21st Annual Student Research Conference
Computational Exploration of the Reactivity of Phosphonothiolates with Grignard Reagetns
Emily C. Hopson
Dr. Eric V. Patterson, Faculty Mentor
The chemical warfare agent VX [O-ethyl S-(2-diisopropylamino)ethyl methylphosphonothiolate] is a potent neurotoxin, which leads to death by asphyxiation. Chemical detoxification of VX requires cleavage of the P-S bond, which can be affected by nucleophilic attack. However, no two nucleophiles show the same chemistry. For example, hydroxide leads to a majority of P-S cleavage, but also gives toxic P-O cleavage products while hydroperoxide gives exclusive P-S cleavage. Conversely, Grignard reagents are believed to lead to primarily P-O cleavage. Previous computational studies on a VX simulant, O,S-dimethyl methylphosphonothiolate, have been used to rationalize the difference in reactivity between hydroxide and hydroperoxide. We now report an exploration of the reaction of the same VX simulant with methyl Grignard.
Keywords: VX, computational, chemistry, neurotoxin, mechanism, reaction, phosphonothiolate, detoxification
Topic(s):Chemistry
Presentation Type: Oral Paper
Session: 3-1
Location: VH 1320
Time: 8:15