Oxime functionality in surfactant self-assembly: An overview on combating toxicity of organophosphates

Singh, Namrata; Karpichev, Yevgen; Tiwari, Amit K.; Kuča, Kamil; Ghosh, Kallol K.

doi:10.1016/j.molliq.2015.04.010

Cited by 37 publications

(15 citation statements)

References 158 publications

(103 reference statements)

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“…[11] Thecapacity of oximes andt heir anions to form metal coordinationc omplexesc an be used in multiple-analyte and/or electrochemical systemsf or the detection of metal ions or other organic species. This property,w hich has attractedc onsiderable attention towards oximes in the detoxification of organophosphorus compounds, levels off as the acidity of the parent oxime decreases.…”

Section: Electrochemical Properties Acidityand Oàhbond Dissociationmentioning

confidence: 99%

“…This property,w hich has attractedc onsiderable attention towards oximes in the detoxification of organophosphorus compounds, levels off as the acidity of the parent oxime decreases. [11] Thecapacity of oximes andt heir anions to form metal coordinationc omplexesc an be used in multiple-analyte and/or electrochemical systemsf or the detection of metal ions or other organic species. [41] The redox properties and acidity of oximes are important properties for assessing their potential for these applications.…”

Section: Electrochemical Properties Acidityand Oàhbond Dissociationmentioning

confidence: 99%

“…Oximate ions are of interestf or the decontamination of toxic metal ions [10] and organophosphorus compounds. [11] Oximesa re known to exist in two configurations, with the residue of highest priority either E or Z with respect to the oxime OH group. The photoinduced switch of the E/Z configurationi ni mines, oximes and hydrazones has been extensively investigated in the field of light-driven molecular machines (see Ref.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

2‐(Hydroxyimino)aldehydes: Photo‐ and Physicochemical Properties of a Versatile Functional Group for Monomer Design

Gentili

Nardi

Antignano

et al. 2018

Chemistry A European J

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In the context of our research on stimuli-responsive polymers bearing the 2-(hydroxyimino)aldehyde (HIA) group, we have explored the photochemical behavior and physicochemical properties of a number of HIAs. Interpretation of the experimental data is supported by quantum mechanical calculations. HIAs are expected to undergo photoisomerization, chelate metal ions, yield hydrogen-bonded dimers or oligomers, exhibit relatively low pK s, and form >C=NO radicals through OH hydrogen abstraction or oxidation of the oximate ion. Besides the well-established E/Z oxime photoisomerism, we observed a Norrish-Yang cyclization resulting in cyclobutanol oximes, to our knowledge not previously described in the literature. The acidity, bond dissociation enthalpies, and electrochemical properties of the HIAs are compared with literature data of simple oximes. The results are discussed in relation to the many potential applications for HIAs, with emphasis on the synthesis of novel HIA-containing responsive polymers.

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Section: Electrochemical Properties Acidityand Oàhbond Dissociationmentioning

confidence: 99%

Section: Electrochemical Properties Acidityand Oàhbond Dissociationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

2‐(Hydroxyimino)aldehydes: Photo‐ and Physicochemical Properties of a Versatile Functional Group for Monomer Design

Gentili

Nardi

Antignano

et al. 2018

Chemistry A European J

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“…In 1930, toxic and insecticidal properties of these compounds were reported [4]. Since then, there has been growing interest in the study of this class of compounds due to their possible application as agrochemicals and chemical weapons [5,6]. e high toxicity of the OP compounds is associated with high affinity for the acetylcholinesterase enzyme [7,8].…”

Section: Introductionmentioning

confidence: 99%

Detection of Chemical Weapon Agents Using Spectroscopic Probes: A Computational Study

