to slower rates of adapting digital learning pedagogies. To understand how blended instruction might operate in higher education in a developing country, this study explored students’ perspectives on the implementation of blended learning in a first-year chemistry program delivered in the Philippines. Through the resource-based learning framework, multiple types of online learning resources were employed for blended delivery of topics on periodic trends, chemical bonding, Lewis structures, molecular shape and polarity through the learning management system, Moodle. To understand the students’ experiences, a mixed methods approach was employed through a survey, focus groups, and learning analytics. Despite the scarcity of technological resources (such as access to a reliable internet connection) 57.5% of 447 student respondents favoured blended learning because of the flexibility, wider access to different types of interactive learning resources, variety of learning activities, and perceived increase in learning productivity. While the majority of respondents (75.7%) had ICT skills sufficient for education, much fewer had access to computers (19.7%). 40.0% of students self-reported that they preferred a traditional mode of instruction primarily due to the perceived difficulty of chemistry as subject matter and the students’ perceived need for a physically-present teacher to explain concepts face-to-face and to respond to questions that would arise anytime during the learning period.
Synthesis, structural and DFT analysis of a binuclear nickel(II) complex with the 1,4-bis[2-[2-(diphenylphosphino)benzylidene]]phthalazinylhydrazone ligand
Publisher: Springer Science and Business Media LLC
Date: 27-05-2019
Iron and cobalt catalysis: new perspectives in synthetic radical chemistry
Publisher: Royal Society of Chemistry (RSC)
Date: 2020
DOI: 10.1039/D0CS00969E
Abstract: Iron and cobalt complexes are at the origin of high valuable synthetic pathways involving radical intemediates.
Homolytic Substitution Chemistry: From James Franz to Antihypertensives
Publisher: Wiley
Date: 03-07-2012
Intramolecular homolytic substitution of seleninates - A computational study
Publisher: Elsevier BV
Date: 2012
Elucidating Dramatic Ligand Effects on SET Processes: Iron Hydride versus Iron Borohydride Catalyzed Reductive Radical Cyclization of Unsaturated Organic Halides
Publisher: American Chemical Society (ACS)
Date: 27-09-2017
Minisci‐Type Alkylation of N‐Heteroarenes by N‐(Acyloxy)phthalimide Esters Mediated by a Hantzsch Ester And Blue LED Light
Publisher: Wiley
Date: 05-01-2022
Abstract: A synthetic method that enables the Hantzsch ester‐mediated Minisci‐type C2‐alkylation of quinolines, isoquinolines and pyridines by N ‐(acyloxy)phthalimide esters (NHPI) under blue LED (light emitting diode) light (456 nm) is described. Achieved under mild reaction conditions at room temperature, the metal‐free synthetic protocol was shown to be applicable to primary, secondary and tertiary NHPIs to give the alkylated N ‐heterocyclic products in yields of 21–99%. On introducing a chiral phosphoric acid, an asymmetric version of the reaction was also realised and provided product enantiomeric excess (ee) values of 53–99%. The reaction mechanism was delineated to involve excitation of an electron‐donor acceptor (EDA) complex, formed from weak electrostatic interactions between the Hantzsch ester and NHPI, which generates the posited radical species of the redox active ester that undergoes addition to the N ‐heterocycle. magnified image
The transition to first year chemistry: student, secondary and tertiary educator's perceptions of student preparedness
Publisher: Royal Society of Chemistry (RSC)
Date: 2021
DOI: 10.1039/D1RP00068C
Abstract: Student preparedness is an essential component of transition to university influenced by a broad suite of attributes including academic aptitude, prior knowledge, self-efficacy, self-confidence and a complex assortment of study and life skills. In the case of chemistry education, students' self-perceptions of preparedness are intrinsically linked to prior learning of both theory and hands on laboratory experiences, and interwoven with intricacies such as science identity, gender, and secondary school background. Accordingly, this study sought to establish a deeper understanding of learners' and educators' perceptions of student preparedness upon commencing tertiary studies in chemistry. The research used a mixed methods approach including questionnaires, focus groups, and interviews to capture the breadth and depth of these perceptions. 