Ranking Oxidant Sensitiveness: A Guide for Synthetic Utility

Madeleine A Dallaston; Christian J Bettencourt; Sharon Chow; Joshua Gebhardt; Jordan Spangler; Martin R Johnston; Craig Wall; Jason S Brusnahan; Craig M Williams

doi:10.1002/chem.201902036

Ranking Oxidant Sensitiveness: A Guide for Synthetic Utility

Chemistry. 2019 Jul 22;25(41):9614-9618. doi: 10.1002/chem.201902036. Epub 2019 Jun 27.

Authors

Madeleine A Dallaston¹, Christian J Bettencourt¹, Sharon Chow¹, Joshua Gebhardt², Jordan Spangler², Martin R Johnston², Craig Wall³, Jason S Brusnahan³, Craig M Williams¹

Affiliations

¹ School of Chemistry and Molecular Biosciences, University of Queensland, Brisbane, 4072, Australia.
² Flinders Institute for Nanoscale Science and Technology, College of Science and Engineering, Flinders University, South Australia, 5042, Australia.
³ Defence Science and Technology Group, Edinburgh, South Australia, 5111, Australia.

PMID: 31245899
DOI: 10.1002/chem.201902036

Abstract

Common oxidants used in chemical synthesis, including newly developed perruthenates, were evaluated in the context of understanding (and better appreciating) the sensitiveness and associated potential hazards of these reagents. Analysis using sealed cell differential scanning calorimetry (scDSC) facilitated Yoshida correlations, which were compared to impact sensitiveness and electrostatic discharge experiments (ESD), that enabled sensitiveness ranking. Methyltriphenylphoshonium perruthenate (MTP3, 8), isoamyltriphenylphosphonium perruthenate (ATP3, 7) and tetraphenylphosphonium perruthenate (TP3, 9) were found to be the most sensitive followed by 2-iodoxybenzoic acid (IBX, 2) and benzoyl peroxide (BPO, 10), whereas the most benign were observed to be Oxone (12), manganese dioxide (MnO₂ , 13), and N-bromosuccinimide (NBS, 17).

Keywords: differential scanning calorimetry; electrostatic discharge experiments; impact sensitiveness; oxidant.