Braga

Silva

Mancini

et al. 2020

Journal of Chemistry

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Organophosphorus compounds are organic compounds widely employed in agriculture as well as in chemical weapons. The use in agriculture is due to their insecticidal properties. However, in chemical warfare, the use of organophosphorus is associated with acetylcholinesterase inhibition, which promotes the cholinergic syndromes. In this line, the fast detection of this class of compound is crucial for the determination of environmental exposure. This improved detection will naturally allow for more prompt courses of treatment depending on the contaminant findings. In this perspective, the dipyrrinone oxime (1) was employed for the detection of organophosphorus compounds that are employed as nerve agents, such as cyclosarin, sarin, soman, diethyl chlorophosphate, diisopropylfluorophosphate, 2-(dimethylamino)ethyl N,N-dimethylphosphoramidofluoridate, O-ethyl-S-[2-(diethylamino)ethyl]methylphosphonothioate, O-ethyl-S-[2(diisopropylamino)ethyl] methylphosphonothioate, and O,O-diethyl-S-[2-(diethylamino)ethyl] phosphorothioate, through fluorescent emission. The thermodynamics and kinetic parameters as well as spectroscopic properties of the complexes formed for 1 and all organophosphorus compounds previously cited were investigated by means of theoretical calculations. From our findings, only the diethyl chlorophosphate, 2-(dimethylamino)ethyl N,N-dimethylphosphoramidofluoridate, and O,O-diethyl-S-[2-(diethylamino)ethyl] phosphorothioate emitted fluorescence in the hexane, toluene, chloroform, dichloromethane, methanol, acetonitrile, water, and dimethyl sulfoxide solvents. The study of the absorption wavelength with the most polar solvent showed higher values compared to apolar solvents. In the same solvent, for instance, soman in hexane showed the lowest absorption wavelength value, 324.5 nm, and DCP the highest value, 330.8 nm. This behavior was observed in other tested solvents. The thermodynamic parameters indicate negative Gibbs free energy (ΔG) values for the O-ethyl-S-[2(diisopropylamino)ethyl] methylphosphonothioate with 1 reaction. On the other hand, the sarin and cyclosarin revealed the lowest Gibbs free energy (ΔG‡) values, being kinetically favorable and presenting more reactivity.

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“…[33,34] Actual research directions in this area are improvement in the efficacy of catalytic systems and the use of environmentally friendly processes. The latter can be achieved by using green solvents, [35,36] biodegradable surfactants, [37] αnucleophilic systems [38] and lowering surfactant concentration. It can be achieved by using dimeric (gemini) or polymeric surfactants that have much lower critical micelle concentration (CMC) and higher binding constants than monomeric surfactants.…”

Section: Introductionmentioning

confidence: 99%

Self‐Assembled Quaternary Ammonium‐Containing Comb‐Like Polyelectrolytes for the Hydrolysis of Organophosphorous Esters: Effect of Head Groups and Counter‐Ions

et al. 2020

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The aim of this work was to increase the efficiency of catalytic systems for the hydrolytic cleavage of 4‐nitrophenyl esters of phosphonic acids. Quaternary ammonium‐containing comb‐like polyelectrolytes («polymerized micelles») with ester cleavable fragments and a low aggregation threshold were used as catalysts. The synthesis of poly(11‐acryloyloxyundecylammonium) surfactants with different counterions (Br−, NO3−, CH3C6H4SO3−) and head groups was realized by micellar free‐radical polymerization. Molecular weight, critical association concentration, particle sizes and solubilization properties toward Orange OT were determined. Self‐assemblies organized by poly(11‐acryloyloxyundecyltrimethyl ammonium) bromide successfully catalyze the hydrolysis of 4‐nitrophenyl butylchloromethylphosphonate up to two orders of magnitude compared to aqueous alkaline hydrolysis. The development of these catalysts is promising for industrial applications and organophosphorus compound detoxification.

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Oxime functionality in surfactant self-assembly: An overview on combating toxicity of organophosphates

Cited by 37 publications

References 158 publications

2‐(Hydroxyimino)aldehydes: Photo‐ and Physicochemical Properties of a Versatile Functional Group for Monomer Design

2‐(Hydroxyimino)aldehydes: Photo‐ and Physicochemical Properties of a Versatile Functional Group for Monomer Design

Detection of Chemical Weapon Agents Using Spectroscopic Probes: A Computational Study

Self‐Assembled Quaternary Ammonium‐Containing Comb‐Like Polyelectrolytes for the Hydrolysis of Organophosphorous Esters: Effect of Head Groups and Counter‐Ions

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