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Journal articles on the topic 'Organophosphorus compounds – Reactivity'

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Published: 4 June 2021

Last updated: 6 February 2022

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1

Tyryshkin, Nickolay I., Alexander I. Konovalov, Viktor V. Gavrilov, and Nina A. Polezhaeva. "Synthesis and Reactivity of New Organophosphorus Compounds." Phosphorus, Sulfur, and Silicon and the Related Elements 109, no. 1-4 (January 1996): 553–56. http://dx.doi.org/10.1080/10426509608545213.

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2

Li, Shu-Sen, and Cheng-Ye Yuan. "Studies on organophosphorus compounds 52. Structure-reactivity studies of organophosphorus compounds by MNDO calculations." Chinese Journal of Chemistry 10, no. 2 (August 27, 2010): 161–70. http://dx.doi.org/10.1002/cjoc.19920100210.

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3

Quan, Zheng-Jun, and Xi-Cun Wang. "The 2-phosphaethynolate anion: convenient synthesis and the reactivity." Org. Chem. Front. 1, no. 9 (2014): 1128–31. http://dx.doi.org/10.1039/c4qo00189c.

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4

Macarie, Lavinia, Nicoleta Plesu, Smaranda Iliescu, and Gheorghe Ilia. "Synthesis of organophosphorus compounds using ionic liquids." Reviews in Chemical Engineering 34, no. 5 (August 28, 2018): 727–40. http://dx.doi.org/10.1515/revce-2017-0014.

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Abstract Organophosphorus chemistry was developed in the last decade by promoting the synthesis reactions using ionic liquids either as solvent or catalyst. Ionic liquids (ILs), the so-called “green solvents”, have gained interest in the synthesis of organophosphorus compounds as alternatives to flammable and toxic organic solvents and catalysts. ILs have beneficial properties because they provide high solubility for many organic and inorganic compounds or metal complexes, have no vapor pressure, and are reusable. Also, in some cases, they can enhance the reactivity of chemical reagents. In this review, we aimed at showing the synthesis of different organophosphorus compounds under green and mild conditions using ILs as reaction media or catalysts, according to a trend developed in the last years. A novel trend is to perform these syntheses under microwave irradiation conditions together with ILs as solvents and catalysts.

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5

Galkin, Vladimir I., Artem A. Cherkasov, and Rafael A. Cherkasov. "New Methods for Quantitative Analysis of Organophosphorus Compounds Reactivity." Phosphorus, Sulfur, and Silicon and the Related Elements 177, no. 8-9 (August 2002): 2207. http://dx.doi.org/10.1080/10426500213326.

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6

TYRYSHKIN, N. I., A. I. KONOVALOV, V. V. GAVRILOV, and N. A. POLEZHAEVA. "ChemInform Abstract: Synthesis and Reactivity of New Organophosphorus Compounds." ChemInform 28, no. 11 (August 4, 2010): no. http://dx.doi.org/10.1002/chin.199711302.

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7

Yoshifuji, Masaaki. "Sterically protected organophosphorus compounds of unusual structures." Pure and Applied Chemistry 89, no. 3 (March 1, 2017): 281–86. http://dx.doi.org/10.1515/pac-2016-1029.

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AbstractThe character of bis(2,4,6-tri-tert-butylphenyl)diphosphene is described experimentally and theoretically. The diphosphene is stabilized by steric protection and the structure can be characterized by spectroscopic as well as crystallographic analyses. Theoretical calculation on the diphosphene strongly suggests that the P=P bond is an isolated double bond and that the P–C bonds are single covalent bond. The reactivity has been investigated including photolysis, oxidation, sulfurization, selenation, transition-metal complex formation, and carbene addition. Plausible mechanistic scheme for the reaction of the diphosphene with 3,4,5,6-tetrachlorocyclohexa-3,5-diene-1,2-dione (or tetrachloro-o-benzoquinone) to a pentavalent spiro product is discussed based on the product analysis.

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8

Popov, Anatoliy F. "Design of green microorganized systems for decontamination of ecotoxicants." Pure and Applied Chemistry 80, no. 7 (January 1, 2008): 1381–97. http://dx.doi.org/10.1351/pac200880071381.

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Due to population upsurge, pesticides (derivatives of organophosphorus acids included) find widespread use in agriculture. The toxicity and long-term environmental hazard of such compounds require detailed studies on decomposition mechanisms of the pesticides and development of efficient, readily available, and inexpensive systems for their decontamination. A simple and straightforward method for the decomposition of organophosphorus compounds involves their reactions with nucleophiles. Studies on the reactivity of "normal" and α-nucleophiles toward electron-deficient centers allowed us to state a number of basic principles on the nature of the α-effect. One of the most important conclusions is: It is unlikely that the structure variations in the known α-nucleophiles will result in higher reactivity than that of hydroxylamine anion. As a practical matter, the essential disadvantages of decomposition of organophosphorus compounds in water and organic solvents are: (i) instability of active nucleophiles and oxidizing agents, (ii) corrosiveness, and (iii) extremely low solubility of organophosphorus compounds in water. These dictate the strategy of further studies, namely, carrying out the reaction in microorganized media. The first research line involves the development of the functional imidazole-based detergents functionalized with α-nucleophilic fragments. A number of efficient detergents were first synthesized. An examination of the nucleophilicity of the functional fragments in water and in the micellar phase and quantitative assessment of the factors responsible for the micellar effects showed unambiguously that the main cause of the observed accelerations is the substrate concentrating in the micellar pseudophase. The second research line consists of studies on the reactivity of versatile oxidative/nucleophilic systems involving H2O2/activator and polyhalide ion organocomplexes in water, aqueous alcohols, and micelles of cationic detergents. The novel sources of "active" halogen are highly competitive both with conventional hazardous chlorine derivatives and "green" systems involving H2O2/activator.

