Comparative study of nucleophilic efficacy of pralidoxime towards phosphorus, sulfur and thiophosphorus based esters

Tiwari, Shuchi; Ghosh, Kallol K.; Marek, Jan; Kuča, Kamil

doi:10.1007/s11144-009-0072-7

Cited by 9 publications

(6 citation statements)

References 34 publications

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“…PAM and other oximes act as strong nucleophiles in deacylation and dephosphorylation of esters, and their efficiency in dephosphorylation can be enhanced by conversion into corresponding oximate anions, which in the case of PAM should be termed zwitterions (Figure 2) 16,20,21 Reactivity of the oximates can suffer a saturation effect and decay with increasing basicity in aqueous solution above a pH of 9, 20 and thus we performed the conversion of PAM to PAMNa at pH 8.6, i.e., just above the pK a value of 8.23 reported for PAM. 22 As reported below, PAM converted to the PAMNa form possessed a higher reactivity toward the OP compounds studied. It should be noted that upon reaching pH 8.6 in the aqueous solution of PAM in the process of the solution titration with minute quantities of sodium methoxide, the solution was snapfrozen in liquid nitrogen and dried under high vacuum, in a procedure designed to arrest possible degradation effects that are known to occur in aqueous alkaline solutions of PAM at elevated temperatures.…”

Section: ' Introductionmentioning

confidence: 75%

Montmorillonite Functionalized with Pralidoxime As a Material for Chemical Protection against Organophosphorous Compounds

Bromberg

Straut

Centrone

et al. 2011

ACS Appl. Mater. Interfaces

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Montmorillonite K-10 functionalized with α-nucleophilic 2-pralidoxime (PAM) and its zwitterionic oximate form (PAMNa) is introduced as a versatile material for chemical protection against organophosphorous (OP) compounds such as pesticides and chemical warfare agents (CWA). Upon inclusion into the montmorillonite interlayer structure, the pyridinium group of PAMNa is strongly physisorbed onto acidic sites of the clay, leading to shrinking of the interplanar distance. Degradation of diethyl parathion by PAMNa-functionalized montmorillonite in aqueous-acetonitrile solutions occurred primarily via hydrolytic conversion of parathion into diethylthio phosphoric acid, with the initial stages of hydrolysis observed to be pseudo-first-order reactions. Hydrolysis catalyzed by the clay intercalated by PAMNa was 10- and 17-fold more rapid than corresponding spontaneous processes measured at 25 and 70 °C, respectively. Hydrolytic degradation of diisopropyl fluorophosphate (DFP), a CWA simulant, was studied on montmorillonite clay functionalized by PAMNa and equilibrated with water vapor at 100% relative humidity by ³¹P high-resolution magic angle spinning NMR and was observed to be rather facile compared with the untreated montmorillonite, which did not show any DFP hydrolysis within 24 h. The incorporation of the functionalized clay particles into elastomeric film of polyisobutylene was shown to be a means to impart DFP-degrading capability to the film, with clay particle content exceeding 18 wt %.

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Section: ' Introductionmentioning

confidence: 75%

Montmorillonite Functionalized with Pralidoxime As a Material for Chemical Protection against Organophosphorous Compounds

Bromberg

Straut

Centrone

et al. 2011

ACS Appl. Mater. Interfaces

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“…Many cationic surfactants can also be used as micellar catalysts [18], able to accelerate chemical decomposition [19,20], and such compounds can find use as decontaminants for military purposes. Thus these properties are important in decontamination procedures for measuring the kinetics of cleavage of some model compounds such as organophosphates and others [21,22,23,24,25,26]. Many other properties of cationic surfactants were discovered.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Disinfection Effect of the Pyridine-4-aldoxime Based Salts

et al. 2015

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A set of new quaternary ammonium compounds based on pyridine-4-aldoxime was synthesized, characterized with analytical data (NMR, EA, HPLC, MS) and tested for in vitro antimicrobial activity (antibacterial, antifungal) and cytotoxicity. Quaternary pyridinium-4-aldoxime salts with length of alkyl side chain from C8 to C20 and belonging to the group of cationic surfactants were investigated in this work. An HPLC experimental protocol for characterization of mixtures of all homologues has been found. Antimicrobial evaluation found that yeast-type fungi were most sensitive towards C14 and C16 analogues, whereas the C16 analogue was completely ineffective against filamentous fungi. Antibacterial assessment showed versatility of C14 and relatively high efficacy of C16 OPEN ACCESSMolecules 2015, 20 3682 against G+ strains and C14 against G− strains. Notably, none of the studied compounds exceeded the efficacy and versatility of the benzalkonium C12 analogue, and benzalkonium analogues also exhibited lower cytotoxicity in the cell viability assay.

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“…Phosphines and other phosphorus‐containing compounds are used in a wide range of applications, including as ionic liquids, flame retardants, surfactants, and biocides . Our interest in the design and synthesis of phosphine‐functional polymers stems from the utility of phosphorus‐based functional groups in organic synthesis, for example, as stereoselective organocatalysts or as ligands in transition metal catalysis (e.g., Pd, Ru) .…”

Section: Introductionmentioning

confidence: 99%

Phosphorus‐Containing Gradient (Block) Copolymers via RAFT Polymerization and Postpolymerization Modification

Sykes

Harrisson

Keddie

2016

Macro Chemistry & Physics

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Reversible addition-fragmentation chain transfer (RAFT) copolymerization of styrene (St) and 4-(diphenylphosphino)styrene (DPPS) is explored to establish the statistical distribution of the phosphine-functional monomer within the copolymer. RAFT copolymerization of St and DPPS at a variety of feed ratios provides phosphine-functional copolymers of low dispersity at moderate monomer conversion (Ð <1.2 at conv. >60%). In all cases the fraction of DPPS in the resulting polymers is greater than that in the monomer feed. Estimation of copolymerization reactivity ratios indicates DPPS has a strong tendency to homopolymerize whilst St preferentially copolymerizes with DPPS (r DPPS = 4.4; r St = 0.31). The utility of the copolymers as macro-RAFT agents in block copolymer synthesis is demonstrated via chain extension with hydrophilic acrylamide (N,N-dimethylacrylamide (DMAm)) and acrylate a Supporting Information is available online from the Wiley Online Library or from the corresponding author.-2 -(poly(ethylene glycol) methyl ether acrylate (mPEGA); di(ethylene glycol) ethyl ether acrylate (EDEGA)) monomers. Finally access to polymers containing phosphine oxide and phosphonium salt functionalities is shown through post-polymerization modification of the phosphine-containing copolymers.

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Comparative study of nucleophilic efficacy of pralidoxime towards phosphorus, sulfur and thiophosphorus based esters

Cited by 9 publications

References 34 publications

Montmorillonite Functionalized with Pralidoxime As a Material for Chemical Protection against Organophosphorous Compounds

Montmorillonite Functionalized with Pralidoxime As a Material for Chemical Protection against Organophosphorous Compounds

Synthesis and Disinfection Effect of the Pyridine-4-aldoxime Based Salts

Phosphorus‐Containing Gradient (Block) Copolymers via RAFT Polymerization and Postpolymerization Modification

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