30-797: GS-7 [REDACTED] Names Other names S , S -dimethyl phosphoramidodithioate Identifiers 3D model ( JSmol ) Interactive image ChemSpider 16093132 PubChem CID 15151768 InChI InChI=1S/C2H8NOPS2/c1-6-5(3,4)7-2/h1-2H3,(H2,3,4) Key: BYWRZYACOWEUCQ-UHFFFAOYSA-N SMILES CSP(=O)(N)SC Properties Chemical formula C 2 H 8 N O P S 2 Molar mass 157.19 g·mol Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references Chemical compound GS-7
60-399: A = 41.6 × 10 . Phosphine reacts with water only at high pressure and temperature, producing phosphoric acid and hydrogen: Burning phosphine in the air produces phosphoric acid ): Phosphine may be prepared in a variety of ways. Industrially it can be made by the reaction of white phosphorus with sodium or potassium hydroxide , producing potassium or sodium hypophosphite as
90-453: A by-product. Alternatively, the acid-catalyzed disproportionation of white phosphorus yields phosphoric acid and phosphine. Both routes have industrial significance; the acid route is the preferred method if further reaction of the phosphine to substituted phosphines is needed. The acid route requires purification and pressurizing. It is prepared in the laboratory by disproportionation of phosphorous acid : Alternative methods are
120-460: A luminous flame. Phosphine is a highly toxic respiratory poison, and is immediately dangerous to life or health at 50 ppm. Phosphine has a trigonal pyramidal structure. Phosphines are compounds that include PH 3 and the organophosphines , which are derived from PH 3 by substituting one or more hydrogen atoms with organic groups. They have the general formula PH 3− n R n . Phosphanes are saturated phosphorus hydrides of
150-634: A wide range of chemical file formats , including Protein Data Bank (pdb), Crystallographic Information File (cif), MDL Molfile (mol), and Chemical Markup Language (CML). There is also a JavaScript -only ( HTML5 ) version, JSmol , that can be used on computers with no Java. The Jmol applet, among other abilities, offers an alternative to the Chime plug-in, which is no longer under active development. While Jmol has many features that Chime lacks, it does not claim to reproduce all Chime functions, most notably,
180-709: Is CH 3 , alkyl, etc. Phosphine is used as a dopant in the semiconductor industry, and a precursor for the deposition of compound semiconductors . Commercially significant products include gallium phosphide and indium phosphide . Phosphine is an attractive fumigant because it is lethal to insects and rodents, but degrades to phosphoric acid, which is non-toxic. As sources of phosphine, for farm use , pellets of aluminium phosphide (AlP), calcium phosphide ( Ca 3 P 2 ), or zinc phosphide ( Zn 3 P 2 ) are used. These phosphides release phosphine upon contact with atmospheric water or rodents' stomach acid. These pellets also contain reagents to reduce
210-463: Is 0.58 D, which increases with substitution of methyl groups in the series: CH 3 PH 2 , 1.10 D; (CH 3 ) 2 PH , 1.23 D; (CH 3 ) 3 P , 1.19 D. In contrast, the dipole moments of amines decrease with substitution, starting with ammonia , which has a dipole moment of 1.47 D. The low dipole moment and almost orthogonal bond angles lead to the conclusion that in PH 3
240-433: Is a colorless, flammable, highly toxic compound with the chemical formula P H 3 , classed as a pnictogen hydride . Pure phosphine is odorless, but technical grade samples have a highly unpleasant odor like rotting fish, due to the presence of substituted phosphine and diphosphane ( P 2 H 4 ). With traces of P 2 H 4 present, PH 3 is spontaneously flammable in air ( pyrophoric ), burning with
