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Chemical compound hydrogen phosphide
Phosphine (IUPAC name: phosphane) is a colorless, flammable, highly toxic compound with the chemical formula PH3, classed as a pnictogen hydride. Pure
Phosphine
Scientific assessments on the microbial habitability of Venus
September 2020, research was published that reported the presence of phosphine in the planet's atmosphere, a potential biosignature. However, doubts
Life_on_Venus
Organic compound with at least one covalent carbon–phosphorus bond
by their coordination number σ and their valency λ. In this system, a phosphine is a σ3λ3 compound. Phosphate esters have the general structure P(=O)(OR)3
Organophosphorus_chemistry
In chemistry, phosphine-boranes are organophosphorus compounds with the formula R3−nHnPBH3. They are Lewis acid-Lewis base adducts derived from organophosphines
Phosphine-borane
analogous to phosphine oxides, phosphine sulfides, and phosphine selenides. Unlike other members of this series, the phosphine tellurides are labile with
Phosphine_telluride
Class of chemical compounds
An inorganic phosphine oxide is phosphoryl chloride (POCl3). The parent phosphine oxide (H3PO) remains rare and obscure. Tertiary phosphine oxides are the
Phosphine_oxides
Chemical compound
Phosphine oxide is the inorganic compound with the formula H3PO. Although stable as a dilute gas, liquid or solid samples are unstable. Unlike many other
Phosphine_oxide
Chemical compounds containing phosphorus and metals
A metal-phosphine complex is a coordination complex containing one or more phosphine ligands. Almost always, the phosphine is an organophosphine of the
Metal-phosphine_complex
tertiary phosphine sulfide is triphenylphosphine sulfide. Phosphine sulfides are sometimes intermediates in the synthesis of tertiary phosphines. Phosphine sulfides
Phosphine_sulfide
Chemical reaction for synthesizing C–N bonds
catalyst systems. The following years saw development of more sophisticated phosphine ligands that allowed extension to a larger variety of amines and aryl
Buchwald–Hartwig_amination
Gas layer surrounding Venus
discussion regarding whether phosphine (PH3) might be present in trace amounts in Venus's atmosphere. This would be noteworthy as phosphine is a potential biomarker
Atmosphere_of_Venus
Chemical compounds with at least one palladium atom
respectively. Many other more exotic ligands form a large variety of palladium-phosphine catalysts, such as 1,1'-bis(diphenylphosphino)ferrocene (dppf) to form
Palladium_compounds
Chemical compound
TCEP (tris(2-carboxyethyl)phosphine) is a reducing agent frequently used in biochemistry and molecular biology applications. It is often prepared and
TCEP
Class of chemical compounds
Transition metal complexes of phosphine oxides are coordination complex containing one or more phosphine oxide ligands. Many phosphine oxides exist and most behave
Transition metal complexes of phosphine oxides
Transition_metal_complexes_of_phosphine_oxides
Chemical compound
Tris(trimethylsilyl)phosphine is the organophosphorus compound with the formula P(SiMe3)3 (Me = methyl). It is a colorless liquid that ignites in air
Tris(trimethylsilyl)phosphine
Iminophosphoranes (also known as phosphine imides, phosphinimide, phosphinimines, λ5-phosphazenes, acyclic phosphazenes) are a class of organophosphorus
Iminophosphorane
Chemical compound
Tris(cyanoethyl)phosphine is the organophosphorus compound with the formula P(CH2CH2CN)3. It is white solid that is air stable, which is unusual for a
Tris(cyanoethyl)phosphine
Chemical compound
acids are deoxygenated with DIBAH. The resulting secondary phosphines are precursors to phosphine ligands. Saunders, Jeffrey O.; Wang, Zheng; Ding, Kuiling
Diphenylphosphine_oxide
Chemical compound
rearrangement, intramolecular nucleophilic addition of the new alkyl phosphine to the carbocation, and oxidation of the resulting phosphetanium with
Phosphetane
Chemical compound
Tris(dimethylamino)phosphine is an organophosphorus compound with the formula P(NMe2)3 (Me = methyl). It is a colorless oil at room temperature, and is
Tris(dimethylamino)phosphine
