Reactions of Chemical Warfare Agents With DS2: Product Identification by NMR. 2.2-Chloroethyl Sulfides

摘要

C NMR spectroscopy was used to monitor the reactions of HD and 2-chloroethylmethyl sulfide (CEMS) with DS2. The 2-chloroethyl sulfides were found to rapidly dehydrohalogenate in DS2, forming their corresponding vinyl elimination products. The presence of water had an adverse effect on the solubility of the 2-chloroethyl sulfide: in DS2, and variations in the reaction profile as a function of added water showed that the decreased reactivity of the DS2/H2O solutions results from a change in reaction mechanism. As the amount of H2O increases, the reaction mechanism changes from a rapid elimination to a much slower nucleophilic SN1 process. The major products from the SN1 reaction result from substitution of the chloride in the 2-chloroethyl sulfides by the diethylenetriamine (DETA) in the DS2.... CEMS, Decontamination, Elimination, HD, Nucleophilic substitution, NMR, DS2.