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Phosphine sulfide

From Wikipedia, the free encyclopedia

A phosphine sulfide is an organophosphorus compound with the formula R3PS. They are typically colorless, air-stable solids. A common example of a tertiary phosphine sulfide is triphenylphosphine sulfide. Phosphine sulfides are sometimes intermediates in the synthesis of tertiary phosphines. Phosphine sulfides are tetrahedral.

Synthesis

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Phosphine sulfides are usually prepared by the oxidation of tertiary phosphines with elemental sulfur. The heat of formation of phosphine sulfides from tertiary phosphines and elemental sulfur scale with the basicity of the phosphine.[1]

Enthalpy for sulfiding various tertiary phosphines
Tertiary phosphine ∆H (kcal/mol) for reaction with S8 Tertiary phosphine sulfide CAS No
PCy3 -30.9 ± 1.9 S=PCy3 42201-98-9
PBu3 -28.9 ± 0.3 S=PBu3 3084-50-2
PMe3 -27.1 ± 0.4 S=PMe3 2404-55-9
PMe2Ph -26.0 ±0.5 S=PMe2Ph 1707-00-2
PMePh2 -23.8 ±0.3 S=PMePh2 13639-74-2
PPh3 -21.5 ±0.3 S=PPh3 3878-45-3

References

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  1. ^ Capps, Kenneth B.; Wixmerten, Bodo; Bauer, Andreas; Hoff, Carl D. (1998). "Thermochemistry of Sulfur Atom Transfer. Enthalpies of Reaction of Phosphines with Sulfur, Selenium, and Tellurium, and of Desulfurization of Triphenylarsenic Sulfide, Triphenylantimony Sulfide, and Benzyl Trisulfide". Inorganic Chemistry. 37 (12): 2861–2864. doi:10.1021/ic9715862.