Toward a stable hydroxyphosphorane.
[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.
Hanes
Robert E
RE
The Department of Chemistry, Division of Medicinal Chemistry, The University of Texas at Austin, Austin, Texas 78712, USA.
Lynch
Vincent M
VM
Anslyn
Eric V
EV
Dalby
Kevin N
KN
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
D008024:Ligands; D010755:Organophosphates; D010753:Phosphoranes; D012313:RNA; D004247:DNA