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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, organyl or halogen group). These cations have tetrahedral structures.
According to X-ray crystallography, [(i-Pr 2 N) 2 P] + is nearly planar consistent with sp 2-hybridized phosphorus center. [6] The planarity of the nitrogen center is consistent with the resonance of the lone pair of the nitrogen atom as a pi bond to the empty phosphorus 3p orbital perpendicular to the N−P−N plane.
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 .
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Tetraphenylphosphonium chloride is the chemical compound with the formula [(C 6 H 5) 4 P]Cl, abbreviated Ph 4 PCl or PPh 4 Cl or [PPh 4]Cl, where Ph stands for phenyl. Tetraphenylphosphonium and especially tetraphenylarsonium salts were formerly of interest in gravimetric analysis of perchlorate and related oxyanions.
Most processes begin with phosphorous acid (aka phosphonic acid, H 3 PO 3), exploiting its reactive P−H bond. [1] [3]Phosphonic acid can be alkylated via the Kabachnik–Fields reaction or Pudovik reaction to give aminophosphonate, which are useful as chelating agents.
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Tetrakis(hydroxymethyl)phosphonium chloride (THPC) is an organophosphorus compound with the chemical formula [P(CH 2 OH) 4]Cl. It is a white water-soluble salt with applications as a precursor to fire-retardant materials [ 1 ] and as a microbiocide in commercial and industrial water systems.