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PubMed · 11796050

Toward a stable hydroxyphosphorane.

Robert E Hanes·Vincent M Lynch·Eric V Anslyn·Kevin N Dalby
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Abstract

[reaction: see text] Hydroxy-pentaoxy-phosphoranes are transient intermediates formed during the hydrolysis of various phosphoesters. Kinetic analyses support the existence of such compounds, although they are not isolated. In an attempt to create a stable example, 2 equiv of a ligand possessing a very high effective molarity were attached to a central phosphorus. Instead of obtaining a hydroxyphosphorane, analysis by (31)P and (19)F NMR spectroscopy and X-ray crystallography showed the product to be a phosphotriester. The reason for this is discussed.

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Crystallography, X-RayDNADrug StabilityHydrolysisLigandsMagnetic Resonance SpectroscopyMolecular StructureOrganophosphatesPhosphoranesRNAJournal ArticleResearch Support, Non-U.S. Gov'tResearch Support, U.S. Gov't, Non-P.H.S.

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Robert E Hanes, Vincent M Lynch, Eric V Anslyn, Kevin N Dalby. 2002-01-24. Toward a stable hydroxyphosphorane.. https://doi.org/10.1021/ol016941d

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