phenylphosphonic acid mono(3-hydroxynaphthalen-2-yl)ester | 794-91-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: phenylphosphonic acid mono(3-hydroxynaphthalen-2-yl)ester
• 英文别名: <3-Hydroxy-naphthyl-2>-hydrogenphenylphosphonat；(3-Hydroxy-naphthyl-2)-hydrogenphenylphosphonat
• CAS: 794-91-2
• 化学式: C₁₆H₁₃O₄P
• 分子量: 300.251
• InChiKey: QXIYSAIADDXXKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.76
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  苯膦酰二氯 、 2,3-二羟基萘 生成 phenylphosphonic acid mono(3-hydroxynaphthalen-2-yl)ester
  参考文献：
  名称：

  A study of the condenstaion of arenediols with phenylphosphonic dichloride

  摘要：

  DOI：

  10.1016/s0040-4020(01)90852-x

文献信息

• The structures of phenylphosphonic-acid-mono-(2-hydroxy-phenyl)ester and phenylphosphonic-acid-mono-(3-hydroxy-naphthalen-2-yl)ester – A combined experimental and theoretical study
  作者：Richard Betz

  DOI：10.1016/j.poly.2014.11.017

  日期：2015.2

  Two ester derivatives of phenylphosphonic acid were prepared from vicinal aromatic diols and phenylphosphonic dichloride in one-step procedures. The products were characterized by means of multi-nuclear NMR spectroscopy (H-1, C-13, P-31) mass spectrometry, elemental analysis. UV-Vis spectroscopy, and melting point as well as vibrational spectroscopy. Their molecular structures were determined by single crystal X-ray diffraction and found to be open-chain half-esters of the respective diols. Intermolecular contacts and hydrogen bonding were analyzed. Born-Haber-cycles based on DFT calculations were conducted for the partial hydrolysis of the assumed cyclic phenylphosphonates to assess the reaction energies for the partial P-O-C cleavage of the chelate rings. The observed partial hydrolysis was rationalized on grounds of molecular orbital considerations. Experimental data were correlated to DFT data. The bonding situation of the two compounds was described by means of NBO analyses. (C) 2014 Elsevier Ltd. All rights reserved.