Journal article

NMR Chemical Shift and Methylation of 4-Nitroimidazole: Experiment and Theory

Frederick Backler, Marc Antoine Sani, Frances Separovic, Vladislav Vasilyev, Feng Wang

Australian Journal of Chemistry | CSIRO Publishing | Published : 2020


Nitroimidazoles and derivatives are a class of active pharmaceutical ingredients (APIs) first introduced sixty years ago. As anti-infection agents, the structure–activity relationships of nitroimidazole compounds have been particularly difficult to study due to their low reduction potentials and unique electronic structures. In this study, we combine dynamic nuclear polarization (DNP)-enhanced solid-state (100 K), solid-state (298 K), and 1H-13C heteronuclear single quantum coherence (HSQC) solution-state NMR techniques (303 K) with density functional theory (DFT) to study the 1H, 13C, and 15N chemical shifts of 4-nitroimidazole (4-NI) and 1-methyl-4-nitroimidazole (CH3-4NI). The 4-NI chemic..

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Awarded by Australian Research Council

Funding Acknowledgements

FB acknowledges the Research Training Program Scholarships (RTPS) from the Australian Government and thanks Dr Subhojyoti Chatterjee and Dr Shawkat Islam for technical assistance. Swinburne University supercomputing (OzSTAR) and National Computational Infrastructure (NCI), supported by the Australian Government, are acknowledged for computing facilities. FS and MAS acknowledge the Australian Research Council for LIEF grant LE160100120 providing funding of DNP-NMR at the Bio21 Institute NMR facility. FW thanks University of Melbourne for hosting of sabbatical visit. The authors thank Professor Jonathan White, University of Melbourne, for gift of the CH<INF>3</INF>-4NI sample. Finally, they thank Professor Robert Metzger (SDSU) for useful discussion regarding NMR calculations.