title: Toward a stable hydroxyphosphorane.
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.
authors.affiliation: The Department of Chemistry, Division of Medicinal Chemistry, The University of Texas at Austin, Austin, Texas 78712, USA.
authors.forename: Robert E
authors.initials: RE
authors.lastname: Hanes
authors.forename: Vincent M
authors.initials: VM
authors.lastname: Lynch
authors.forename: Eric V
authors.initials: EV
authors.lastname: Anslyn
authors.forename: Kevin N
authors.initials: KN
authors.lastname: Dalby
mesh_terms: D018360:Crystallography, X-Ray; D004247:DNA / Q000378:metabolism; D004355:Drug Stability; D006868:Hydrolysis; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010755:Organophosphates / Q000378:metabolism; D010753:Phosphoranes / Q000737:chemistry*; D012313:RNA / Q000378:metabolism
chemical_list: D008024:Ligands; D010755:Organophosphates; D010753:Phosphoranes; D012313:RNA; D004247:DNA