924 students from the first year chemistry cohort completed either one or two surveys designed to capture their prospective and retrospective self-perceptions of how well prepared they were for the course. Nine of these students also participated in focus groups. Secondary educator's views were captured via a qualitative online survey to conveniently enable a broad cohort to be s led, while tertiary educators from the institution where this study was conducted were interviewed in person. Key findings from students include: a strong correlation between self-perception of preparedness and academic performance, those with negative perceptions of preparedness are genuinely an at-risk category, an overall positive shift for perceptions of preparedness for students as they get to the end of the semester (which is more pronounced for students who attended private secondary schools), and a significant disparity between genders at the start of the semester that was no longer present by the end. Additional key findings include the disparity between secondary and tertiary educator's perspectives of how well prepared students are for the transition to tertiary level chemistry studies. While the former have a favourable view, the latter consider many students to be quite poorly prepared, with each cohort ultimately focusing on different attributes. We suggest the implications for these findings include the importance of emphasising expectations of students as they commence their courses, and that work still needs to be done to align the perspectives of educators at all levels when it comes to preparing and supporting students as they transition to higher education.
Organocatalytic α‐Aminoalkylation of Azomethine Imines by α‐Silylamines under Blue LED Light
Publisher: Wiley
Date: 10-07-2023
Abstract: A synthetic method to prepare 1,2‐diamines efficiently that relies on the 4CzPN‐catalysed α ‐aminoalkylation of azomethine imines by secondary and tertiary α ‐silylamines under blue light emitting diode (LED) light (456 nm) is described. Achieved under metal‐ and additive‐free reaction conditions at room temperature, the synthetic protocol was shown to afford product yields up to 99% and applicable to the late‐stage functionalisation of three drug molecules and the gramme‐scale preparation of one ex le.
Organocatalytic alkylation and photoorganocatalyst-free acylation of azomethine imines by Hantzsch esters under blue LED light
Publisher: Royal Society of Chemistry (RSC)
Date: 2023
DOI: 10.1039/D3NJ03780K
Multiorbital interactions during acyl radical addition reactions involving imines and electron-rich olefins
Publisher: American Chemical Society (ACS)
Date: 19-12-2008
DOI: 10.1021/JO701825Y
Abstract: Ab initio and DFT calculations reveal that acyl radicals add to imines and electron-rich olefins through simultaneous SOMO --> pi*, pi --> SOMO, and HOMO --> pi*C=O interactions between the radical and the radicalophile. At the CCSD(T)/aug-cc-pVDZ//QCISD/cc-pVDZ level, energy barriers of 15.6 and 17.9 kJ mol(-1) are calculated for the attack of the acetyl radical at the carbon and nitrogen ends of methanimine, respectively. These barriers are 17.1 and 20.4 kJ mol(-1) at BHandHLYP/cc-pVDZ. In comparison, barriers of 34.0 and 23.4 kJ mol(-1) are calculated at BHandHLYP/cc-pVDZ for reaction of the acetyl radical at the 1- and 2-positions in aminoethylene, repectively. Natural bond orbital (NBO) analysis at the BHandHLYP/6-311G** level of theory reveals that SOMO --> pi*imine, pi imine--> SOMO, and LPN --> pi*C=O interactions are worth 90, 278, and 138 kJ mol-1, respectively, in the transition state (2) for reaction of acetyl radical at the nitrogen end of methanimine similar interactions are observed for the chemistry involving aminoethylene. These multiorbital interactions are responsible for the unusual motion vectors associated with the transition states involved in these reactions. NBO analyses for the remaining systems in this study support the hypothesis that the acetyl radical is ambiphilic in nature.
Related Organisations
Related Funding Activities
Discovery Projects - Grant ID: DP220102622
Start Date: 03-2023
End Date: 08-2026
Amount: $430,000.00
Funder: Australian Research Council
View Funded Activity