hexamethylated p-sulfonatocalix[6]arene

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: hexamethylated p-sulfonatocalix[6]arene
• 英文别名: 37,38,39,40,41,42-Hexamethoxyheptacyclo[31.3.1.13,7.19,13.115,19.121,25.127,31]dotetraconta-1(36),3,5,7(42),9,11,13(41),15,17,19(40),21(39),22,24,27(38),28,30,33(37),34-octadecaene-5,11,17,23,29,35-hexasulfonate；37,38,39,40,41,42-hexamethoxyheptacyclo[31.3.1.13,7.19,13.115,19.121,25.127,31]dotetraconta-1(36),3,5,7(42),9,11,13(41),15,17,19(40),21(39),22,24,27(38),28,30,33(37),34-octadecaene-5,11,17,23,29,35-hexasulfonate
• 化学式: C₄₈H₄₂O₂₄S₆
• 分子量: 1195.24
• InChiKey: LHAQWNAEELSKBZ-UHFFFAOYSA-H

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  78
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  449
• 氢给体数：
  0
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  百草枯 、 hexamethylated p-sulfonatocalix[6]arene 在 sodium chloride 作用下， 以 重水 为溶剂， 生成
  参考文献：
  名称：

  Host Properties of α-Cyclodextrin and a Water-Soluble Calix[6]arene Probed with Dimeric Bipyridinium Guests

  摘要：

  The complexation properties of two complementary hosts, a-cyclodextrin and a water-soluble sulfonated calixarene, with dimeric viologen guests, in which the viologen units are linked by an undecyl chain, have been investigated. While the complexation behavior of the cyclodextrin host is driven by hydrophobic interactions, that of the calixarene is largely electrostatic in nature. Both hosts show high affinity for the viologen guests, but for completely different reasons. H-1 NMR spectroscopic evidence demonstrates the inclusion complexation of the alkyl chain connecting the two viologen subunits by the hydrophobic cyclodextrin cavity. This interaction is strongly pH dependent, and the complexation can be switched by protonating the two unquaternized nitrogen atoms of the guest, thereby making it more hydrophilic and resulting in partial unthreading of the cyclodextrin host. Calorimetric data shows the association constant to be quite high and the complexation to be enthalpically driven, in accord with nonclassical hydrophobic interactions. Cyclic voltammetric experiments demonstrate the solubilization of the reduced viologen form by the cyclodextrin, lessening its deposition on the electrode surface. The strong electrostatically driven association between the cationic viologen guests and the hexaanionic calixarene host was also examined. The binding constants determined from NMR data were on the order of 10(3) M-l. The data suggest that these complexes are also of the inclusion type. Unlike alpha-CD, calixarene complexation makes the guests more prone to deposit on the electrode surface during voltammetric experiments.

  DOI：

  10.1021/jo9701997

文献信息

• Host Properties of α-Cyclodextrin and a Water-Soluble Calix[6]arene Probed with Dimeric Bipyridinium Guests
  作者：René Castro、Luis A. Godínez、Cecil M. Criss、Angel E. Kaifer

  DOI：10.1021/jo9701997

  日期：1997.7.1

  The complexation properties of two complementary hosts, a-cyclodextrin and a water-soluble sulfonated calixarene, with dimeric viologen guests, in which the viologen units are linked by an undecyl chain, have been investigated. While the complexation behavior of the cyclodextrin host is driven by hydrophobic interactions, that of the calixarene is largely electrostatic in nature. Both hosts show high affinity for the viologen guests, but for completely different reasons. H-1 NMR spectroscopic evidence demonstrates the inclusion complexation of the alkyl chain connecting the two viologen subunits by the hydrophobic cyclodextrin cavity. This interaction is strongly pH dependent, and the complexation can be switched by protonating the two unquaternized nitrogen atoms of the guest, thereby making it more hydrophilic and resulting in partial unthreading of the cyclodextrin host. Calorimetric data shows the association constant to be quite high and the complexation to be enthalpically driven, in accord with nonclassical hydrophobic interactions. Cyclic voltammetric experiments demonstrate the solubilization of the reduced viologen form by the cyclodextrin, lessening its deposition on the electrode surface. The strong electrostatically driven association between the cationic viologen guests and the hexaanionic calixarene host was also examined. The binding constants determined from NMR data were on the order of 10(3) M-l. The data suggest that these complexes are also of the inclusion type. Unlike alpha-CD, calixarene complexation makes the guests more prone to deposit on the electrode surface during voltammetric experiments.