P,P'-(di-n-octyl) dihydrogen pyrophosphonic acid | 72492-60-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: P,P'-(di-n-octyl) dihydrogen pyrophosphonic acid
• 英文别名: [Hydroxy(octyl)phosphoryl]oxy-octylphosphinic acid
• CAS: 72492-60-5
• 化学式: C₁₆H₃₆O₅P₂
• 分子量: 370.406
• InChiKey: HTBLRRWSRWPFDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  辛基膦酸 在 N,N'-二环己基碳二亚胺 作用下， 以 乙醚 为溶剂， 反应 0.42h， 以57%的产率得到P,P'-(di-n-octyl) dihydrogen pyrophosphonic acid
  参考文献：
  名称：

  Identification of Acidic Phosphorus-Containing Ligands Involved in the Surface Chemistry of CdSe Nanoparticles Prepared in Tri-N-octylphosphine Oxide Solvents

  摘要：

  The surface ligand composition of CdSe nanoparticles prepared using technical grade tri-n-octylphosphine oxide (TOPO) was investigated using a nucleophilic ligand displacement methodology and 31 p {H-1} NMR spectroscopy. 4-(N,N-Dimethylamino)pyridine (DMAP) and benzyltrimethylammonium propionate were added to tetrahydrofuran solutions of CdSe nanoparticles prepared in technical grade TOPO. DMAP was shown to be a sufficiently strong nucleophile to displace the more weakly coordinating ligands, TOPO, TOPSe, di-n-octylphosphinate, and n-octylphosphonate (OPA). Benzyltrimethylammonium propionate was shown to be a stronger nucleophile than DMAP in that it could displace all the aforementioned surface-bound ligands as well as a previously unidentified surface-bound phosphorus species. Independent synthesis and P-31 {H-1} NMR spectral matching confirmed that the new species was P,P'-(di-n-octyl) dihydrogen pyrophosphonic acid (PPA). The PPA was shown to form during the nanoparticle synthesis via the dehydrative condensation of OPA. CdSe nanoparticle syntheses were performed using pure TOPO and added OPA, and subsequent displacement experiments showed that OPA and PPA were the predominant surface-bound ligands. CdSe nanoparticle syntheses were performed using pure TOPO and added PPA, and subsequent displacement experiments showed that PPA was the predominant surface-bound ligand. PPA was also shown to have the greatest affinity for the nanoparticle surface of all the ligands investigated. Thus, a model for the surface ligand composition could be developed for nanoparticles prepared using technical grade TOPO or other high-boiling solvents with added acidic phosphorus compounds.

  DOI：

  10.1021/ja077414d

文献信息

• US5756638A
  申请人：——

  公开号：US5756638A

  公开（公告）日：1998-05-26