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9

OKAJIMA, Toshiya, and Kaoru MAEGAWA. "Theoretical Study on the Reactivity for Hydrolysis of Organophosphorus Compounds." Journal of Environmental Chemistry 11, no. 3 (2001): 491–500. http://dx.doi.org/10.5985/jec.11.491.

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10

Yuan, Chengye, Shusen Li, and Shengang Yuan. "Computational and Theoretical Chemistry in Structure-Reactivity Studies of Organophosphorus Compounds." Phosphorus, Sulfur, and Silicon and the Related Elements 144, no. 1 (January 1, 1999): 765–68. http://dx.doi.org/10.1080/10426509908546357.

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11

Braga, Letícia S., Érika F. Silva, Daiana T. Mancini, Eduardo P. da Rocha, Elaine F. F. da Cunha, and Teodorico C. Ramalho. "Detection of Chemical Weapon Agents Using Spectroscopic Probes: A Computational Study." Journal of Chemistry 2020 (April 21, 2020): 1–11. http://dx.doi.org/10.1155/2020/1312403.

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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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12

Korzeniowska, Ewelina. "Synthesis of diphenylphosphinic acid esters." Annales Universitatis Mariae Curie-Sklodowska, sectio AA – Chemia 72, no. 1 (December 8, 2017): 23. http://dx.doi.org/10.17951/aa.2017.72.1.23.

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<p>The development of new methods for the synthesis of organophosphorus compounds is still an important part of organic chemistry due to the high demand for these compounds in organic synthesis as well as in asymmetric catalysis. Most of the methods for the synthesis of these compounds include the reactivity of the phosphorus atom, which depending on the structure might exhibit both electrophilic and nucleophilic properties. Herein, I will present the results concerning synthesis of diphenylphosphinic acid esters.</p>

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13

Ruf, Sven G., Jochen Dietz, and Manfred Regitz. "Organophosphorus Compounds. Part 151: Synthesis and Reactivity of a Novel Isophosphinoline Derivative." Tetrahedron 56, no. 34 (August 2000): 6259–67. http://dx.doi.org/10.1016/s0040-4020(00)00555-x.

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14

Mack, Andreas, Elke Pierron, Thomas Allspach, Uwe Bergsträßer, and Manfred Regitz. "Organophosphorus Compounds; 129. Mesitylphosphaacetylene: Synthesis and Reactivity Studies of a New Phosphaalkyne." Synthesis 1998, no. 09 (September 1998): 1305–13. http://dx.doi.org/10.1055/s-1998-6089.

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15

Shaov, Abubekir Kh, Asya N. Beslaneeva, Gennady B. Shustov, and Albina M. Altueva. "Study of the Nature of the Influence of some Oligophosphonates on the Rheological Properties of High-Density Polyethylene." Key Engineering Materials 899 (September 8, 2021): 606–12. http://dx.doi.org/10.4028/www.scientific.net/kem.899.606.

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High molecular weight compounds with organophosphorus backbones are usually obtained by polycondensation of phosphorus-containing monomers, leading, most often, to products of low molecular weight at low yields. This fact is explained [1] by several reasons: a decrease in the reactivity of the second functional group of the monomer after the first one has reacted; the possibility of the formation of cyclic compounds; hydrolytic instability of the phosphorus-heteroatom bond (usually P-O, P-N), etc.

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16

Cabal, J., J. Kassa, and J. Severa. "A comparison of the decontamination efficacy of foam-making blends based on cationic and nonionic tensides against organophosphorus compounds determinedin vitro and in vivo." Human & Experimental Toxicology 22, no. 9 (September 2003): 507–14. http://dx.doi.org/10.1191/0960327103ht377oa.

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The ability of foam-making blends to decontaminate the skin exposed to organophosphorus compounds was tested. The appropriate composition and rheological features (stability, grade of foaming) of tested blends were evaluated by in vitro methods and their ability to remove the contaminants from hard surface and to transform the contaminants into nontoxic compounds was evaluated byin vivo methods. The blends containing cationic and nonionic tensides as well as alkalized hydrogen peroxide seem to be the most efficacious to decontaminate the skin exposed to organophosphorus compounds according to the literature data. The composition of tested blends was optimized because particular components often have antagonistic effects. Cationic tensides support the reactivity of the blend and control the grade of foaming. Nonionic tensides control the stability of the foams but also react as retardants of the reactivity of the foams. Hydrogen peroxide is a real reacting component when it is transformed into hydrogen peroxide anion. It also acts as buffer if pH is higher than 11. Our in vivo results confirm that Desam OX (34 and 68%) and the foam-making blend containing benzalkonium chloride / Althosan MB (8%), Slovasol 2510 (2%) and hydrogen peroxide (3%) alkalized at pH 12 seem to be the most efficacious to remove contaminants (soman, VX) from the skin and transform them into nontoxic compounds. Therefore they could be used for primary decontamination of chemical casualties contaminated with nerve agents in the field condition.

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17

Yuan, Chengye, Shusen Li, and Shengang Yuan. "ChemInform Abstract: Computational and Theoretical Chemistry in Structure-Reactivity Studies of Organophosphorus Compounds." ChemInform 31, no. 9 (June 10, 2010): no. http://dx.doi.org/10.1002/chin.200009295.

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18

Asmus, Sven M. F., and Manfred Regitz. "Organophosphorus compounds. Part 163: Reactivity of phosphaalkynes towards in situ-generated titanium imido complexes." Tetrahedron Letters 42, no. 43 (October 2001): 7543–45. http://dx.doi.org/10.1016/s0040-4039(01)01351-x.

