Ranking Oxidant Sensitiveness: A Guide for Synthetic Utility

Madeleine A. Dallaston; Christian J. Bettencourt; Dr. 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

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

Research output: Contribution to journal › Article › peer-review

19 Citations (Scopus)

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).

Original language	English
Pages (from-to)	9614-9618
Number of pages	5
Journal	Chemistry - A European Journal
Volume	25
Issue number	41
DOIs	https://doi.org/10.1002/chem.201902036
Publication status	Published - 22 Jul 2019

Keywords

differential scanning calorimetry
electrostatic discharge experiments
impact sensitiveness
oxidant

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title = "Ranking Oxidant Sensitiveness: A Guide for Synthetic Utility",

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",

author = "Dallaston, \{Madeleine A.\} and Bettencourt, \{Christian J.\} and Chow, \{Dr. Sharon\} and Joshua Gebhardt and Jordan Spangler and Johnston, \{Martin R.\} and Craig Wall and Brusnahan, \{Jason S.\} and Williams, \{Craig M.\}",

year = "2019",

month = jul,

day = "22",

doi = "10.1002/chem.201902036",

language = "English",

volume = "25",

pages = "9614--9618",

journal = "Chemistry - A European Journal",

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TY - JOUR

T1 - Ranking Oxidant Sensitiveness

T2 - A Guide for Synthetic Utility

AU - Dallaston, Madeleine A.

AU - Bettencourt, Christian J.

AU - Chow, Dr. Sharon

AU - Gebhardt, Joshua

AU - Spangler, Jordan

AU - Johnston, Martin R.

AU - Wall, Craig

AU - Brusnahan, Jason S.

AU - Williams, Craig M.

PY - 2019/7/22

Y1 - 2019/7/22

N2 - 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).

AB - 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).

KW - differential scanning calorimetry

KW - electrostatic discharge experiments

KW - impact sensitiveness

KW - oxidant

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DO - 10.1002/chem.201902036

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SN - 0947-6539

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SP - 9614

EP - 9618

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 41

ER -

Ranking Oxidant Sensitiveness: A Guide for Synthetic Utility

Abstract

Keywords

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Corrigendum: Ranking Oxidant Sensitiveness: A Guide for Synthetic Utility (Chemistry – A European Journal, (2019), 25, 10.1002/chem.201902036)

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