1,3-Bis(1,3-dihydroxy-4,4,5,5-tetramethylimidazolin-2-yl)-5-ethynylbenzene | 904671-80-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 1,3-Bis(1,3-dihydroxy-4,4,5,5-tetramethylimidazolin-2-yl)-5-ethynylbenzene
• 英文别名: 2-[3-(1,3-Dihydroxy-4,4,5,5-tetramethylimidazolidin-2-yl)-5-ethynylphenyl]-1,3-dihydroxy-4,4,5,5-tetramethylimidazolidine
• CAS: 904671-80-3
• 化学式: C₂₂H₃₄N₄O₄
• 分子量: 418.536
• InChiKey: YNOYFWXDKWUJNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  93.9
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,3-Bis(1,3-dihydroxy-4,4,5,5-tetramethylimidazolin-2-yl)-5-ethynylbenzene 在 四(三苯基膦)钯 manganese(IV) oxide 、 selenium(IV) oxide 、 二异丙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 57.0h， 生成 4,4,5,5-Tetramethyl-2-[3-(4,4,5,5-tetramethyl-1-oxidoimidazol-2-yl)-5-[2-[3-[2-[3-(4,4,5,5-tetramethyl-1-oxidoimidazol-2-yl)-5-(4,4,5,5-tetramethyl-1-oxoimidazol-1-ium-2-yl)phenyl]ethynyl]phenyl]ethynyl]phenyl]imidazol-1-ium 1-oxide
  参考文献：
  名称：

  为了更好地理解间亚苯基α-亚硝酰基硝基氧和亚氨基亚硝基氧基团之间的磁性相互作用，第三部分：基于苯基乙炔和联苯偶合单元的一系列三基和四基的磁性交换。

  摘要：

  本工作完成并扩展了我们先前关于磁性基态的确定以及一系列双基团内部的直键交换耦合的强度的报告。该知识随后被用于分析其晶体中的磁性相互作用。我们在这里报告了一系列三价自由基的研究，其中三价自由基结合了α-亚硝基硝基氧化物（NN）或α-亚氨基亚硝基氧化物（IN）作为在一种情况下通过间亚苯基偶联单元和在另一种情况下通过苯基乙炔单元连接的末端自由基片段。还研究了四价基衍生物。对孤立分子的研究（溶液中的EPR和DFT计算）可以评估通过磁耦合单元进行的磁相互作用。发现所有三基导数都表现出四重基态，而四自由基的单线基态是确定的。最后的结果加强了先前的发现，即在涉及类似间苯撑成色剂的相关双自由基中，单线态基态是有利的。此外，可以将用于邻元连接的贯通键磁交换耦合证明为铁磁的，从而确定了我们先前的假设。三自由基和四自由基在固态时的磁性已经通过使用先前提出的方法进行了合理化，从而可以确定最相关的磁路。可以将用于邻

  DOI：

  10.1002/chem.200400552
• 作为产物：
  描述：

  5-((trimethylsilyl)ethynyl)isophthalaldehyde 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 27.0h， 生成 1,3-Bis(1,3-dihydroxy-4,4,5,5-tetramethylimidazolin-2-yl)-5-ethynylbenzene
  参考文献：
  名称：

  Towards a Better Understanding of the Magnetic Interactions withinm-Phenyleneα-Nitronyl Imino Nitroxide Based Biradicals

  摘要：

  An extensive investigation of the magnetic properties of three series of biradicals (bis-nitronyl nitroxides diNN-R, bis-imino nitroxides diIN-R and mixed INNN-R. where R is either hydrogen, a triple bond or trimethylsilylacetylenic group) has been carried out to give clear values of the intramolecular interactions through the m-phenylene coupling unit with alpha -nitronyl nitroxides (NN) or alpha -imino nitroxides (IN). An EPR study of the molecules in the isolated state is validated by ab initio calculations, which show the respective influence of spin polarisation and molecular conformation on the singlet-triplet gaps. All these results indicate that the triplet state is the ground state for such biradicals. except when the imidazolyl cycles are orthogonal to the phenyl ring. The magnetic properties of the biradicals in the solid state can be rationalised by examination of the short contacts produced between the ONC-NO and ONCN groups. EPR studies on single crystals of the H-substituted series have confirmed the presence of a structural distortion for diNN-H whereas diIN-H and INNN-H do not exhibit such a peculiarity. The magnetic behav lour of diIN-H is described well by a four-spins model, with a strong intermolecular antiferromagnetic interaction of -90 K, whereas in the case of the two other compounds. a supplementary contact involves more complex interactions between the dimers. The compound diNN-tmsa exhibits a ferromagnetic intermolecular interaction of +11 K within the dimers, and this could be attributed to the relative disposition of the imidazolyl rings. Compound diNN-tr reveals a chain-like behaviour, whereas diIN-tr shows a predominant antiferromagnetic interaction within the dimers. The values for the intramolecular interactions in the solid state are in good agreement with those found for the isolated molecules.

  DOI：

  10.1002/1521-3765(20010601)7:11<2466::aid-chem24660>3.0.co;2-4