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19

Asmus, Sven M. F., Georg Seeber, Uwe Bergstraesser, and Manfred Regitz. "ChemInform Abstract: Organophosphorus Compounds. Part 158. A Study of the Reactivity of a Tetraphosphadeltacyclene." ChemInform 32, no. 44 (May 24, 2010): no. http://dx.doi.org/10.1002/chin.200144175.

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20

Peters, Christoph, Frank Tabellion, Anja Nachbauer, Uwe Fischbeck, Fritz Preuss, and Manfred Regitz. "Organophosphorus Compounds, Part 146* Imidovanadium(V) Complexes as Reaction Partners for Kinetically Stabilized Phosphaalkynes. Synthesis and Reactivity of 3-Aza-l,2,4,6-tetraphospha-quadricyclanes." Zeitschrift für Naturforschung B 56, no. 9 (September 1, 2001): 951–62. http://dx.doi.org/10.1515/znb-2001-0915.

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The Lewis base adducts of imidovanadium(V) compounds 5a,b undergo chemoselective cyclooligomerization reactions with the kinetically stabilized phosphaalkynes 4a-e to furnish the azatetraphosphaquadricyclanes 6a-f with incorporation of the imido fragment. The reactivity of this novel class of heteropolycyclic compounds has been examined exemplarily for compound 6a. Complexation of one and two phosphorus atoms was achieved by reaction with nonacarbonyldiiron or the tungsten pentacarbonyl-THF complex resulting in the formation of the transition metal compounds 17-20. Reactions of 6a with the sulfonyl azides 21ac furnished the Staudinger products 22a-c. The reaction of 6a with two equivalents of tosyl azide gave a surprising result. No double complexation leading to a symmetrical product was achieved, and compound 23 was obtained instead in which the two phosphorus atoms of one diphosphirane ring are functionalized. Oxidative cleavage of a P/P bond in 6a to furnish product 24 is observed in the reaction of 6a with the Lewis base-free imidovanadium(V) species 15a.

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21

Guerra, Fernanda, Mohamed Attia, Daniel Whitehead, and Frank Alexis. "Nanotechnology for Environmental Remediation: Materials and Applications." Molecules 23, no. 7 (July 18, 2018): 1760. http://dx.doi.org/10.3390/molecules23071760.

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Environmental remediation relies mainly on using various technologies (e.g., adsorption, absorption, chemical reactions, photocatalysis, and filtration) for the removal of contaminants from different environmental media (e.g., soil, water, and air). The enhanced properties and effectiveness of nanotechnology-based materials makes them particularly suitable for such processes given that they have a high surface area-to-volume ratio, which often results in higher reactivity. This review provides an overview of three main categories of nanomaterials (inorganic, carbon-based, and polymeric-based materials) used for environmental remediation. The use of these nanomaterials for the remediation of different environmental contaminants—such as heavy metals, dyes, chlorinated organic compounds, organophosphorus compounds, volatile organic compounds, and halogenated herbicides—is reviewed. Various recent examples are extensively highlighted focusing on the materials and their applications.

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22

Ruf, Sven G., Uwe Bergstraesser, and Manfred Regitz. "ChemInform Abstract: Organophosphorus Compounds. Part 145. Synthesis and Reactivity of a Polycyclic, Oxa-Bridged Phosphaalkene." ChemInform 32, no. 2 (January 9, 2001): no. http://dx.doi.org/10.1002/chin.200102174.

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23

MACK, A., E. PIERRON, T. ALLSPACH, U. BERGSTRAESSER, and M. REGITZ. "ChemInform Abstract: Organophosphorus Compounds. Part 129. Mesitylphosphaacetylene: Synthesis and Reactivity Studies of a New Phosphaalkyne." ChemInform 29, no. 50 (June 18, 2010): no. http://dx.doi.org/10.1002/chin.199850207.

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24

Baumgartner, Thomas, Petra Moors, Martin Nieger, Heike Hupfer, and Edgar Niecke. "Unusual Approaches to Organophosphorus Compounds: The Surprising Reactivity of Bis(methylene)phosphoranes and Related Phosphoranylidene Carbenoids." Organometallics 21, no. 23 (November 2002): 4919–26. http://dx.doi.org/10.1021/om020319n.

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25

Ginjaar, L., and S. Vel. "On the reactivity of organophosphorus compounds. I. The alkaline hydrolysis of some dialkyl p-nitrophenyl phosphates." Recueil des Travaux Chimiques des Pays-Bas 77, no. 10 (September 2, 2010): 956–62. http://dx.doi.org/10.1002/recl.19580771009.

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26

Lapshin, Ivan V., Alexander A. Kissel, and Alexander A. Trifonov. "Complexes of Rare- and Alkaline-Earth Elements in Catalytic Intermolecular Hydrophosphination of Multiple C—C Bonds." Vestnik RFFI, no. 2 (June 25, 2019): 58–73. http://dx.doi.org/10.22204/2410-4639-2019-102-02-58-73.