Chemical compounds with the structure R–O–O–R'
Phosphodiester Phosphonate Phosphite Phosphonous Phosphinate Phosphine oxide Phosphine Phosphonium Phosphaalkene Phosphaalkyne Phosphaallene Arsenic
Peroxide
Class of chemical compounds
classified according to the value of n: primary phosphines (n = 1), secondary phosphines (n = 2), tertiary phosphines (n = 3). All adopt pyramidal structures
Organophosphine
Chemical compound
organic synthesis. HMPA is the oxide of tris(dimethylamino)phosphine, P(NMe2)3. Like other phosphine oxides (such as triphenylphosphine oxide), the molecule
Hexamethylphosphoramide
a tertiary phosphine occurs with barriers near 30 kcal/mol. Thus, chiral arsines are more configurationally stable than chiral phosphines. The As-C bond
Transition metal arsine complexes
Transition_metal_arsine_complexes
lightly studied and fragile. At the other extreme, tris(dimethylamino)phosphine (P(NMe2)3) is commonly available. Intermediate members are known, such
Aminophosphine
Chemical compound
radical that plays a role in the chemiluminescence of phosphorus and phosphine. It is produced when phosphates are heated to high temperatures. In the
Phosphorus_dioxide
Chemical group (–CH3) derived from methane
Phosphodiester Phosphonate Phosphite Phosphonous Phosphinate Phosphine oxide Phosphine Phosphonium Phosphaalkene Phosphaalkyne Phosphaallene Arsenic
Methyl_group
Phosphiranes are organic compounds with the phosphirane functional group – a three-membered ring with two atoms of carbon and one atom of phosphorus that
Phosphiranes
Chemical compound
Tris(o-tolyl)phosphine is an organophosphorus compound with the formula P(C6H4CH3)3. It is a white, water-insoluble solid that is soluble in organic solvents
Tris(o-tolyl)phosphine
Phosphorus-containing ligands
Dialkylbiaryl phosphine ligands are phosphine ligands that are used in homogeneous catalysis. They have proved useful in Buchwald-Hartwig amination and
Dialkylbiaryl phosphine ligands
Dialkylbiaryl_phosphine_ligands
Chemical compound
Tris(hydroxymethyl)phosphine is the organophosphorus compound with the formula P(CH2OH)3. It is a white solid. The compound is multifunctional, consisting
Tris(hydroxymethyl)phosphine
Chemical reaction
Staudinger reaction is a chemical reaction of an organic azide with a phosphine or phosphite produces an iminophosphorane. The reaction was discovered
Staudinger_reaction
Chemical compound
temperature with irradiation: Sulfonation of PPh3 gives tris(3-sulfophenyl)phosphine, P(C6H4-3-SO3−)3 (TPPTS), usually isolated as the trisodium salt. In contrast
Triphenylphosphine
Atmospheric ghost lights
such as bioluminescence or chemiluminescence, caused by the oxidation of phosphine (PH 3), diphosphane (P 2H 4) and methane (CH 4), produced by organic decay
Will-o'-the-wisp
Concept in organic chemistry
coordinated to different metal centers. Tolman focused specifically on phosphine ligands, first cataloguing their general reactivity and then in 1970 measuring
Tolman_electronic_parameter
state III. Most phosphinous acids rapidly convert to the corresponding phosphine oxide, which is tetrahedral and is assigned oxidation state V. Only one
Phosphinous_acids
Astrochemist
for Astrophysics | Harvard & Smithsonian. Sousa-Silva is an expert on phosphine. She has contributed to investigations of the possibility of life on Venus
Clara_Sousa-Silva
Chemical compound
Aluminium phosphide reacts vigorously with water or acids to release phosphine. The phosphine is the basis of the toxicity of AlP. AlP is synthesized by combination
Aluminium_phosphide
Chemical compound
Tris(2,4,6-trimethoxyphenyl)phosphine (TTMPP) is a large triaryl organophosphine whose strong Lewis-basic properties make it useful as an organocatalyst
Tris(2,4,6-trimethoxyphenyl)phosphine
Tris(2,4,6-trimethoxyphenyl)phosphine
Chemical compound
P-Chiral phosphines are organophosphorus compounds of the formula PRR′R″, where R, R′, R″ = H, alkyl, aryl, etc. They are a subset of chiral phosphines, a broader
P-Chiral_phosphine
Geometric aspects of ions and molecules affecting their shape and reactivity
