| 622784-52-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 622784-52-5
• 化学式: C₃₂H₅₀N₄O₄Zn
• 分子量: 620.163
• InChiKey: YIKPFETWDOFRLC-XCSIXQCQSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
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• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为产物：
  描述：

  zinc(II) acetylacetonate 、 N,N'-dineopentyl-2-amino-5-alcoholate-1,4-benzoquinonemonoiminium 以 甲苯 为溶剂， 以80%的产率得到
  参考文献：
  名称：

  A 6π + 6π Potentially Antiaromatic Zwitterion Preferred to a Quinoidal Structure:  Its Reactivity Toward Organic and Inorganic Reagents

  摘要：

  A straightforward synthesis of the zwitterionic benzoquinonemonoimine 8 is reported. This molecule is a rare example of a zwitterion being more stable than its canonical forms. It is shown that 8 is best described as constituted of two chemically connected but electronically not conjugated 6 pi electron subunits. Its reactivity with electrophiles such as H+, CH3+, and metal salts leads to the synthesis of new 12,7 electron molecules 12 (H+), 14 (CH3+), and 20 (Pd2+), respectively, in which one or both 6 pi electron subsystems localize into an alternation of single and double bonds, as established by X-ray diffraction. The acidity of the N-H protons of 8 can be modulated by an external reagent. Dependent on the electrophile used, the control of the pi system delocalization becomes possible. When the electrophile simply adds to the zwitterion as in 12, 14, or 15, there is no more negative charge to be delocalized and only the positive charge remains delocalized between the nitrogen atoms. Furthermore, when a reaction with the electrophilic reagent results in deprotonation, as in 17-21, there remains no charge in the system to be delocalized. DFT calculations were performed on models of 8, 12, 14, 20, and on other related zwitterions 9 and 10 in order to examine the influence of the fused cycles on the charge separation and on the singlet-triplet energy gap. An effect of the nitrogen substituents in 8 is to significantly stabilize the singlet state. The dipole moment of 8 was measured to be 9.7 D in dichloromethane, in agreement with calculated values. The new ligands and complexes described in this article constitute new classes of compounds relevant to many areas of chemistry.

  DOI：

  10.1021/ja0354622