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In accordance with United Nations General Assembly resolution, the year 2019 was proclaimed the International Year of the Periodic Table of Chemical Elements. Rare-earth elements were discovered during the time of the Periodic System development. In the past few decades, their compounds have attracted great interest due to their unique reactivity. This review covers recent achievements in the field of intermolecular hydrophosphination of alkenes, dienes and alkynes, which is catalyzed by rare earth and alkaline-earth metal complexes. Catalytic hydrophosphination reaction is the addition of an P—H bond to С—С multiple bonds, and offers an efficient and elegant synthetic approach to production of the organophosphorus compounds widely used in industrial synthesis, pharmaceuticals, agrochemistry, and other areas. The high values of the ionic radii of rare earth and alkaline-earth metals in combination with the Lewis acidity provide their compounds with a pronounced tendency to complex formation and, accordingly, high coordination numbers. Due to high reactivity of M—E (E = C, H, N, P) bonds, ease of Ln—P ı-bond metathesis and multiple C—C bond insertions, these compounds offer new prospects for the catalysis of the alkenes and alkynes hydrophosphination. Therefore, complexes of non-toxic and relatively abundant in nature rare earth and alkaline earth metals can be a cheaper and more effective alternative to compounds of late transition metals in the catalysis of the C—P bond formation.

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27

Mack, Andreas, Uwe Bergstraesser, Guido J. Reiss, and Manfred Regitz. "ChemInform Abstract: Organophosphorus Compounds. Part 138. 3,5-Dimesityl-1,2,4-oxadiphosphole - Synthesis and Reactivity of a Novel Heterocycle." ChemInform 30, no. 28 (June 14, 2010): no. http://dx.doi.org/10.1002/chin.199928206.

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28

Smith, Rebecca L., Andreas Schweighofer, Helmut Keck, Wilhelm Kuchen, and Hilkka I. Kenttämaa. "Unusual Reactivity of the Radical Cations of Some Simple Trivalent Organophosphorus Compounds toward Dimethyl Disulfide and Dimethyl Diselenide." Journal of the American Chemical Society 118, no. 6 (January 1996): 1408–12. http://dx.doi.org/10.1021/ja9531182.

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29

van Hooidonk, C., G. W. Kraaij, and L. Ginjaar. "On the reactivity of organophosphorus compounds: Part IV. The alkaline hydrolysis of some O-phosphylated 2-pyridine oximes." Recueil des Travaux Chimiques des Pays-Bas 87, no. 6 (September 2, 2010): 673–86. http://dx.doi.org/10.1002/recl.19680870607.

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30

Popov, Anatolii, Illia Kapitanov, Anna Serdyuk, and Aleksandr Sumeiko. "REACTIVITY OF NUCLEOPHILES AND α-EFFECT IN SUBSTITUTION PROCESSES AT ELECTRON - DEFICIENCY CENTERS (Part 2)." Ukrainian Chemistry Journal 86, no. 8 (September 15, 2020): 77–100. http://dx.doi.org/10.33609/2708-129x.86.8.2020.77-100.

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The review analyzes issues related to the reactivity of nucleophiles and the manifestation of the α-effect in substitution processes at electron-deficient centers. The fundamental aspects of this phenomenon, as well as the possibilities and prospects of using α-nucleophiles in systems for the highly efficient degradation of substrates - ecotoxicants of various natures, are discussed. In the first part of the review such aspects were observed: inorganic α-nucleophiles as the most effective class of reagents for the decomposition of organic phosphorus compounds, hydroxylamine, its N-alkyl derivatives, oximes, and hydroxamic acids, reactivity of the НОО– anion in the processes of acyl group transfer, reactivity of oximate ions, inorganic α-nucleophiles as the basis of formulations for the degradation of neurotoxins, vesicants, and organophosphorus pesticides, design of inhibited acetylcholinesterase reactivators based on hydroxylamine derivatives, ways of structural modification of α-nucleophiles and systems based on them. The data on the reactivity of typical inorganic α-nucleophiles in the cleavage of acyl-containing substrates, including phosphorus acid esters, which provide abnormally high reaction rates in comparison with other supernucleophiles, are analyzed. Various types of such α-nucleophiles, features of their structure and reactivity are considered. It was shown that an important feature of hydroxylamine, oximes, and hydroxamic acids is the presence of a fragment with adjacent O and N (–N – O – H) atoms containing one or more lone electron pairs, which determines their belonging to the class of α-nucleophiles. It has been shown that a many of factors can be responsible for the manifestation of the α-effect and its magnitude, the main of which is the destabilization of the ground state of the nucleophile due to repulsion of lone electron pairs, stabilization of the transition state, the unusual thermodynamic stability of reaction products, solvation effects of the solvent, type of hybridization of the electrophilic center, etc.

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31

Lumbiny, Bilkis Jahan. "Effect of substituents on reactivity and reaction mechanism observed in Sn reaction of some organophosphorus compounds: based on Physical organic methodologies." Journal of the Asiatic Society of Bangladesh, Science 38, no. 1 (June 16, 2013): 17–27. http://dx.doi.org/10.3329/jasbs.v38i1.15317.

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The aminolyses of tetracoordinated organophosphorus compounds were investigated by varying substituents around phosphorus center or in nucleophile. The reactivity is expressed in terms of second-order rate constant, k2 and measured conductometrically. Physical organic chemistry tools; Hammett (?), Brönsted (?) LFER, CICs and heavy atom KIE have been used in quest for the mechanistic information. The pyridinolysis of O-aryl phenyl phosphonochloridothioates [PhP(=S)(OPh-Y)Cl, 1, and O,O-diphenyl Z-S-phenyl phosphorothiolates [(PhO)2P(=O)(S-Ph-Z)], 2, in acetonitrile at 35.0°C, were observed by varying substituents around phosphorus centre (Y in 1, Z in 2) or in nucleophile (X) and extended to pyridinolysis of 4-Chlorophenyl phenyl Chlorophosphate [4-ClPhOP(=O)(OPh)Cl], 3, in acetonitrile at 5.0°C (present study). The variation in X and Y in system 1 shows LFER with negative value of the Hammett coefficients, ?X, -(4.35 ~ 4.75), CICs, ?XY = ?0.46, which is in favour of concerted SN2 mechanism. The LFER plots obtained for 2 with the variation in X, with negative value of the ?X, -(4.43 ~ 4.76) indicating same mechanism as the system 1, substituent (Z) variations (log k2 vs. Z) are biphasic concave downwards with breaks at Z = H, ?XZ = ?0.70 for Z = electron donating group, ?XZ = +0.76 for Z = electron withdrawing group interpreting as the change in mechanism at Z = H from concerted to stepwise. In the light of the above reported results the LFER obtained for 3 with negative value of the ?X, -5.66 can be interpreted as SN2 process, with greater extent of bond formation in TS than that of 1, 2. DOI: http://dx.doi.org/10.3329/jasbs.v38i1.15317 J. Asiat. Soc. Bangladesh, Sci. 38(1): 17-27, June 2012

