β,β'-DICHLORO-DIETHYL ETHER. THE OXYGEN ANALOG OF MUSTARD GAS.<sup>1</sup>

Kamm, Oliver; Waldo, John H.

doi:10.1021/ja01443a013

Cited by 18 publications

(6 citation statements)

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“…SM is quite reactive as compared to other alkylating agents such as oxygen mustard, benzyl bromide, and ethyl iodide. This is attributed to the fact that sulfur atom in SM undergoes neighboring group participation forming electrophilic three-membered episulfonium ion (Scheme ) thus making mustard gas extremely reactive for nucleophilic attack over these analytes including oxygen mustard . Given sensing conditions, i.e., 60 °C for 1 min is not sufficient for 1 to react with these less reactive anlaytes.…”

Section: Resultsmentioning

confidence: 99%

“…This is attributed to the fact that sulfur atom in SM undergoes neighboring group participation forming electrophilic three-membered episulfonium ion (Scheme 1) thus making mustard gas extremely reactive for nucleophilic attack over these analytes including oxygen mustard. 23 Given sensing conditions, i.e., 60 °C for 1 min is not sufficient for 1 to react with these less reactive anlaytes. Although, performing the reaction under harsh conditions such as high temperature (80 °C) and prolong reaction time (16 h) may also lead to product formation, 20 which is not the desired situation in our case.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Chemodosimeter for Selective and Sensitive Chromogenic and Fluorogenic Detection of Mustard Gas for Real Time Analysis

et al. 2018

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Since the first use of chemical warfare agents (CWA) (1915) to the recent attacks in Syria (2017) on mankind, there have been many incidents where CWA have claimed thousands of lives and left many more contaminated. In order to provide the appropriate and immediate medical counter measure to the victims, the exact classification of these chemical agents within few minutes on the field itself using a rapid and simple detection technique is extremely important to save the lives of the effected people. This has motivated all of us to explore the novel strategies/detection systems that can be field deployable with better selectivity and greater sensitivity. In view of this, we present a novel chemosensor, 3,6-bis(dimethylamino)-9(10H)-acridine thione (1), that can detect mustard gas and its simulant by both chromogenic and fluorogenic methods. For the first time, a single probe was able to demonstrate the detection with unprecedented selectivity over most probable interferences (nerve agents and alkylating agents) including solvents, acids, and bases which are routinely present in the environment. The desired level of sensitivity by naked eyes (0.04 mg/mL), UV spectroscopy (0.02 mg/mL), and fluorescence spectroscopy (0.005 mg/mL) makes this method truly field deployable. For the spot detection on the affected areas, a handy and potable chemosensor kit was also fabricated. This paper provides a simple, highly specific, and easy to use method in "actual sense" that not only detects the agents in the solution phase but also in the contaminated samples.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Chemodosimeter for Selective and Sensitive Chromogenic and Fluorogenic Detection of Mustard Gas for Real Time Analysis

et al. 2018

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“…75 Reactions between aromatic primary amines and BCEE produce 4-aryl substituted morpholines (Fig. 10, f ), 5,[75][76][77][78][79] while reaction with ammonia results in multiple products. 80,81 Reactivity of surrogate mustards in CDCl 3…”

Section: Reactivity Of Oxygen Mustardsmentioning

confidence: 99%

“…Mustard gas, β,β′-dichloroethyl sulfide or bis(β-chloroethyl) sulfide (HD), is a vesicant or blistering agent noted for its use in chemical warfare. [1][2][3][4] Its simple oxygen and nitrogen analogs, in which the central sulfur atom has been replaced by oxygen and nitrogen, respectively, are known as the oxygen mustard, bis-(β-chloroethyl) ether (BCEE), 5 and the nitrogen mustards, 2,2′dichlorodiethylamines (e.g., HN1, HN2, HN3) (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Sulfur, oxygen, and nitrogen mustards: stability and reactivity

