EDTA bis-1-adamantanylamine

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: EDTA bis-1-adamantanylamine
• 英文别名: 2-[[2-(1-Adamantylamino)-2-oxoethyl]-[2-[[2-(1-adamantylamino)-2-oxoethyl]-(carboxymethyl)amino]ethyl]amino]acetic acid；2-[[2-(1-adamantylamino)-2-oxoethyl]-[2-[[2-(1-adamantylamino)-2-oxoethyl]-(carboxymethyl)amino]ethyl]amino]acetic acid
• 化学式: C₃₀H₄₆N₄O₆
• 分子量: 558.718
• InChiKey: MYYONJXHVZJOCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  139
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  乙二胺四乙酸二酐 、 金刚烷胺 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 EDTA bis-1-adamantanylamine
  参考文献：
  名称：

  Thermodynamics of Formation of Host−Guest Supramolecular Polymers

  摘要：

  The interactions between three beta-cyclodextrin hosts (having 1-3 binding sites) and two adamantyl guests (having 1-2 binding sites) have been studied by ITC, ROESY, static and dynamic light scattering (SLS and DLS), and AFM and TEM techniques. The enthalpy and free energy values (determined from ITC experiments) evidence that the single interaction between one binding site of the guest and one binding site of the host is independent of the number of binding sites of the interacting species. The average values are Delta H degrees = -26.6 +/- 2.3 kJ mol(-1) and Delta G degrees = -30.4 +/- 3.2 kJ mol(-1), indicating that the process is mainly enthalpy driven. In all cases, the experimental molar ratio (from ITC experiments) agrees with the expected one from the number of binding sites of both the host and guest. The formation of polymer-like entities was demonstrated by SLS, DLS, AFM, and TEM measurements. The structure of polymers is linear when both the host and the guest are ditopic entities and dendritic (or Cayley tree type) when the host and the guest have three and two binding sites, respectively.

  DOI：

  10.1021/ja0572809

文献信息

• Synthesis and characterization of a new photoinduced switchable β-cyclodextrin dimer
  作者：Florian Hamon、Claire Blaszkiewicz、Marie Buchotte、Estelle Banaszak-Léonard、Hervé Bricout、Sébastien Tilloy、Eric Monflier、Christine Cézard、Laurent Bouteiller、Christophe Len、Florence Djedaini-Pilard

  DOI：10.3762/bjoc.10.304

  日期：——

  This paper reports an efficient preparation of bridged bis-β-CD AZO-CDim 1 bearing azobenzene as a linker and exhibiting high solubility in water. The photoisomerization properties were studied by UV–vis and HPLC and supported by ab initio calculations. The cis/trans ratio of AZO-CDim 1 is 7:93 without irradiation and 37:63 after 120 min of irradiation at 365 nm; the reaction is reversible after irradiation at 254 nm. The photoinduced, switchable binding behavior of AZO-CDim 1 was evaluated by ITC, NMR and molecular modeling in the presence of a ditopic adamantyl guest. The results indicate that AZO-CDim 1 can form two different inclusion complexes with an adamantyl dimer depending on its photoinduced isomers. Both cavities of cis-AZO-CDim 1 are complexed simultaneously by two adamantyl units of the guest forming a 1:1 complex while trans-AZO-CDim 1 seems to lead to the formation of supramolecular polymers with an n:n stoichiometry.

  这篇论文报告了一种有效的桥式双β-CD AZO-CDim 1的制备方法，其中含有偶氮苯作为连接剂，并在水中具有高溶解度。通过UV-vis和HPLC进行了光异构化性能研究，并通过从头计算进行了支持。未经照射时，AZO-CDim 1的顺/反比为7:93，在365 nm照射120分钟后为37:63；254 nm照射后反应可逆。在存在二元脂肪环客体的情况下，通过ITC、NMR和分子建模评估了AZO-CDim 1的光诱导可切换结合行为。结果表明，AZO-CDim 1可以形成两种不同的包含复合物，取决于其光诱导异构体。顺-AZO-CDim 1的两个腔同时与两个客体的脂肪环单体形成1:1复合物，而反-AZO-CDim 1似乎导致与n:n化学计量比的超分子聚合物形成。
• Thermodynamics of Formation of Host−Guest Supramolecular Polymers
  作者：Victor Hugo Soto Tellini、Aida Jover、Jorge Carrazana García、Luciano Galantini、Francisco Meijide、José Vázquez Tato

  DOI：10.1021/ja0572809

  日期：2006.5.1

  The interactions between three beta-cyclodextrin hosts (having 1-3 binding sites) and two adamantyl guests (having 1-2 binding sites) have been studied by ITC, ROESY, static and dynamic light scattering (SLS and DLS), and AFM and TEM techniques. The enthalpy and free energy values (determined from ITC experiments) evidence that the single interaction between one binding site of the guest and one binding site of the host is independent of the number of binding sites of the interacting species. The average values are Delta H degrees = -26.6 +/- 2.3 kJ mol(-1) and Delta G degrees = -30.4 +/- 3.2 kJ mol(-1), indicating that the process is mainly enthalpy driven. In all cases, the experimental molar ratio (from ITC experiments) agrees with the expected one from the number of binding sites of both the host and guest. The formation of polymer-like entities was demonstrated by SLS, DLS, AFM, and TEM measurements. The structure of polymers is linear when both the host and the guest are ditopic entities and dendritic (or Cayley tree type) when the host and the guest have three and two binding sites, respectively.