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Phosphine (IUPAC name: phosphane) 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 ).
The latter is a common feature of the chemistry of phosphorus. As a result, the lone pair of trimethylphosphine has predominantly s-character as is the case for phosphine, PH 3. [10] Tertiary phosphines are pyramidal. When the organic substituents all differ, the phosphine is chiral and
Phosphine (PH 3) and its organic derivatives (PR 3) are structural analogues of ammonia (NH 3), but the bond angles at phosphorus are closer to 90° for phosphine and its organic derivatives. Phosphine is an ill-smelling, toxic gas. Phosphorus has an oxidation number of −3 in phosphine. Phosphine is produced by hydrolysis of calcium phosphide ...
Phosphines or phosphanes are phosphorus compounds derived from phosphine and have the general structure R 3 P. For the nitrogen analogues, please see Category:Inorganic amines . Wikimedia Commons has media related to Phosphines .
Compounds related to phosphine oxides include phosphine imides (R 3 PNR') and related chalcogenides (R 3 PE, where E = S, Se, Te). These compounds are some of the most thermally stable organophosphorus compounds. In general, they are less basic than the corresponding phosphine oxides, which can adduce to thiophosphoryl halides: [7]: 73
Phosphonium iodide is a powerful substitution reagent in organic chemistry; for example, it can convert a pyrilium into a phosphinine via substitution. [3] In 1951, Glenn Halstead Brown found that PH 4 I reacts with acetyl chloride to produce an unknown phosphine derivative, possibly CH 3 C(=PH)PH 2 ·HI .
One of the first applications of phosphine ligands in catalysis was the use of triphenylphosphine in "Reppe" chemistry (1948), which included reactions of alkynes, carbon monoxide, and alcohols. [16] In his studies, Reppe discovered that this reaction more efficiently produced acrylic esters using NiBr 2 (PPh 3) 2 as a catalyst instead of NiBr 2.
The first phosphorine to be isolated is 2,4,6-triphenylphosphorine. It was synthesized by Gottfried Märkl in 1966 by condensation of the corresponding pyrylium salt and phosphine or its equivalent ( P(CH 2 OH) 3 and P(SiMe 3) 3). [3] The (unsubstituted) parent phosphorine was reported by Arthur J. Ashe III in 1971.