phosphoranen.
/ˈfɒsfəreɪn/, U.S. /ˈfɑsfəˌreɪn/ Chemistry.† 1. Humphry Davy's name for: a supposed compound of one atom of phosphorus with one of chlorine. Obsolete.
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1812 H. Davy Elem. Chem. Philos. 292 I have already referred to the substance produced by passing phosphorus through corrosive sublimate... It may be called phosphorane.
1818 H. Davy in Philos. Trans. (Royal Soc.) 108 328 If the absorption of chlorine in forming phosphorane be made the datum.
2. A (hypothetical) hydride of pentavalent phosphorus, PH5; any of a series of (real) compounds regarded as substituted derivatives of this.
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the world > matter > chemistry > elements and compounds > metals > specific elements > phosphorus > [noun] > compounds > other
phosphonium1859
phosphine1870
phosphonitrile1921
phosphorane1952
tepa1953
phosphosilicate1964
1952 Chem. & Engin. News 2 June 2336/2 Ph5 is phosphorane (not phosphane, as the latter name is used in the series diphosphane, triphosphane, and so on..).
1963 Q. Rev. Chem. Soc. 17 411 Stable phosphoranes of the formula Ph3P:CXY (X, Y = CN, CO2R, COR) can be obtained.
1971 P. A. T. Hoye in Mellor's Comprehensive Treat. Inorg. & Theoret. Chem. VIII. Suppl. iii. xxxiii. 881 Pentaphenylphosphorane was first obtained by Wittig and Rieber by the reaction of tetraphenylphosphonium iodide with phenyl lithium... The phosphoranes (C6H5)4PC(C6H5)3 and p-CH3·C6H4P(C6H5)4 are prepared similarly.
1984 N. N. Greenwood & A. Earnshaw Chem. of Elements (1986) xii. 564 Phosphorane, PH5, has not been prepared or even detected, despite numerous attempts.
2004 Trends Biochem. Sci. 29 496 (caption) In the addition–elimination mechanism, bond making to form a pentavalent phosphorane intermediate precedes bond breaking.
This entry has been updated (OED Third Edition, March 2006; most recently modified version published online March 2022).
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