Recent Advances on the Decomposition of Neurotoxic Phosphorous Triesters

Wanderlind, Eduardo H.; Medeiros, Michelle; Souza, Bruno S.; Fiedler, Haidi D.; Nome, Faruk

doi:10.5935/1984-6835.20140040

Cited by 2 publications

(1 citation statement)

References 21 publications

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“…This path should be the least favorable one with imidazole (no reports to date) 19,21 and occurs predominantly with alpha-nucleophiles. 25 In order to infer how the reactions occur, a thorough kinetic study was carried out as well as it was followed by 1 H and 31 P NMR, to confirm possible intermediates and products.…”

Section: Resultsmentioning

confidence: 99%

Are Imidazoles Versatile or Promiscuous in Reactions With Organophosphates? Insights From the Case of Parathion

Silva

Orth

2019

J. Braz. Chem. Soc.

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Is the broad mechanistic versatility of imidazole towards organophosphates (OPs), that has inspired many catalysts and sensors, beneficial? Herein, a thorough analysis is given seeking to unravel this puzzle. For OPs from the P=O family, imidazole attacks the phosphorus atom exclusively (N-phosphorylates). With the P=S family which are less reactive, an unusual N-alkylation predominates. Surprisingly, imidazole reacts with methyl parathion exclusively at the aliphatic carbon, whilst for the ethylated analogue parathion, imidazole reacts by two pathways: at both the phosphorus and aliphatic carbon, with predominance for the latter. The preference for the electrophilic center can be modulated by the pH. Overall, a mechanistic structure-related trend is observed: imidazole tends to prefer other electrophilic centers than the phosphorus for less reactive OPs. Moreover, this gives important insights concerning the challenging chemistry of imidazole alkylation and the outcomes for monitoring systems that depend on the detection of degradation products. Finally, a thorough comparison with the literature is presented seeking to understand how imidazole reacts towards various OPs. We suggest that the promiscuity of imidazole boosts up its versatility.

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Section: Resultsmentioning

confidence: 99%