Nucleophilic substitution reactions between diphosphonate and orthophosphate characterized by high-performance liquid chromatography and 31P NMR spectroscopy.
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概要
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Inorganic diphosphonate with phosphorus of an oxidation number +3 was found to react with orthophosphate (oxidation number +5) at 50 °C to give phosphonylated compounds; dimeric isohypophosphate (oxidation numbers +3 and +5) and a novel trimeric compound (oxidation numbers +3 and +5). Orthophosphate ion is considered to act as a ligand with two or three nucleophilic sites that were phosphonylated stepwise by diphosphonate. Kinetic processes of the nucleophilic reactions were monitored by HPLC and <SUP>31</SUP>P NMR. Two products, the dimer having one P–H bond and the trimer with two P–H bonds, were well-resolved by HPLC and their yields, based on orthophosphate applied, were 85% (dimer) and 3% (trimer) when a mixed solution of 0.5 M diphosphonate and 0.1 M orthophosphate was incubated at 50 °C for 21 h. A complicated <SUP>31</SUP>P NMR spectrum that indicated a large coupling constant(<I>J</I><SUB>PH</SUB>=650 Hz) and grew with incubation time is reasonably assigned to the unsymmetrical isohypophosphate composed of both a phosphate group and a phosphonate group. Apparent formation constants of the dimer and trimer were evaluated.
- 公益社団法人 日本化学会の論文
著者
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Yoza Norimasa
Department Of Chemistry Faculty Of Science Kyushu University
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MIYAJIMA Tohru
Department of Chemistry and Applied Chemistry, Faculty of Science and Engineering, Saga University
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MIYAJIMA Tohru
Department of Chemistry, Faculty of Science, Kyushu University
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Tokushige Noriko
Department of Chemistry, Faculty of Science, Kyushu University
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Okamatsu Miki
Department of Chemistry, Faculty of Science, Kyushu University
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Baba Yoshinobu
Kobe Women's College of Pharmacy
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