270-646: Is also likely to occur in other regions, but has not been as closely monitored. Genetic variants that contribute to high level resistance to phosphine have been identified in the dihydrolipoamide dehydrogenase gene. Identification of this gene now allows rapid molecular identification of resistant insects. Phosphine gas is denser than air and hence may collect in low-lying areas. It can form explosive mixtures with air, and may also self-ignite. Anne McCaffrey 's Dragonriders of Pern series features genetically engineered dragons that breathe fire by producing phosphine by extracting it from minerals of their native planet. In
300-14741: Is an organophosphorus anticholinesterase related to the organophosphate insecticide methamidophos . See also [ edit ] Tabun Dimefox Mipafox Schradan MSPI References [ edit ] ^ Mager, Peter P. (1984). Multidimensional pharmacochemistry : design of safer drugs . Orlando: Academic Press. p. 53. ISBN 978-0-12-465020-6 . ^ de Jong, Leo P. A.; Wolring, Gre Z.; Benschop, Hendrik P. (January 1982). "Reactivation of acetylcholinesterase inhibited by methamidophos and analogous (di)methylphosphoramidates". Archives of Toxicology . 49 (2): 175–183. doi : 10.1007/BF00332365 . PMID 7059283 . S2CID 19797252 . v t e Agents used in chemical warfare incapacitation riot control Blood agents Cyanogen Cyanogen bromide Cyanogen chloride (CK) Hydrogen cyanide (AC) Arsine Cacodyl cyanide Cacodyl oxide Hydrogen sulfide Phosphine Carbon monoxide Phosphorus trifluoride Methyl cyanoformate Iron pentacarbonyl Nickel tetracarbonyl 2,3,7,8-Tetrachlorodibenzodioxin Glycolonitrile Lactonitrile Acetone cyanohydrin Stibine Chloral cyanohydrin Blister agents Arsenicals Ethyldichloroarsine (ED) Methyldichloroarsine (MD) Phenyldichloroarsine (PD) Lewisite (L) Lewisite 2 (L2) Lewisite 3 (L3) Sulfur mustards Levinstein mustard (EA-229) T Q CEES Nitrogen mustards HN1 HN2 HN3 TL-301 Nettle agents Phosgene oxime (CX) Other KB-16 Dibutylchloromethyltin chloride Selenium oxychloride Nerve agents G-agents Tabun (GA) Sarin (GB) Chlorosarin (ClGB) Thiosarin (SGB) Soman (GD) Chlorosoman (ClGD) Ethylsarin (GE) GH Cyclosarin (GF) GP Fluorotabun EA-1356 EA-4352 Crotylsarin V-agents EA-2192 EA-3148 VE VG VM VP VR VS VX EA-1763 Chinese VX V-sub x (GD-7) GV agents GV (EA-5365) Novichok agents A-208 A-232 A-234 A-242 A-262 C01-A035 C01-A039 C01-A042 Carbamates Dimethylcarbamoyl fluoride EA-3887 EA-3887A EA-3966 EA-3990 EA-4056 T-1123 T-1152 T-1194 Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide) TL-599 TL-1238 TL-1299 TL-1317 Miotine (AR-28/T-1843) 3152 CT 4-686-293-01 (Agent 1-10) Other Diisopropyl fluorophosphate Dicyclohexyl phosphorofluoridate EA-2012 EA-2054 EA-2098 EA-2613 2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate Neopentylene fluorophosphate Selenophos Phospholine R-16661 Ro 3-0422 Methanesulfonyl fluoride Dimefox (TL-792) MSPI Precursors Acetonitrile AT ATO AlP A.P.C. complex Chlorosarin Chlorosoman Cyclohexanol 1,8-Dibromooctane N,N-Diisopropylaminoethanol (KB) EA-1250 DIHP ZS DEHP EA-1224 Dimethylamidophosphoric dichloride Dimethylamidophosphoric dicyanide DMHP Ethylphosphonoselenoic dichloride Formaldoxime Nital 4-Hydroxycoumarin Isopropyl alcohol (TB) Methyldichlorophosphine (SW) Methylphosphonyl difluoride (difluoro) (DF) Methylphosphonyl dichloride (dichloro) Nitromethane OPA mixture Phosphoryl chloride Phosphorus pentachloride Phosphorus trichloride (TH) Pinacolone Pinacolyl alcohol Phenacyl chloride QL 2,4,5-Trichlorophenol 3,3,5-Trimethylcyclohexanol Triethyl phosphite Trimethyl phosphite TC TG Neurotoxins Anatoxin-a Saxitoxin (TZ) Bungarotoxin Botulinum toxin (BTX) Tetanospasmin (TeNT) Ryanodine Ciguatoxin (CTX) Guanitoxin (GTX) Chlorophenylsilatrane Palytoxin (PTX) Maitotoxin (MTX) Tetrodotoxin Aconitine Brevetoxin (PbTX) Strychnine Antillatoxin (ATX) Tetraethyllead Dimethylmercury HN1 hydrochloride HN2 hydrochloride HN3 hydrochloride A-8564 Picrotoxin Sulfuryl fluoride Tremorine Oxotremorine Batrachotoxin Tetramethylenedisulfotetramine (TETS) Bicyclic phosphates IPTBO TBPO TBPS Cloflubicyne Trimethylolpropane phosphite Domoic acid Pulmonary/ choking agents Chlorine Bromine Phosgene (CG) Fluorine