18-crown-6 compound with glycine (1:1) | 138272-58-9

• 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: 18-crown-6 compound with glycine (1:1)
• 英文别名: 18-crown-6*glycine 1/1；18-crown-6 glycine complex
• CAS: 138272-58-9
• 化学式: C₂H₅NO₂*C₁₂H₂₄O₆
• 分子量: 339.386
• InChiKey: AYICWVIBVCXWNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.87
• 重原子数：
  23.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  118.7
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  18-冠醚-6 、 聚甘氨酸 以 三氟乙酸 为溶剂， 生成 18-crown-6 compound with glycine (1:1)
  参考文献：
  名称：

  Complex formation of crown ethers with α-amino acids: Estimation by NMR spectroscopy

  摘要：

  Complex formation of 18-crown-6 and dibenzo crowns with glycine, leucine, and norleucine was studied by NMR spectroscopy. The efficiency of non-valence interactions with participation of different active centers of the host and guest molecules is determined by solvation effects, mutual arrangement of benzene rings in dibenzo crowns, and the presence of bulky aliphatic substituents in the alpha-amino acid. The complexation of dibenzo crowns with alpha-amino acids in acid medium involves a system of different non-valence interactions, the most efficient of which are NH (3) (+) ... O hydrogen bond between the ammonium group in the guest molecule and ether oxygen atoms in the host molecule and dipole-dipole interaction between the guest ammonium group and host benzene ring (NH (3) (+) ... Ar). The efficiency of NH (3) (+) ... O hydrogen bonding decreases in going from 18-crown-6 to dibenzo crowns due to distortion of symmetry of the macroring cavity and violation of geometric complementarity of some ether oxygen atoms. The integral efficiency of non-valence interactions in the system dibenzo crown-alpha-amino acid was estimated on a quantitative level by H-1 NMR relaxation technique.

  DOI：

  10.1134/s1070428013090261

文献信息

• Effect of solvation on the thermodynamics of the formation of molecular complexes of 18-crown-6 ether with glycine in water-dimethylsulfoxide solutions
  作者：T. R. Usacheva、V. A. Sharnin、E. Matteoli

  DOI：10.1134/s003602441111032x

  日期：2011.11

  Complexation of the 18-crown-6 ether (18C6) with glycine (Gly) in mixed H(2)O-DMSO solvents with the composition of 0.1, 0.2, and 0.25 mole fraction of DMSO (T = 298.15 K) was studied calorimetrically. Thermodynamic characteristics of the reaction of the formation of the molecular Gly18C6 complex (Delta(r) GA degrees, Delta(r) HA degrees, T Delta(r) SA degrees) were calculated from the calorimetric data. It was established that the change in the stability of the Gly18C6 complex is mainly determined by the predominance of the enthalpy component of the Gibbs energy over the entropy component. It was shown during the analysis of the enthalpy contributions of the reagents to the enthalpy of the reaction of the formation of Gly18C6 that the change in the enthalpy of the reaction upon a change the solvent composition was due to changes in the solvation state of 18C6.
• Formation of molecular complexes between 18-crown-6 and amino acids in aqueous-organic media
  作者：T. R. Usacheva、V. A. Sharnin

  DOI：10.1134/s1070363214020121

  日期：2014.2

  Data on the effect of aqueous-organic solvent composition on molecular complexes formation of 18-crown-6 with glycine, D,L-alanine, and L-phenylalanine have been generalized. The inncrease in ethanol, dimethylsulfoxide, or acetone fraction enhances the complexes stability. Amino acid solvation gives the major impact on the Gibbs free energy of complexes formation. It was demonstrated that stability of 18-crown-6 complexes with amino acids could be predicted basing on changes of the amino acid solvation state.