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Phosphoryl chloride (commonly called phosphorus oxychloride) is a colourless liquid with the formula P O Cl 3. It hydrolyses in moist air releasing phosphoric acid and fumes of hydrogen chloride . It is manufactured industrially on a large scale from phosphorus trichloride and oxygen or phosphorus pentoxide . [ 4 ]
The nature of the P–O bond was once hotly debated. Some discussions invoked a role for phosphorus-centered d-orbitals in bonding, but this analysis is not supported by computational analyses. In terms of simple Lewis structure, the bond is more accurately represented as a dative bond, as is currently used to depict an amine oxide. [3] [4]
This page provides supplementary chemical data on phosphoryl chloride. Material Safety Data Sheets ... Structure and properties Index of refraction: 1.460 Dielectric ...
Thiophosphoryl fluoride reduces oxygenated compounds to give phosphoryl fluoride and sulfur: [9] [11] PSF 3 + SO 3 → POF 3 + SO 2 2 PSF 3 + SO 2 → 2 POF 3 + 3 S. The latter reaction also indicates why PSF 3 is not formed from PF 3 and SO 2. [9] Various oxidants can convert thiophosphoryl fluoride to phosphorus dichloride trifluoride, e.g.: [12]
This Lewis basicity is exploited in the Kinnear–Perren reaction to prepare alkylphosphonyl dichlorides (RP(O)Cl 2) and alkylphosphonate esters (RP(O)(OR') 2). Alkylation of phosphorus trichloride is effected in the presence of aluminium trichloride give the alkyltrichlorophosphonium salts, which are versatile intermediates: [16]
Thiophosphoryl chloride has tetrahedral molecular geometry and C 3v molecular symmetry, with the structure S=PCl 3.According to gas electron diffraction, the phosphorus–sulfur bond length is 189 pm and the phosphorus–chlorine bond length is 201 pm, while the Cl−P−Cl bond angle is 102°.
This trigonal bipyramidal structure persists in nonpolar solvents, such as CS 2 and CCl 4. [5] In the solid state PCl 5 is an ionic compound called tetrachlorophosphonium hexachlorophosphate formulated PCl + 4 PCl − 6. [6] Structure of solid phosphorus pentachloride, illustrating its autoionization at higher concentrations. [7]
Acetyl chloride was first prepared in 1852 by French chemist Charles Gerhardt by treating potassium acetate with phosphoryl chloride. [4]Acetyl chloride is produced in the laboratory by the reaction of acetic acid with chlorodehydrating agents such as phosphorus trichloride (PCl 3), phosphorus pentachloride (PCl 5), sulfuryl chloride (SO 2 Cl 2), phosgene, or thionyl chloride (SOCl 2).