N(9),N(9')-trimethylene-bishypoxanthine | 94891-04-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: N(9),N(9')-trimethylene-bishypoxanthine
• 英文别名: 1,3-bis(hypoxanthin-9-yl)propane；9-[3-(6-oxo-1H-purin-9-yl)propyl]-1H-purin-6-one
• CAS: 94891-04-0
• 化学式: C₁₃H₁₂N₈O₂
• 分子量: 312.291
• InChiKey: ZNPAHJRSRGMEHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N(9),N(9')-trimethylene-bishypoxanthine 、 zinc(II) chloride 以 盐酸 为溶剂， 生成 [(H-N(9),N(9')-trimethylene-bishypoxanthine)2(CH2)3][ZnCl4]*1.5H2O
  参考文献：
  名称：

  Anion−π Interactions in Bisadenine Derivatives:  A Combined Crystallographic and Theoretical Study

  摘要：

  In this manuscript we report a high-level ab initio study of anion-pi interactions involving N-9-methyl-adenine, N-6-methyl-adenine, N-9-methyl-hypoxanthine, a dimer of N-9-methyl-adenine, and N-9,N-9'-trimethylene-bisadenine. DNA bases like adenine are electron-deficient arenes that are well suited for interacting favorably with anions. We demonstrate that these compounds are able to interact favorably with anions. N-9-Methyl-adenine, N-6-methyl-adenine, and the dimer of M-methyl-adenine interact with the anion via the six-membered ring more strongly than adenine due to cooperativity effects between the noncovalent pi-pi and anion-pi interactions. This pattern, i.e., coexistence of pi-pi and anion-pi bonding, is observed experimentally in the solid state. Finally, we report the solid-state characterization of two new compounds N-6,N-6-dimethylene-bisadenine hydrochloride and an outer-sphere complex of protonated N-9,N-9-trimethylene-bishypoxanthine with zinc tetrachloride anion, that exhibit interesting anion-pi interactions. They are in strong agreement with high-level theoretical calculations.

  DOI：

  10.1021/ic701555n

文献信息

• Platinum antitumor agent coordination chemistry. Syntheses of linked purines and their platinum complexes. Crystal and molecular structures of bis[.mu.-1,4-bis(hypoxanthin-9-yl)butane]bis[(diaminoethane)(platinum(II)] tetrakis(hexafluorophosphate) hydrate
  作者：Barbara L. Hey、Kazuo Shinozuka、Sandra K. Miller、Donald G. VanDerveer、Luigi G. Marzilli

  DOI：10.1021/ic00199a006

  日期：1985.2
• Anion−π Interactions in Bisadenine Derivatives:  A Combined Crystallographic and Theoretical Study
  作者：Angel Garcia-Raso、Francisca M. Albertí、Juan J. Fiol、Andres Tasada、Miquel Barceló-Oliver、Elies Molins、Daniel Escudero、Antonio Frontera、David Quiñonero、Pere M. Deyà

  DOI：10.1021/ic701555n

  日期：2007.12.1

  In this manuscript we report a high-level ab initio study of anion-pi interactions involving N-9-methyl-adenine, N-6-methyl-adenine, N-9-methyl-hypoxanthine, a dimer of N-9-methyl-adenine, and N-9,N-9'-trimethylene-bisadenine. DNA bases like adenine are electron-deficient arenes that are well suited for interacting favorably with anions. We demonstrate that these compounds are able to interact favorably with anions. N-9-Methyl-adenine, N-6-methyl-adenine, and the dimer of M-methyl-adenine interact with the anion via the six-membered ring more strongly than adenine due to cooperativity effects between the noncovalent pi-pi and anion-pi interactions. This pattern, i.e., coexistence of pi-pi and anion-pi bonding, is observed experimentally in the solid state. Finally, we report the solid-state characterization of two new compounds N-6,N-6-dimethylene-bisadenine hydrochloride and an outer-sphere complex of protonated N-9,N-9-trimethylene-bishypoxanthine with zinc tetrachloride anion, that exhibit interesting anion-pi interactions. They are in strong agreement with high-level theoretical calculations.