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Phosphonium information


Phosphonium ion
Structure of PH+
4
, the parent phosphonium cation.

In chemistry, the term phosphonium (more obscurely: phosphinium) describes polyatomic cations with the chemical formula PR+
4
(where R is a hydrogen or an alkyl, aryl, or halide group). These cations have tetrahedral structures. The salts are generally colorless or take the color of the anions.[1]

  1. ^ Corbridge, D. E. C. (1995). Phosphorus: An Outline of its Chemistry, Biochemistry, and Technology (5th ed.). Amsterdam: Elsevier. ISBN 978-0-444-89307-9.

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Phosphonium

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In chemistry, the term phosphonium (more obscurely: phosphinium) describes polyatomic cations with the chemical formula PR+ 4 (where R is a hydrogen or...

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Phosphonium iodide

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Phosphonium iodide is a chemical compound with the formula PH 4I. It is an example of a salt containing an unsubstituted phosphonium cation (PH+ 4). Phosphonium...

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Phosphonium coupling

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In organic chemistry, phosphonium coupling is a cross-coupling reaction for organic synthesis. It is a mild, efficient, chemoselective and versatile methodology...

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Wittig reaction

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olefination is a chemical reaction of an aldehyde or ketone with a triphenyl phosphonium ylide called a Wittig reagent. Wittig reactions are most commonly used...

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Ylide

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Consequently, the carbon anion is trigonal pyramidal.[citation needed] Phosphonium ylides are used in the Wittig reaction, a method used to convert ketones...

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Organophosphorus chemistry

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organophosphorus compounds. Compounds with the formula [PR4+]X− comprise the phosphonium salts. These species are tetrahedral phosphorus(V) compounds. From the...

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Wittig reagents

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to be sold commercially. Wittig reagents are usually prepared from a phosphonium salt, which is in turn prepared by the quaternization of triphenylphosphine...

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Betaine

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group that bears no hydrogen atom, such as a quaternary ammonium or phosphonium cation (generally: onium ions), and with a negatively charged functional...

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Peptide synthesis

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completely and incorporate the HOAt/HOBt moiety as an aminium/uronium or phosphonium salt of a non-nucleophilic anion (tetrafluoroborate or hexafluorophosphate)...

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Counterion

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Bis(triphenylphosphine)iminium chloride is the chloride salt of a bulky lipophilic phosphonium cation [Ph3PNPPh3]+. Tetraphenylphosphonium chloride (C6H5)4PCl, abbreviated...

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Ionic liquid

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the acid and base. Phosphonium cations (R4P+) are less common but offer some advantageous properties. Some examples of phosphonium cations are...

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HBTU

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by analogy with the corresponding phosphonium salts, which bear a positive carbon atom instead of the phosphonium residue. Later, it was shown by X-ray...

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Triphenylphosphine

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triphenylphosphine dichloride ([PPh3Cl]Cl), which exists as the moisture-sensitive phosphonium halide. This reagent is used to convert alcohols to alkyl chlorides in...

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Georg Wittig

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synthesis of alkenes from aldehydes and ketones using compounds called phosphonium ylides in the Wittig reaction. He shared the Nobel Prize in Chemistry...

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Benzene

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Phosphonate Phosphite Phosphonous Phosphinate Phosphine oxide Phosphine Phosphonium Phosphaalkene Phosphaalkyne Phosphaallene Sulfur Thiol Sulfide Sulfonium...

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Cyclohexane

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Kohlenwasserstoffe durch Jodphosphonium" [On the reduction of aromatic compound by phosphonium iodide [H4IP]]. Annalen der Chemie und Pharmacie. 55: 266–281. Bei der...

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Carboxylic acid

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Phosphonate Phosphite Phosphonous Phosphinate Phosphine oxide Phosphine Phosphonium Phosphaalkene Phosphaalkyne Phosphaallene Sulfur Thiol Sulfide Sulfonium...

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Dimethyl sulfoxide

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base, e.g., for the deprotonation of ketones to form sodium enolates, phosphonium salts to form Wittig reagents, and formamidinium salts to form diaminocarbenes...

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Oxime

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Phosphonate Phosphite Phosphonous Phosphinate Phosphine oxide Phosphine Phosphonium Phosphaalkene Phosphaalkyne Phosphaallene Sulfur Thiol Sulfide Sulfonium...

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Methyltriphenylphosphonium bromide

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compound with the formula [(C6H5)3PCH3]Br. It is the bromide salt of a phosphonium cation. It is a white salt that is soluble in polar organic solvents...

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Zwitterion

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located on a quaternary ammonium group. Similarly, a molecule containing a phosphonium group and a carboxylate group cannot isomerize. Tautomerism of amino...

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Phosphine

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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...

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Ketone

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reaction with an electrophile gives a resonance stabilized cation With phosphonium ylides in the Wittig reaction to give the alkenes With thiols to give...

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Ether

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Phosphonate Phosphite Phosphonous Phosphinate Phosphine oxide Phosphine Phosphonium Phosphaalkene Phosphaalkyne Phosphaallene Sulfur Thiol Sulfide Sulfonium...

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