Perfluoroisobutene Chloropicrin (PS) Dimethyl(trifluoromethylthio)arsine Diphosgene (DP) Disulfur decafluoride (Z) Acrolein Ethyl bromoacetate Perchloromethyl mercaptan Phenylcarbylamine chloride Tetranitromethane Tetrachlorodinitroethane Chlorine trifluoride Perchloryl fluoride Cadmium oxide Cadmium chloride Mercuric chloride Selenium dioxide Selenoyl fluoride Trifluoronitrosomethane Trichloronitrosomethane Nitric oxide Nitrogen dioxide Dinitrogen tetroxide Sulfur dioxide Phosphorus trichloride Methyl isocyanate Ethenone Methyl vinyl ketone Trifluoroacetyl chloride Salcomine Fluomine Uranium hexafluoride Diborane Green Cross Vomiting agents Adamsite (DM) Chloropicrin Litharge - glycerine Diphenylchlorarsine Diphenylcyanoarsine Cacodyl cyanide o-Dianisidine Incapacitating agents BZ (CS-4030) Apomorphine Butyrophenone EA-4941 (CS-4640) Etorphine EA-2092 CS-4297 Etoxadrol Dimethylheptylpyran (DMHP) EA-2148 EA-3167 EA-3443 Pethidine EA-3580 Ibogaine EA-3834 Kolokol-1 LSD-25 PAVA spray Psilocybin Sleeping gas Carfentanil JB-318 JB-336 CS-27349 CAR-226,086 CAR-301,060 CAR-302,196 CAR-302,282 CAR-302,668 Benperidol Desflurane Enflurane Bufotenin Isoflurane Halothane Sevoflurane Pentazocine Procarbazine Fluphenazine Chlorpromazine Lachrymatory agents Xylyl bromide Pepper spray (OC) Mace (spray) CN CS CR CNS Benzyl chloride Benzyl bromide Benzyl iodide Bromobenzyl cyanide Thiophosgene Chloroacetone Bromoacetone Bromomethyl ethyl ketone Acrolein Phenacyl bromide Chloroacetophenone oxime Ethyl bromoacetate Ethyl iodoacetate Iodoacetone Allyl isothiocyanate Hexamethylene diisocyanate Crotonaldehyde DRC-5593 Malodorant agents Thioacetone Allicin Skatole Cadaverine Putrescine Cornea-clouding agents Lewisite CX KB-16 Methyl cyanoacrylate N-Methylmorpholine Allyl alcohol Osmium tetroxide Acrolein Biological toxins Abrin Aconitine Cyclopiazonic acid Histrionicotoxins Aflatoxins Anatoxin-a Batrachotoxin Botulinum toxin Brevetoxin Ciguatoxin Domoic acid Enterotoxin type B Grayanotoxin Guanitoxin Maitotoxin Modeccin Palytoxin Ricin Saxitoxin Shiga toxin T-2 mycotoxin Tetanospasmin Tetrodotoxin Volkensin Veratridine Other Methyl fluoroacetate Napalm (variants and mixtures) Fluoroethyl fluoroacetate Depleted uranium post-combustion uranium oxides Plutonium and its compounds Polonium White phosphorus List of chemical warfare agents CB military symbol v t e Acetylcholine metabolism and transport modulators Enzyme ( modulators ) ChAT Tooltip Choline acetyltransferase Inhibitors: 1-(-Benzoylethyl)pyridinium 2-(α-Naphthoyl)ethyltrimethylammonium 3-Chloro-4-stillbazole 4-(1-Naphthylvinyl)pyridine Acetylseco hemicholinium-3 Acryloylcholine AF64A B115 BETA CM-54,903 N,N-Dimethylaminoethylacrylate N,N-Dimethylaminoethylchloroacetate AChE Tooltip Acetylcholinesterase Inhibitors : Reversible: Carbamates: Aldicarb Aminocarb Bendiocarb Bufencarb Carbaryl Carbendazim Carbetamide Carbofuran Carbosulfan Chlorbufam Chloropropham Dimetilan Ethienocarb Ethiofencarb Fenobucarb Formetanate Formparanate Methiocarb Methomyl Metolcarb Miotine Oxamyl Phenmedipham Pinmicarb Pirimicarb Promecarb Propamocarb Propham Propoxur Thiodicarb Thiofanox ; Stigmines: Distigmine Eptastigmine Ganstigmine Neostigmine +glycopyrronium bromide Phenserine Physostigmine Pyridostigmine Quilostigmine Rivastigmine Terestigmine ; Others: Acotiamide Ambenonium Caffeine Donepezil EA-3990 EA-4056 Edrophonium Galantamine Huperzine A Huprine W Huprine X Huprine Y Ipidacrine Itopride Ladostigil Minaprine Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide) T-1123 T-1152 T-1194 TL-599 TL-1238 Tacrine Zanapezil Irreversible: Organophosphates: 2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate Acephate Armine Azinphos-ethyl Azinphos-methyl BAY-29952 Bensulide Cadusafos Carbophenothion Chlorethoxyfos Chlorfenvinphos Chlorpyrifos Chlorpyrifos-methyl Coumaphos Crotylsarin Cyanophos Cyclosarin (GF) Demephion Demeton Demeton-S-methyl Dialifor