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tetraphenylphosphonium chloride : ウィキペディア英語版
tetraphenylphosphonium chloride

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Tetraphenylphosphonium chloride is the chemical compound with the formula (C6H5)4PCl, abbreviated Ph4PCl or PPh4Cl. Tetraphenylphosphonium and especially tetraphenylarsonium salts were formerly of interest in gravimetric analysis of perchlorate and related oxyanions. This colourless salt is used to generate lipophilic salts from inorganic and organometallic anions. Thus, Ph4P+ is useful as a phase-transfer catalyst, again because it allows inorganic anions to dissolve in organic solvents.
==Structure and basic properties==
The cation is tetrahedral. PPh4Cl crystallises as the anhydrous salt,〔J. F. Richardson, J. M. Ball, P. M. Boorman "Structure of Tetraphenylphosphonium Chloride" ''Acta Crystallographica'' 1986, volume C42, pp. 1271-1272. .〕 which is normal item of commerce, as well as a monohydrate〔E. E. Schweizer, C. J. Baldacchini, A. L. Rheingold "Tetraphenylphosphonium Chloride Monohydrate, Tetraphenylphosphonium Bromide and Tetraphenylphosphonium Iodide" ''Acta Crystallographica'' 1989. volume C45, page 1236-1239. .〕 and a dihydrate.〔A. J. Blake, C. D. Garner, J. M. Tunney "Tetraphenylphosphonium Chloride Dihydrate" ''Acta Crystallographica'' 2003, volume E59, o9-o10. 〕
In X-ray crystallography, PPh4+ salts are of interest as they often crystallise easily. The rigidity of the phenyl groups facilitates packing and elevates the melting point relative to alkyl-based quaternary ammonium salts. Also, since these salts are soluble in organic media, a wide range of solvents can be employed for their crystallisation.



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