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32

Lumbiny, Bilkis Jahan, Zhang Hui, and M. Azizul Islam. "Influence of Substituents on Reactivity and Reaction Mechanism of SN Reaction of Some Organophosphorus Compounds; Relied on Linear Free Energy Relationship." APCBEE Procedia 9 (2014): 42–47. http://dx.doi.org/10.1016/j.apcbee.2014.01.008.

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33

Vasylenko, Volodymyr, Marina Sidorenko, and Saulius Mickevičius. "Industrial method of decontamination of dimethoate containing wastewater." E3S Web of Conferences 265 (2021): 04002. http://dx.doi.org/10.1051/e3sconf/202126504002.

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The problem of wastewater disposal affects not only third countries, but also world giants such as China or the United States of America. The European Union and the Commonwealth of Independent States are no exception. The increasing use of organophosphate pesticides requires the search for new, more efficient and cheaper ways to dispose of their residual amounts. The existing methods of disposal of toxic waste are costly, ineffective, and environmentally hazardous. The optimal solution can be a chemical system for decontamination of wastewater directly at the place of their origin, for example, at the production of pesticide formulations and agro-industrial facilities. This article presents the results of studying the effectiveness of the chemical system for the destruction of organophosphorus compounds based on hydrogen peroxide and potassium hydroxide in relation to dimethoate. The results of the scaling of the decontamination process are presented and an installation for the technological process of wastewater disposal is proposed. The research results show a high reactivity of the system under study and a high efficiency level of the described technological process.

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34

de Castro, Alexandre A., Daniel A. Polisel, Bruna T. L. Pereira, Elaine F. F. da Cunha, Kamil Kuca, Eugenie Nepovimova, and Teodorico C. Ramalho. "Understanding the Interaction Modes and Reactivity of Trimedoxime toward MmAChE Inhibited by Nerve Agents: Theoretical and Experimental Aspects." International Journal of Molecular Sciences 21, no. 18 (September 5, 2020): 6510. http://dx.doi.org/10.3390/ijms21186510.

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Organophosphorus (OP) compounds are used as both chemical weapons and pesticides. However, these agents are very dangerous and toxic to humans, animals, and the environment. Thus, investigations with reactivators have been deeply developed in order to design new antidotes with better efficiency, as well as a greater spectrum of action in the acetylcholinesterase (AChE) reactivation process. With that in mind, in this work, we investigated the behavior of trimedoxime toward the Mus musculus acetylcholinesterase (MmAChE) inhibited by a range of nerve agents, such as chemical weapons. From experimental assays, reactivation percentages were obtained for the reactivation of different AChE–OP complexes. On the other hand, theoretical calculations were performed to assess the differences in interaction modes and the reactivity of trimedoxime within the AChE active site. Comparing theoretical and experimental data, it is possible to notice that the oxime, in most cases, showed better reactivation percentages at higher concentrations, with the best result for the reactivation of the AChE–VX adduct. From this work, it was revealed that the mechanistic process contributes most to the oxime efficiency than the interaction in the site. In this way, this study is important to better understand the reactivation process through trimedoxime, contributing to the proposal of novel antidotes.

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35

Asmus, Sven M. F. "Organophosphorus Compounds; 142: A Simple Approach to 1,2,4-Selena- and Telluradiphospholes from Phosphaalkynes and the Chalcogen Elements and a First Study of their Reactivity." Synthesis 1999, no. 09 (September 1999): 1642–50. http://dx.doi.org/10.1055/s-1999-3573.

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36

Ginjaar, L., and S. Blasse-Vel. "On the reactivity of organophosphorus compounds: II. The effects of structural variations in the alkyl and alkoxy groups on the values of ΔH* and ΔS* for the alkaline hydrolysis of a number of organophosphorus esters." Recueil des Travaux Chimiques des Pays-Bas 85, no. 7 (September 2, 2010): 694–700. http://dx.doi.org/10.1002/recl.19660850706.

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37

MACKEWITZ, T. W., C. PETERS, U. BERGSTRAESSER, S. LEININGER, and M. REGITZ. "ChemInform Abstract: Contribution to Organophosphorus Compounds. Part 120. Phosphaalkenes as Building Blocks in Ene Reactions: Synthesis and Reactivity of 3-Amino-1,2-dihydro-1,2-diphosphetes." ChemInform 29, no. 12 (June 23, 2010): no. http://dx.doi.org/10.1002/chin.199812147.

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38

Asmus, Sven M. F., Uwe Bergstraesser, and Manfred Regitz. "ChemInform Abstract: Organophosphorus Compounds. Part 142. A Simple Approach to 1,2,4-Selena- and Telluradiphospholes from Phosphaalkynes and the Chalcogen Elements and a First Study of Their Reactivity." ChemInform 30, no. 49 (June 12, 2010): no. http://dx.doi.org/10.1002/chin.199949158.