Diazinon Dichlorvos Dicrotophos Dicyclohexyl phosphorofluoridate Diisopropylphosphate Diisopropyl fluorophosphate Dimefox Dimethoate Dimethyl 4-(methylthio)phenyl phosphate Dioxathion Disulfoton EA-2012 EA-2054 EA-2098 EA-2192 EA-2613 EA-3148 EA-4352 Echothiophate Ethylsarin (GE) Endothion EPN Ethion Ethoprop Fenamiphos Fenitrothion Fenthion Fluorotabun Fonofos Formothion Fosthiazate GD-42 GH GT-45 GV Guanitoxin Hexaethyl tetraphosphate (HETP) Isofluorophate Isoxathion Leptophos Malaoxon Malathion Mazidox Methamidophos Methidathion Methyl phenkapton Methylfluorophosphonylcholine (MFPCh) Metrifonate Mevinphos Mipafox Monocrotophos MSPI Naled Novichok agent Omethoate Oxydemeton-methyl Paraoxon Parathion Parathion-methyl Phorate Phosalone Phosfolan Phosmet Phosphamidon Phoxim Pirimiphos-methyl Profenofos Prothoate R-16661 Ro 3-0340 Ro 3-0346 Ro 3-0347 Ro 3-0351 Ro 3-0352 Ro 3-0397 Ro 3-0411 Ro 3-0412 Ro 3-0417 Ro 3-0419 Ro 3-0422 Ro 3-0433 Ronnel Sarin (GB) Schradan Soman (GD) Sulfotep (TEDP) Tabun (GA) Tebupirimfos Temefos Terbufos Tetrachlorvinphos Tetraethyl pyrophosphate (TEPP) Triazofos Tribufos Trichlorfon Trichloronate Tricresyl phosphate VE VG VM VP VS VR VX ; Others: Demecarium Fasciculins (green mamba toxins) ( 1 , 2 , 3 , 4 ) Onchidal ( Onchidella binneyi ) Methanesulfonyl fluoride Unsorted: α-Pinene α-Viniferin Affinine Affinisine Arisugacin A Bulbocapnine Conodurine Coronaridine Corydaline Corynoline Crimidine Cyclanoline Cymserine Harmaline Kobophenol A Lactucopicrin Lycorine Phosacetim Rosmarinic acid Stercuronium iodide Taspine Tetrahydrocannabinol Ungeremine Ungiminorine Dimethylcarbamoyl fluoride BW284C51 TMTFA 3152 CT Reactivators : Asoxime chloride Methoxime Obidoxime Pralidoxime Trimedoxime bromide BChE Tooltip Butyrylcholinesterase Inhibitors: Affinine Affinisine Conodurine Cymserine Ladostigil Profenamine (ethopropazine) Rivastigmine Tacrine ZINC-12613047 Many of
330-443: Is computer software for molecular modelling chemical structures in 3-dimensions . Jmol returns a 3D representation of a molecule that may be used as a teaching tool, or for research e.g., in chemistry and biochemistry . Jmol is written in the programming language Java , so it can run on the operating systems Windows , macOS , Linux , and Unix , if Java is installed. It is free and open-source software released under
SECTION 10
#1732852428888360-565: Is heavier than air so it stays near the floor. Phosphine appears to be mainly a redox toxin, causing cell damage by inducing oxidative stress and mitochondrial dysfunction. Resistance in insects is caused by a mutation in a mitochondrial metabolic gene. Phosphine can be absorbed into the body by inhalation. The main target organ of phosphine gas is the respiratory tract. According to the 2009 U.S. National Institute for Occupational Safety and Health (NIOSH) pocket guide, and U.S. Occupational Safety and Health Administration (OSHA) regulation,
390-446: Is responsible for spontaneous flammability associated with PH 3 , and also for the characteristic orange/brown color that can form on surfaces, which is a polymerisation product. He considered diphosphine's formula to be PH 2 , and thus an intermediate between elemental phosphorus, the higher polymers, and phosphine. Calcium phosphide (nominally Ca 3 P 2 ) produces more P 2 H 4 than other phosphides because of
420-447: Is slight: 0.22 cm of gas dissolves in 1 cm of water. Phosphine dissolves more readily in non-polar solvents than in water because of the non-polar P−H bonds. It is technically amphoteric in water, but acid and base activity is poor. Proton exchange proceeds via a phosphonium ( PH + 4 ) ion in acidic solutions and via phosphanide ( PH − 2 ) at high pH, with equilibrium constants K b = 4 × 10 and K