a widely used stabilizer in polymers. Tricyclohexylphosphine, a bulky phosphine ligand used in homogeneous catalysis and, with B(C6F5)3, comprises the
Steric_effects
Palladium-catalysed substitution reaction
1965 and, later, adapted by Barry Trost in 1973 with the introduction of phosphine ligands. The scope of this reaction has been expanded to many different
Tsuji–Trost_reaction
Chemical element with atomic number 15 (P)
phosphide (Ca3P2). Unlike ammonia, phosphine is oxidised by air. Phosphine is also far less basic than ammonia. Other phosphines are known which contain chains
Phosphorus
Form of interaction between two atoms
oxidation states that have ligands such as carbon monoxide, olefins, or phosphines. The ligands involved in π backbonding can be broken into three groups:
Pi_backbonding
Chemical compound
the disecondary phosphine: (C6H5)2PCH2CH2P(C6H5)2 4 Li → Li(C6H5)PCH2CH2P(C6H5)Li + 2 C6H5Li Hydrolysis gives the bis(secondary phosphine). Li(C6H5)PCH2CH2P(C6H5)Li
1,2-Bis(diphenylphosphino)ethane
1,2-Bis(diphenylphosphino)ethane
Organic compounds of the form >C=N–OH
Phosphodiester Phosphonate Phosphite Phosphonous Phosphinate Phosphine oxide Phosphine Phosphonium Phosphaalkene Phosphaalkyne Phosphaallene Arsenic
Oxime
Measure of the steric bulk of a ligand in a coordination complex
of the ligand atoms at the perimeter of the base of the cone. Tertiary phosphine ligands are commonly classified using this parameter, but the method can
Ligand_cone_angle
Chemical compound
of trimethylphosphine has predominantly s-character as is the case for phosphine, PH3. PMe3 can be prepared by the treatment of triphenyl phosphite with
Trimethylphosphine
Cyclic chemical group (–C6H5)
Phosphodiester Phosphonate Phosphite Phosphonous Phosphinate Phosphine oxide Phosphine Phosphonium Phosphaalkene Phosphaalkyne Phosphaallene Arsenic
Phenyl_group
66-telescope radio observatory in Chile
detection of phosphine, a biomarker, in the air of Venus. As no known non-biological source of phosphine on Venus could produce phosphine in the concentrations
Atacama Large Millimeter Array
Atacama_Large_Millimeter_Array
Organic compound
Phosphodiester Phosphonate Phosphite Phosphonous Phosphinate Phosphine oxide Phosphine Phosphonium Phosphaalkene Phosphaalkyne Phosphaallene Arsenic
Urea
Chemical compound
in the synthesis of various phosphines. A typical route uses Grignard reagents: Ph2PCl + MgRX → Ph2PR + MgClX The phosphines produced from reactions with
Chlorodiphenylphosphine
Chemical compound
formula P(CH2CH2CH2CH3)3, often abbreviated as PBu3. It is a tertiary phosphine. It is an oily liquid at room temperature, with a nauseating odor. It
Tributylphosphine
Chemical compound
reagent. Further treatment of Ph3PAuMe with methyllithium displaces the phosphine ligand and generates lithium dimethylaurate. Pierre Braunstein; Hans Lehner;
Chloro(triphenylphosphine)gold(I)
Chloro(triphenylphosphine)gold(I)
Class of main-group heterocycle
azaborine containing phosphines and traditional phosphine ligands. Their investigation found that 1,2-azaborine containing phosphine pictured in Figure
Azaborine
Psychoactive substance found in plants in the family Apocynaceae
2-(2-iodo-1H-indol-3-yl)ethanol. This is treated with iodine, triphenyl phosphine, and imidazole to form 2-iodo-3-(2-iodoethyl)-1H-indole. Then, using
Ibogaine
Radicals centered on boron atoms
the boron center. Phosphine-boryl radicals and dialkyl sulfide-boryl radicals were found to be distinct in their reactivities. Phosphine-boryl radicals were
Boryl_radicals
Chemical group (–C3H7) derived from propane
Phosphodiester Phosphonate Phosphite Phosphonous Phosphinate Phosphine oxide Phosphine Phosphonium Phosphaalkene Phosphaalkyne Phosphaallene Arsenic
Propyl_group
Organosulfur compounds containing –S(=O)2–N< functional group
Phosphodiester Phosphonate Phosphite Phosphonous Phosphinate Phosphine oxide Phosphine Phosphonium Phosphaalkene Phosphaalkyne Phosphaallene Arsenic
Sulfonamide
multiple bonds, but the reaction is probably most useful in reactions of phosphine with formaldehyde, a form of hydroxymethylation. Like other hydrofunctionalizations
Hydrophosphination
Functional group (C=O)