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39

Francis, Matthew D., Peter B. Hitchcock, John F. Nixon, and László Nyulászi. "Reactivity of [M(η4-P2C2tBu2)] (M = Ge, Sn), withtert-Butylphosphaethyne P≡CtBu: Synthesis, Structural Characterisation and Computational Studies of the Novel Zwitterionic Organophosphorus Cage Compounds [MP4C4tBu4] (M = Ge, Sn)." European Journal of Inorganic Chemistry 2008, no. 11 (April 2008): 1761–66. http://dx.doi.org/10.1002/ejic.200700915.

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40

Jończyk, Jakub, Jędrzej Kukułowicz, Kamil Łątka, Barbara Malawska, Young-Sik Jung, Kamil Musilek, and Marek Bajda. "Molecular Modeling Studies on the Multistep Reactivation Process of Organophosphate-Inhibited Acetylcholinesterase and Butyrylcholinesterase." Biomolecules 11, no. 2 (January 27, 2021): 169. http://dx.doi.org/10.3390/biom11020169.

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Poisoning with organophosphorus compounds used as pesticides or misused as chemical weapons remains a serious threat to human health and life. Their toxic effects result from irreversible blockade of the enzymes acetylcholinesterase and butyrylcholinesterase, which causes overstimulation of the cholinergic system and often leads to serious injury or death. Treatment of organophosphorus poisoning involves, among other strategies, the administration of oxime compounds. Oximes reactivate cholinesterases by breaking the covalent bond between the serine residue from the enzyme active site and the phosphorus atom of the organophosphorus compound. Although the general mechanism of reactivation has been known for years, the exact molecular aspects determining the efficiency and selectivity of individual oximes are still not clear. This hinders the development of new active compounds. In our research, using relatively simple and widely available molecular docking methods, we investigated the reactivation of acetyl- and butyrylcholinesterase blocked by sarin and tabun. For the selected oximes, their binding modes at each step of the reactivation process were identified. Amino acids essential for effective reactivation and those responsible for the selectivity of individual oximes against inhibited acetyl- and butyrylcholinesterase were identified. This research broadens the knowledge about cholinesterase reactivation and demonstrates the usefulness of molecular docking in the study of this process. The presented observations and methods can be used in the future to support the search for new effective reactivators.

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41

Mohamed, Rauda A., Keat K. Ong, Noor Azilah M. Kasim, Norhana A. Halim, Siti Aminah M. Noor, Victor F. Knight, Nurul Najwa Ab. Rahman, and Wan Md Zin W. Yunus. "Transitioning from Oxime to the Next Potential Organophosphorus Poisoning Therapy Using Enzymes." Journal of Chemistry 2021 (August 20, 2021): 1–16. http://dx.doi.org/10.1155/2021/7319588.

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For years, organophosphorus poisoning has been a major concern of health problems throughout the world. An estimated 200,000 acute pesticide poisoning deaths occur each year, many in developing countries. Apart from the agricultural pesticide poisoning, terrorists have used these organophosphorus compounds to attack civilian populations in some countries. Recent misuses of sarin in the Syrian conflict had been reported in 2018. Since the 1950s, the therapy to overcome this health problem is to utilize a reactivator to reactivate the inhibited acetylcholinesterase by these organophosphorus compounds. However, many questions remain unanswered regarding the efficacy and toxicity of this reactivator. Pralidoxime, MMB-4, TMB-4, obidoxime, and HI-6 are the examples of the established oximes, yet they are of insufficient effectiveness in some poisonings and only a limited spectrum of the different nerve agents and pesticides are being covered. Alternatively, an option in the treatment of organophosphorus poisoning that has been explored is through the use of enzyme therapy. Organophosphorus hydrolases are a group of enzymes that look promising for detoxifying organophosphorus compounds and have recently gained much interest. These enzymes have demonstrated remarkable protective and antidotal value against some different organophosphorus compounds in vivo in animal models. Apart from that, enzyme treatments have also been applied for decontamination purposes. In this review, the restrictions and obstacles in the therapeutic development of oximes, along with the new strategies to overcome the problems, are discussed. The emerging interest in enzyme treatment with its advantages and disadvantages is described as well.

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42

Polimbetova, G. S., M. M. Aleshkova, G. O. Bugubaeva, Zh U. Ibraimova, and A. K. Borangazieva. "Oxidation of Sodium Hypophosphite by Oxygen in Alcoholic Solutions of Ferrum (III)." Eurasian Chemico-Technological Journal 7, no. 1 (September 21, 2016): 33. http://dx.doi.org/10.18321/ectj410.

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<p>Hypophosphites are widely used as reducers in the metal protection coating, as reagents in the synthesis of various organophosphorus compounds, in analytical chemistry, and in many other fields. NaH<sub>2</sub>PO<sub>2</sub> difficultly reacts with many oxidizers without catalysts despite of the significant reduction potential. The kinetics and the mechanism of hypophosphite oxidation in aqueous acid solution of the metal and nonmetal salts are studied in detail. The reactivity of hypophosphite in the organic solvents was not almost studied. In this work the basic possibility of synthesis dialkylphosphites from cheap, accessible and harmless NaH<sub>2</sub>PO<sub>2</sub> and alcohols is shown. Sodium hypophosphite is oxidized by oxygen in alcoholic solutions of FeCl<sub>3</sub> at 50-80 °С to dialkylphosphites. Kinetic and mechanism of the reaction are investigated by methods of volumetry, redox-potentiometry, GC, IR-, UV-, EPR-, Mössbauer- and NMR <sup>31</sup>Р-spectroscopy and X-ray powder diffraction analysis, optimum conditions are found, kinetic and activation parameters of the reaction are calculated. It is shown, that the process follows redox-mechanism and consists of two key stages: reduction of Fe (III) by hypophosphite with formation of dialkylphosphite and reoxidation of Fe (II) by oxygen. The coordination mechanism of reduction reaction of Fe (III) by hypophosphite is proposed. According to this mechanism the dialkylphosphite forms through innersphere redox-decomposition of intermediate alcoxyhypophosphite complex of Fe (III). The coordination mechanism of the process is confirmed by low values of Е<sup>≠</sup> and negative activation entropies ∆S<sup>≠</sup>. The availability in an inner sphere of Fe (III) bromide, low-molecular alcohols, water, characterized by high acidity, increases the reaction rate of oxidative alcoxylation of hypophosphite and promotes the further transformation of dialkylphosphite to di- and trialkylphosphate.</p>