450-685: Is strictly regulated due to high toxicity. Gas from phosphine has high mortality rate and has caused deaths in Sweden and other countries. Because the previously popular fumigant methyl bromide has been phased out in some countries under the Montreal Protocol , phosphine is the only widely used, cost-effective, rapidly acting fumigant that does not leave residues on the stored product. Pests with high levels of resistance toward phosphine have become common in Asia, Australia and Brazil. High level resistance
480-444: Is the increased resistance by insects. Deaths have resulted from accidental exposure to fumigation materials containing aluminium phosphide or phosphine. It can be absorbed either by inhalation or transdermally . As a respiratory poison, it affects the transport of oxygen or interferes with the utilization of oxygen by various cells in the body. Exposure results in pulmonary edema (the lungs fill with fluid). Phosphine gas
510-537: The GNU Lesser General Public License (LGPL) version 2.0. A standalone application and a software development kit (SDK) exist that can be integrated into other Java applications, such as Bioclipse and Taverna . A popular feature is an applet that can be integrated into web pages to display molecules in a variety of ways. For example, molecules can be displayed as ball-and-stick models , space-filling models , ribbon diagrams , etc. Jmol supports
540-537: The Sculpt mode. Chime requires plug-in installation and Internet Explorer 6.0 or Firefox 2.0 on Microsoft Windows , or Netscape Communicator 4.8 on Mac OS 9 . Jmol requires Java installation and operates on a wide variety of platforms. For example, Jmol is fully functional in Mozilla Firefox , Internet Explorer , Opera , Google Chrome , and Safari . Phosphine Phosphine ( IUPAC name: phosphane )
570-475: The atmosphere of Venus in quantities that could not be explained by known abiotic processes . Later re-analysis of this work showed interpolation errors had been made, and re-analysis of data with the fixed algorithm do not result in the detection of phosphine. The authors of the original study then claimed to detect it with a much lower concentration of 1 ppb. Phosphine is a precursor to many organophosphorus compounds . It reacts with formaldehyde in
600-478: The 8 hour average respiratory exposure should not exceed 0.3 ppm. NIOSH recommends that the short term respiratory exposure to phosphine gas should not exceed 1 ppm. The Immediately Dangerous to Life or Health level is 50 ppm. Overexposure to phosphine gas causes nausea, vomiting, abdominal pain, diarrhea, thirst, chest tightness, dyspnea (breathing difficulty), muscle pain, chills, stupor or syncope, and pulmonary edema. Phosphine has been reported to have
630-680: The P−H bonds are almost entirely pσ(P) – sσ(H) and phosphorus 3s orbital contributes little to the P-H bonding. For this reason, the lone pair on phosphorus is predominantly formed by the 3s orbital of phosphorus. The upfield chemical shift of it P NMR signal accords with the conclusion that the lone pair electrons occupy the 3s orbital (Fluck, 1973). This electronic structure leads to a lack of nucleophilicity in general and lack of basicity in particular (p K aH = –14), as well as an ability to form only weak hydrogen bonds . The aqueous solubility of PH 3
SECTION 20
#1732852428888660-413: The form P n H n +2 , such as triphosphane . Phosphine, PH 3 , is the smallest of the phosphines and the smallest of the phosphanes. Philippe Gengembre (1764–1838), a student of Lavoisier , first obtained phosphine in 1783 by heating white phosphorus in an aqueous solution of potash (potassium carbonate). Perhaps because of its strong association with elemental phosphorus , phosphine
690-486: The global phosphorus biochemical cycle . The most likely source is reduction of phosphate in decaying organic matter, possibly via partial reductions and disproportionations , since environmental systems do not have known reducing agents of sufficient strength to directly convert phosphate to phosphine. It is also found in Jupiter 's atmosphere. In 2020 a spectroscopic analysis was reported to show signs of phosphine in