Phosphodiester Phosphonate Phosphite Phosphonous Phosphinate Phosphine oxide Phosphine Phosphonium Phosphaalkene Phosphaalkyne Phosphaallene Arsenic
Carbonyl_group
Organic molecule containing a neutral carbon with two unbound valence electrons
carbenes are usually very strong σ-donor spectator ligands, similar to phosphines. A large-scale application of carbenes is the industrial production of
Carbene
Type of poisoning
The toxicity of aluminium phosphide is attributed to the liberation of phosphine gas, a cytotoxic compound that causes free radical mediated injury, inhibits
Aluminium_phosphide_poisoning
Chemical compounds and groups containing nitrogen with a lone pair (:N)
Phosphodiester Phosphonate Phosphite Phosphonous Phosphinate Phosphine oxide Phosphine Phosphonium Phosphaalkene Phosphaalkyne Phosphaallene Arsenic
Amine
Chemical compound
P(C6H4SO3Na)3. This white solid is an unusual example of a water-soluble phosphine. Its complexes are also water-soluble. Its complex with rhodium is used
TPPTS
Chemical group made of an –S(=O)2 group bound to a halogen
Phosphodiester Phosphonate Phosphite Phosphonous Phosphinate Phosphine oxide Phosphine Phosphonium Phosphaalkene Phosphaalkyne Phosphaallene Arsenic
Sulfonyl_halide
Chemical compound
chelates metals via the two phosphine groups. Its name is derived from its description — being both chiral and a phosphine. As a C2-symmetric ligand, chiraphos
Chiraphos
Organic compounds made of alkyl/aryl groups bound to oxygen (R–O–R')
Phosphodiester Phosphonate Phosphite Phosphonous Phosphinate Phosphine oxide Phosphine Phosphonium Phosphaalkene Phosphaalkyne Phosphaallene Arsenic
Ether
Family of polyatomic cations containing phosphorus
protonation of primary, secondary, and tertiary phosphines: PR3 + H+ → HPR+ 3 The basicity of phosphines follows the usual trends, with R = alkyl being
Phosphonium
Chemical compound
In basic media, white phosphorus spontaneously disproportionates to phosphine and various phosphorus oxyacid salts. Many reactions of white phosphorus
White_phosphorus
Planned 2020s private Venus astrobiology probe
than summer 2026. Research published in 2020 indicated the presence of phosphine (PH3) in Venus's atmosphere, resulting in a widespread public and academic
Venus_Life_Finder
Chemical structure from which derivatives can be visualized
inorganic chemistry. Phosphines Phosphine is the parent of phosphines. Phenylphosphine is a derivative of the parent phosphine. 3,3′
Parent_structure
Organic compound containing a –C(=O)OH group
Phosphodiester Phosphonate Phosphite Phosphonous Phosphinate Phosphine oxide Phosphine Phosphonium Phosphaalkene Phosphaalkyne Phosphaallene Arsenic
Carboxylic_acid
Fluxional process in trigonal-pyramidal molecules
inversion applies to many types of molecules, including carbanions, amines, phosphines, arsines, stibines, and sulfoxides. The identity of the inverting atom
Pyramidal_inversion
Cast of neo-Western crime media franchise
explosion and flees, trapping Emilio and Krazy-8 inside the RV with deadly phosphine gas. Emilio dies and Jesse subsequently disposes of his body by dissolving
List of characters in the Breaking Bad franchise
List_of_characters_in_the_Breaking_Bad_franchise
Substance providing scientific evidence of past or present life
dioxide (CO2) by sunlight, is now offered an explanation for its presence. Phosphine (PH 3) was first detected in 2020 by the James Clerk Maxwell Telescope
Biosignature
Organic compounds of the form >C=O
Phosphodiester Phosphonate Phosphite Phosphonous Phosphinate Phosphine oxide Phosphine Phosphonium Phosphaalkene Phosphaalkyne Phosphaallene Arsenic
Ketone
Fifth planet from the Sun
carbon, oxygen, sulfur, neon, and compounds such as ammonia, water vapour, phosphine, hydrogen sulfide, and hydrocarbons. Jupiter's helium abundance is 80%
Jupiter
bisphosphanes, are organophosphorus compounds most commonly used as bidentate phosphine ligands in inorganic and organometallic chemistry. They are identified
Diphosphine_ligands
Cross-coupling reaction used in organic synthesis
strongly upon reaction conditions. With simple phosphines, such as PPh3 (n=2), and in case of bulky phosphines (i.e., P(o-Tol) 3) it was demonstrated that
