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In biochemistry and medicinal chemistry, phosphonate groups are used as stable bioisosteres for phosphate, such as in the antiviral nucleotide analog, Tenofovir, one of the cornerstones of anti-HIV therapy. And there is an indication that phosphonate derivatives are "promising ligands for nuclear medicine." [2]
Although they are derivatives of phosphonous acid (RP(OH) 2), [2] they are not prepared from such precursors. Phosphonites are prepared by alcoholysis of organophosphinous chlorides. For example, treatment of dichlorophenylphosphine with methanol and base gives dimethyl phenylphosphonite: Cl 2 PPh + 2 CH 3 OH → (CH 3 O) 2 PPh + 2 HCl
They exhibit tautomerism, however, the equilibrium overwhelmingly favours the right-hand (phosphonate-like) form: [11] [12] (RO) 2 POH ⇌ (RO) 2 P(O)H The P-H bond is the site of high reactivity in these compounds (for example in the Atherton–Todd reaction and Hirao coupling ), whereas in tri-organophosphites the lone pair on phosphorus is ...
Aminophosphonates are often prepared by hydrophosphonylation, usually the condensation of imines and phosphorous acid.In the Pudovik reaction or Kabachnik–Fields reaction, the esters of phosphorous acid are employed, e.g. diphenylphosphite.
A typical derivative is the salt [NH 4][HP(O) 2 OH]. [7] [6] Many related salts are known, e.g., RbHPHO 3, CsHPHO 3, TlHPHO 3. These salts are prepared by treating phosphorous acid with the metal carbonate. These compounds contain a layer polymeric anion consisting of HPO 3 tetrahedra linked by hydrogen bonds. These layers are interleaved by ...
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[4] [5] Despite being named as a phosphite the compound exists overwhelmingly in its phosphonate form, (C 2 H 5 O) 2 P(O)H, a property it shares with its parent acid phosphorous acid. Nonetheless many of its reactions appear to proceed via the minor phosphorus(III) tautomer. [6] (C 2 H 5 O) 2 P III (OH) ⇌ (C 2 H 5 O) 2 P V (O)H, K = 15 x 10 6 ...
Dimethylphosphite, is a minor tautomer of the phosphorus(V) derivative. It is a reagent for generating other organophosphorus compounds, exploiting the high reactivity of the P-H bond. The molecule is tetrahedral. It is a colorless liquid.