720-470: The hydrolysis zinc phosphide : Some other metal phosphides could be used including aluminium phosphide , or calcium phosphide . Pure samples of phosphine, free from P 2 H 4 , may be prepared using the action of potassium hydroxide on phosphonium iodide : Phosphine is a worldwide constituent of the Earth's atmosphere at very low and highly variable concentrations. It may contribute significantly to
750-421: The odor of decaying fish or garlic at concentrations below 0.3 ppm. The smell is normally restricted to laboratory areas or phosphine processing since the smell comes from the way the phosphine is extracted from the environment. However, it may occur elsewhere, such as in industrial waste landfills. Exposure to higher concentrations may cause olfactory fatigue . Phosphine is used for pest control , but its usage
780-1697: The other AChE inhibitors listed above Transporter ( modulators ) CHT Tooltip Choline transporter Inhibitors: Hemicholinium-3 (hemicholine) Triethylcholine Enhancers: Coluracetam VAChT Tooltip Vesicular acetylcholine transporter Inhibitors: Vesamicol Release ( modulators ) Inhibitors SNAP-25 Tooltip Synaptosomal-associated protein 25 inactivators: Botulinum toxin ( A , C , E ) VAMP Tooltip Vesicle-associated membrane protein inactivators: Botulinum toxin ( B , D , F , G ) Others: Bungarotoxins ( β-bungarotoxin , γ-bungarotoxin ) Enhancers LPHN Tooltip Latrophilin agonists: α-Latrotoxin Others: Atracotoxins (e.g., robustoxin , versutoxin ) Crotoxin See also Receptor/signaling modulators Muscarinic acetylcholine receptor modulators Nicotinic acetylcholine receptor modulators Retrieved from " https://en.wikipedia.org/w/index.php?title=GS-7&oldid=1164200087 " Categories : Acetylcholinesterase inhibitors Methyl esters Phosphoramidodithioates Hidden categories: Chemical articles without CAS registry number Articles without InChI source Articles without EBI source Articles without KEGG source Articles without UNII source Articles containing unverified chemical infoboxes Articles with short description Short description matches Wikidata JSmol Jmol
810-435: The potential for ignition or explosion of the released phosphine. An alternative is the use of phosphine gas itself which requires dilution with either CO 2 or N 2 or even air to bring it below the flammability point. Use of the gas avoids the issues related with the solid residues left by metal phosphide and results in faster, more efficient control of the target pests. One problem with phosphine fumigants
840-491: The preponderance of P-P bonds in the starting material. The name "phosphine" was first used for organophosphorus compounds in 1857, being analogous to organic amines ( NR 3 ). The gas PH 3 was named "phosphine" by 1865 (or earlier). PH 3 is a trigonal pyramidal molecule with C 3 v molecular symmetry . The length of the P−H bond is 1.42 Å , the H−P−H bond angles are 93.5 ° . The dipole moment
870-470: The presence of hydrogen chloride to give tetrakis(hydroxymethyl)phosphonium chloride , which is used in textiles. The hydrophosphination of alkenes is versatile route to a variety of phosphines. For example, in the presence of basic catalysts PH 3 adds of Michael acceptors . Thus with acrylonitrile , it reacts to give tris(cyanoethyl)phosphine : Acid catalysis is applicable to hydrophosphination with isobutylene and related analogues: where R
900-476: Was once regarded as a gaseous form of the element, but Lavoisier (1789) recognised it as a combination of phosphorus with hydrogen and described it as phosphure d'hydrogène (phosphide of hydrogen). In 1844, Paul Thénard, son of the French chemist Louis Jacques Thénard , used a cold trap to separate diphosphine from phosphine that had been generated from calcium phosphide , thereby demonstrating that P 2 H 4
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