Sonogashira_coupling
Chemical compound
seen through hydrogen/deuterium exchange, involved in the insertion of phosphines, and capable of forming post transition metal ethyl adducts. Barefield
Tantalocene_trihydride
Chemical group (–C(=O)C6H5
Phosphodiester Phosphonate Phosphite Phosphonous Phosphinate Phosphine oxide Phosphine Phosphonium Phosphaalkene Phosphaalkyne Phosphaallene Arsenic
Benzoyl_group
Chemical compound
phosphonium cation (PH+4). Phosphonium iodide is commonly used as storage for phosphine and as a reagent for substituting phosphorus into organic molecules. Phosphonium
Phosphonium_iodide
commercial chemicals are prepared through the cyanethylation of amines, phosphines, and carbon nucleophiles. For example, acetone is cyanoethylated to give
Cyanoethylation
Chemical compound
configuration at the phosphine. For example, cyclic chiral tertiary phosphine oxides can be reduced to cyclic tertiary phosphines. Phenylsilane combines
Phenylsilane
Overview of volcanic activity on the planet Venus
Historic data from Pioneer Venus also shows the possible detection of phosphine. Phosphine (PH3) is derived from phosphide (P3−) through the following interaction
Volcanism_on_Venus
Chemical group (–CH2–CH3)
Phosphodiester Phosphonate Phosphite Phosphonous Phosphinate Phosphine oxide Phosphine Phosphonium Phosphaalkene Phosphaalkyne Phosphaallene Arsenic
Ethyl_group
Term in organic chemistry
the loss of the single proton bonded to the middle nitrogen. Secondary phosphines have two 'R' groups attached to a phosphorus atom and again, a P-H bond
Secondary_(chemistry)
Triple star system in the constellation Cygnus
detected phosphine in the atmosphere of this brown dwarf, which was detected in a James Webb Space Telescope spectrum. The researchers find a phosphine abundance
Wolf_1130
Organic compound or functional group containing a C=N bond
doi:10.15227/orgsyn.065.0140. Ian P. Andrews and Ohyun Kwon (2011). "PHOSPHINE-CATALYZED [3 + 2] ANNULATION: SYNTHESIS OF ETHYL 5-(tert-BUTYL)-2-PHE
Imine
Any organic compound having a sulfanyl group (–SH)
Phosphodiester Phosphonate Phosphite Phosphonous Phosphinate Phosphine oxide Phosphine Phosphonium Phosphaalkene Phosphaalkyne Phosphaallene Arsenic
Thiol
Hydrocarbon compound (H2C=CH2)
Phosphodiester Phosphonate Phosphite Phosphonous Phosphinate Phosphine oxide Phosphine Phosphonium Phosphaalkene Phosphaalkyne Phosphaallene Arsenic
Ethylene
Chemical group (–OH)
Phosphodiester Phosphonate Phosphite Phosphonous Phosphinate Phosphine oxide Phosphine Phosphonium Phosphaalkene Phosphaalkyne Phosphaallene Arsenic
Hydroxy_group
Chemical compound
CPhos is a phosphine ligand derived from biphenyl. It is a white solid that is soluble in organic solvents. Its palladium complexes exhibit high activity
CPhos
Chemical compound
"Trans-Tricarbonylbis(Phosphine)Iron(0) Complexes: One-Pot Syntheses from Pentacarbonyliron". trans-Tricarbonylbis(Phosphine)Iron(0) Complexes: One-Pot
Potassium tetracarbonyliron hydride
Potassium_tetracarbonyliron_hydride
Ghost light reported in the Banni grasslands, Kutch district, Gujarat State, India
of phosphine (PH3), diphosphane (P2H4), and methane (CH4). These compounds, produced by organic decay, can cause photon emissions. Since phosphine and
Chir_batti
British organic chemist and professor at Bristol
Cambridge working with Dr Stuart Warren on asymmetric synthesis using phosphine oxide chemistry. He then carried out a postdoc with Prof Marc Julia and
Jonathan_Clayden
Configuration of atoms within a molecule
Phosphine, an example of a molecule with a trigonal pyramidal geometry.
Trigonal pyramidal molecular geometry
Trigonal_pyramidal_molecular_geometry
Compound derived from an acid
Phosphodiester Phosphonate Phosphite Phosphonous Phosphinate Phosphine oxide Phosphine Phosphonium Phosphaalkene Phosphaalkyne Phosphaallene Arsenic
Ester
Class of chemical compounds
Phosphodiester Phosphonate Phosphite Phosphonous Phosphinate Phosphine oxide Phosphine Phosphonium Phosphaalkene Phosphaalkyne Phosphaallene Arsenic
Sulfite_ester
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