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43

Francis, Matthew D., Peter B. Hitchcock, John F. Nixon, and László Nyulászi. "Reactivity of [M(η4-P2C2tBu2)] (M = Ge, Sn), withtert-Butylphosphaethyne P≡CtBu: Synthesis, Structural Characterisation and Computational Studies of the Novel Zwitterionic Organophosphorus Cage Compounds [MP4C4tBu4] (M = Ge, Sn) (Eur. J. Inorg. Chem. 11/2008)." European Journal of Inorganic Chemistry 2008, no. 11 (April 2008): 1735. http://dx.doi.org/10.1002/ejic.200890026.

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44

Malinak, David, Eugenie Nepovimova, Daniel Jun, Kamil Musilek, and Kamil Kuca. "Novel Group of AChE Reactivators—Synthesis, In Vitro Reactivation and Molecular Docking Study." Molecules 23, no. 9 (September 7, 2018): 2291. http://dx.doi.org/10.3390/molecules23092291.

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The acetylcholinesterase (AChE) reactivators (e.g., obidoxime, asoxime) became an essential part of organophosphorus (OP) poisoning treatment, together with atropine and diazepam. They are referred to as a causal treatment of OP poisoning, because they are able to split the OP moiety from AChE active site and thus renew its function. In this approach, fifteen novel AChE reactivators were determined. Their molecular design originated from former K-oxime compounds K048 and K074 with remaining oxime part of the molecule and modified part with heteroarenium moiety. The novel compounds were prepared, evaluated in vitro on human AChE (HssAChE) inhibited by tabun, paraoxon, methylparaoxon or DFP and compared to commercial HssAChE reactivators (pralidoxime, methoxime, trimedoxime, obidoxime, asoxime) or previously prepared compounds (K048, K074, K075, K203). Some of presented oxime reactivators showed promising ability to reactivate HssAChE comparable or higher than the used standards. The molecular modelling study was performed with one compound that presented the ability to reactivate GA-inhibited HssAChE. The SAR features concerning the heteroarenium part of the reactivator’s molecule are described.

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Lima, Joselia A., Laura P. A. N. Cavalcanti, Alcino P. Aguiar, Claudia M. Rezende, Keila S. C. Lima, and Antonio L. S. Lima. "In vitro evaluation of neutral oximes as reactivators of parathion-inhibited electric eel acetylcholinesterase." Defence Life Science Journal 2, no. 3 (August 3, 2017): 363. http://dx.doi.org/10.14429/dlsj.2.10723.

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<p>Organophosphorus (OP) compounds are irreversible inhibitors of acetylcholinesterase (AChE) commonly used as pesticides and, unfortunately, as nerve agents in terrorist attacks. These compounds are highly soluble easily crossing the blood-brain barrier (BBB). Clinically, oximes such as pralidoxime and obidoxime are used for the reactivation of AChE. These oximes are not sufficiently effective to reactivate AChE inhibited by different OPs besides the fact that they are permanently charged and do not readily cross the BBB. This work evaluated the ability of ten neutral oximes to reactivate parathion-inhibited eel AChE. Because oximes can bind to AChE as reversible inhibitors, this property was also evaluated, with pralidoxime (2-PAM) used as a reference compound. Unlike 2-PAM, which inhibited AChE in a concentration-dependent manner, neutral oximes were not good inhibitors of AChE. Neutral ligands can present affinity for the PAS site. Neutral oximes 1 and 2 (200 mM) reactivated parathion-inhibited eel AChE by 9% and 11%, respectively; but neither of them surpassed the reactivation efficacy of 2-PAM (25%). Neutral oximes 1 and 2 reactivated AChE at a safe concentration for humans. Both neutral oximes 1 and 2 are good non-quaternary moieties for the synthesis of conjugates with enhanced reactivation potency and BBB penetration.</p>

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46

Borowski, Piotr, Marek Stankevič, Dorota Strzelecka, and Olga Bąk. "Dynamic Kinetic Resolution of Phosphinic Acid Derivatives via Nucleophilic Substitution at Phosphorus Center." Synthesis 50, no. 24 (September 5, 2018): 4922–32. http://dx.doi.org/10.1055/s-0037-1609947.

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Reaction of racemic phosphinic acid derivatives with chiral alcohols proceeds with predominant formation of one diastereomer. The highest level of enrichment has been obtained for transesterfication of racemic methyl benzylphenylphosphinate (64% de). The outcome of the reaction depends on both the structure of chiral alcohol and the starting organophosphorus compound. The results strongly suggest that the nature of the observed phenomena is not a classical equilibration of intermediates found in dynamic kinetic resolution process but is a result of a different reactivity of both enantiomers of racemic substrate towards the same chiral nucleophile.

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47

Bušić, Valentina, Maja Katalinić, Goran Šinko, Zrinka Kovarik, and Dajana Gašo-Sokač. "Pyridoxal oxime derivative potency to reactivate cholinesterases inhibited by organophosphorus compounds." Toxicology Letters 262 (November 2016): 114–22. http://dx.doi.org/10.1016/j.toxlet.2016.09.015.