et al. 2012

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Mustard gas, bis(β-chloroethyl) sulfide (HD), is highly toxic and harmful to humans and the environment. It comprises one class of chemical warfare agents (CWAs) that was used in both World Wars I and II. The three basic analogues or surrogates are: the monochloro derivative, known as the half mustard, 2-chloroethyl ethyl sulfide (CEES); an oxygen analogue, bis(β-chloroethyl) ether (BCEE); and several nitrogen analogues based on the 2,2'-dichlorodiethylamine framework (e.g., HN1, HN2, and HN3). The origin of their toxicity is considered to be from the formation of three-membered heterocyclic ions, a reaction that is especially accelerated in aqueous solution. The reaction of these cyclic ion intermediates with a number of important biological species such as DNA, RNA and proteins causes cell toxicity and is responsible for the deleterious effects of the mustards. While a number of studies have been performed over the last century to determine the chemistry of these compounds, early studies suffered from a lack of more sophisticated NMR and X-ray techniques. It is now well-established that the sulfur and nitrogen mustards are highly reactive in water, while the oxygen analog is much more stable. In this study, we review and summarize results from previous studies, and add results of our own studies of the reactivity of these mustards toward various nonaqueous solvents and nucleophiles. In this manner a more comprehensive evaluation of the stability and reactivity of these related mustard compounds is achieved.

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“…1), are also highly toxic and harmful to humans and the environment. Oxygen analogs, in which the central sulfur or nitrogen atom has been replaced by oxygen is known as oxygen mustard, bis-(2-chloroethyl) ether [9].…”

Section: Introductionmentioning

confidence: 99%

Mustard carbonate analogues

Aricò

Tundo

2015

Pure and Applied Chemistry

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Sulfur and nitrogen (half-)mustard carbonate analogues are a new class of compounds, easily synthesized\ud by methoxycarbonylation reaction of the parent alcohols with dialkyl carbonates. In this work, their\ud reactivity as novel, green electrophiles is reported. Reactions have been conducted in autoclave conditions\ud at high temperature (180 °C), under pressure and in absence of any base, as well as, in neat at atmospheric\ud pressure, lower temperature (150 °C) and in the presence of a catalytic amount of a base. Several nucleophiles\ud have been investigated resulting, in some cases, in unexpected compounds, i.e., six-membered heterocycle\ud piperidine. Reaction mechanism and kinetics have been studied confirming that these compounds retain the\ud anchimeric effect of their mustard gas analogues, without being toxic. Noteworthy, a symmetrical nitrogen\ud mustard carbonate has also been employed as reagent in the preparation of a new family of macrocycles i.e.,\ud azacrowns, before not easily accessible

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β,β'-DICHLORO-DIETHYL ETHER. THE OXYGEN ANALOG OF MUSTARD GAS.¹

Cited by 18 publications

References 0 publications

Chemodosimeter for Selective and Sensitive Chromogenic and Fluorogenic Detection of Mustard Gas for Real Time Analysis

Chemodosimeter for Selective and Sensitive Chromogenic and Fluorogenic Detection of Mustard Gas for Real Time Analysis

Sulfur, oxygen, and nitrogen mustards: stability and reactivity

Mustard carbonate analogues

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β,β'-DICHLORO-DIETHYL ETHER. THE OXYGEN ANALOG OF MUSTARD GAS.1

Cited by 18 publications

References 0 publications

Chemodosimeter for Selective and Sensitive Chromogenic and Fluorogenic Detection of Mustard Gas for Real Time Analysis

Chemodosimeter for Selective and Sensitive Chromogenic and Fluorogenic Detection of Mustard Gas for Real Time Analysis

Sulfur, oxygen, and nitrogen mustards: stability and reactivity

Mustard carbonate analogues

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β,β'-DICHLORO-DIETHYL ETHER. THE OXYGEN ANALOG OF MUSTARD GAS.¹