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48

Thakur, Ashima, Pooja Patil, Abha Sharma, and S. J. S. Flora. "Advances in the Development of Reactivators for the Treatment of Organophosphorus Inhibited Cholinesterase." Current Organic Chemistry 24, no. 24 (December 31, 2020): 2845–64. http://dx.doi.org/10.2174/1385272824999201020203544.

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Abstract:: Organophosphorus Compounds (OPCs) are used as pesticides to control pest, as chemical weapons in military conflict and unfortunately in the terrorist attack. These compounds are irreversible inhibitors of acetylcholinesterase, resulting in the accumulation of acetylcholine that leads to severe health complications which may be ended with the death of the victim. Current antidotes used for reactivation of organophosphorus inhibited acetylcholinesterase (OP-AChE) are not able to cross the blood-brain barrier efficiently, therefore being incapable to reactivate OP-AChE of the central nervous system. Due to limitations with current antidotes, there is an urgent need for new effective antidotes that could be included in the treatment regimen of OP poisoning. In this direction, comprehensive work has been done to improve the permeability of existing antidotes using a variety of strategies that include synthesis of oxime bonded to peripheral site binding moiety via an alkyl, aryl, or heteroatom-containing linker, synthesis of sugar oximes, and prodrug of 2-PAM, incorporating fluorine and chlorine in the structure of charged oximes. Other classes of compounds such as the mannich base, N-substituted hydroxyimino acetamide, alkylating agents, have been investigated for reactivation of OP-AChE. This review comprises the development of various classes of reactivators with the aim of either enhancing blood-brain permeability of existing antidotes or discovering a new class of reactivators.

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Calas, André-Guilhem, Anne-Sophie Hanak, Nina Jaffré, Aurélie Nervo, José Dias, Catherine Rousseau, Charlotte Courageux, et al. "Efficacy Assessment of an Uncharged Reactivator of NOP-Inhibited Acetylcholinesterase Based on Tetrahydroacridine Pyridine-Aldoxime Hybrid in Mouse Compared to Pralidoxime." Biomolecules 10, no. 6 (June 4, 2020): 858. http://dx.doi.org/10.3390/biom10060858.

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(1) Background: Human exposure to organophosphorus compounds employed as pesticides or as chemical warfare agents induces deleterious effects due to cholinesterase inhibition. One therapeutic approach is the reactivation of inhibited acetylcholinesterase by oximes. While currently available oximes are unable to reach the central nervous system to reactivate cholinesterases or to display a wide spectrum of action against the variety of organophosphorus compounds, we aim to identify new reactivators without such drawbacks. (2) Methods: This study gathers an exhaustive work to assess in vitro and in vivo efficacy, and toxicity of a hybrid tetrahydroacridine pyridinaldoxime reactivator, KM297, compared to pralidoxime. (3) Results: Blood–brain barrier crossing assay carried out on a human in vitro model established that KM297 has an endothelial permeability coefficient twice that of pralidoxime. It also presents higher cytotoxicity, particularly on bone marrow-derived cells. Its strong cholinesterase inhibition potency seems to be correlated to its low protective efficacy in mice exposed to paraoxon. Ventilatory monitoring of KM297-treated mice by double-chamber plethysmography shows toxic effects at the selected therapeutic dose. This breathing assessment could help define the No Observed Adverse Effect Level (NOAEL) dose of new oximes which would have a maximum therapeutic effect without any toxic side effects.

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50

Katagi, Manjunatha S., Jennifer Fernandes, Shivalingrao Mamledesai, Sujatha M.L., Rekha A., and Girish Bolakatti. "Schiff Base Oxime Derivatives Reactivate Chlorpyrifos-induced Acetylcholinesterase Inhibition." INNOSC Theranostics and Pharmacological Sciences 2, no. 1 (July 2, 2019): 12–16. http://dx.doi.org/10.26689/itps.v2i1.499.

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Background: The biological effects of organophosphorus (OP) compounds are connected with the irreversible inhibition of acetylcholinesterase (AChE), an important neuromediator acetylcholine (ACh) splitting enzyme in the human body at the synaptic clefts. Due to this inhibition, AChE is unable to fulfil its physiological function resulting in the accumulation of ACh, which, in turn over stimulates the parasympathetic nerve receptors, and causes fatal cholinergic crisis. Objective: The objective of the study was to synthesize a series of Schiff base oximes and to assess their evaluating for their in vitro reactivating potency against chlorpyrifos inhibited AChE. Methods: The amino group of 4-amino acetophenone exploited by treating with substituted benzaldehyde in the presence of glacial acetic acid to form Schiff base (1a-1f). The titled compounds (2a-2f) were prepared by treating Schiff base with hydroxylamine hydrochloride in the presence of alcohol. Through structural and spectral analysis, the structure of compounds was confirmed. The synthesized compounds were evaluated for their reactivation efficacy against chlorpyrifos-inhibited rat brain AChE by Ellman's method. Results: The pralidoxime (2-PAM) was potent reactivation against chlorpyrifos-inhibited AChE at the concentration tested (0.001 M). In this case, the compounds 2a (40.4%, 60 min) and 2d (37.9%, 60 min) showed promising reactivation as compared to 2-PAM (40.6%, 60min) against chlorpyrifos-inhibited AChE. Conclusion: Compounds having chloro (2a) and nitro (2d) substitution on 4th position gave good activity against chlorpyrifos-inhibited AChE. Moreover, these Schiff base oximes seem to be very promising because of their sufficient reactivation strength at lower concentration (10-3 M).

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