2,3,7,8-Tetramethoxyselenanthren | 50499-86-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硒蒽
• 英文名称: 2,3,7,8-Tetramethoxyselenanthren
• 英文别名: 2,3,7,8-tetramethoxyselenanthrene；Selenanthrene, 2,3,7,8-tetramethoxy-
• CAS: 50499-86-0
• 化学式: C₁₆H₁₆O₄Se₂
• 分子量: 430.221
• InChiKey: RYTMZQYCULTDRR-UHFFFAOYSA-N

物化性质

• 沸点：
  504.7±60.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.66
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3,7,8-Tetramethoxyselenanthren 在 碘 作用下， 以 正己烷 、 甲苯 为溶剂， 生成 2,3,6,7-tetramethoxyselenananthren-radikalkation trijodid
  参考文献：
  名称：

  EINKRISTALL-MOLEKÜLSTRUKTUREN 107^1.2: STRUKTURÄNDERUNGEN VON THIANTHREN, 2,3,6,7-TETRAMETHOXYTHIANTHREN UND 2,3,6,7-TETRAMETHOXYSELENANTHREN BEI KOMPLEXBILDUNG MIT ELEKTRONENAKZEPTOREN SOWIE BEI EINELEKTRONENOXIDATION ZU DEN RADIKALKATIONEN

  摘要：

  Information on structural changes due to partial and full one-electron transfer is obtained by comparing the single crystal structures of both donor/acceptor complexes of thianthrene and selenanthrene derivatives with those of their radical cation salts: The single crystal structures of {thianthrene ... pyromelliticdianhydride}, {2,3,6,7-tetramethoxythianthrene ... 1,2,4,5-tetracyanobenzene} and 2,3,6,7-tetramethoxyselenanthrene ... 1,2,4,5-tetracyanobenzene} do not exhibit any significant differences relative to that of their components. On the contrary, in the corresponding radical cation salts [2,3,6,7-tetramethoxythianthrene(.+)][Br-3(-)] as well as [2,3,6,7-tetramethoxyselenanthrene(.+)][I-3(-)] severe structural changes are observed such as the flattening of the molecular skeletons or beginning cyanine distortions along the chains H3CO-C-3-X-C-3-OCH3. Accompanying UV/VIS measurements of solutions containing both donor and acceptor prove long-wavelengths charge transfer bands with drastically reduced excitation energies relative to that of the separated molecules. Therefore, in the ground state of the donor/acceptor complexes between electron-rich sulfur donors and suitable accepters, only an almost negligible charge transfer occurs. The weak interactions in the van der Waals complexes can be rationalized by correlation of the respective orbital diagrams with the crystal lattice arrangements determined experimentally. Altogether, prospects for new materials are provided.

  DOI：

  10.1080/10426509608037954
• 作为产物：
  描述：

  邻苯二甲醚 在 selenium(IV) oxide 作用下， 以 水 为溶剂， 以4.8 g的产率得到2,3,7,8-Tetramethoxyselenanthren
  参考文献：
  名称：

  EINKRISTALL-MOLEKÜLSTRUKTUREN 107^1.2: STRUKTURÄNDERUNGEN VON THIANTHREN, 2,3,6,7-TETRAMETHOXYTHIANTHREN UND 2,3,6,7-TETRAMETHOXYSELENANTHREN BEI KOMPLEXBILDUNG MIT ELEKTRONENAKZEPTOREN SOWIE BEI EINELEKTRONENOXIDATION ZU DEN RADIKALKATIONEN

  摘要：

  Information on structural changes due to partial and full one-electron transfer is obtained by comparing the single crystal structures of both donor/acceptor complexes of thianthrene and selenanthrene derivatives with those of their radical cation salts: The single crystal structures of {thianthrene ... pyromelliticdianhydride}, {2,3,6,7-tetramethoxythianthrene ... 1,2,4,5-tetracyanobenzene} and 2,3,6,7-tetramethoxyselenanthrene ... 1,2,4,5-tetracyanobenzene} do not exhibit any significant differences relative to that of their components. On the contrary, in the corresponding radical cation salts [2,3,6,7-tetramethoxythianthrene(.+)][Br-3(-)] as well as [2,3,6,7-tetramethoxyselenanthrene(.+)][I-3(-)] severe structural changes are observed such as the flattening of the molecular skeletons or beginning cyanine distortions along the chains H3CO-C-3-X-C-3-OCH3. Accompanying UV/VIS measurements of solutions containing both donor and acceptor prove long-wavelengths charge transfer bands with drastically reduced excitation energies relative to that of the separated molecules. Therefore, in the ground state of the donor/acceptor complexes between electron-rich sulfur donors and suitable accepters, only an almost negligible charge transfer occurs. The weak interactions in the van der Waals complexes can be rationalized by correlation of the respective orbital diagrams with the crystal lattice arrangements determined experimentally. Altogether, prospects for new materials are provided.

  DOI：

  10.1080/10426509608037954

文献信息

• Gunsser, W.; Henning, J. H.; Klar, G., Berichte der Bunsen-Gesellschaft, 1989, vol. 93, p. 1370 - 1373
  作者：Gunsser, W.、Henning, J. H.、Klar, G.、Martinez, E. Sanchez

  DOI：——

  日期：——
• Preparation and Interconversion of Phenylselenenylated and Alkylselenenylated Aromatic Compounds
  作者：Lars Engman、Per Eriksson

  DOI：10.3987/com-95-7377

  日期：——

  Phenylselenenyl and alkylselenenyl sulfates were found to efficiently and mildly introduce one or several phenylselenenyl or alkylselenenyl groups into activated aromatic or heteroaromatic compounds. When treated with methylselenenyl sulfate, veratrole and 2,2',3,3'-tetramethoxybiphenyl afforded 2,3,7,8-tetramethoxyselenanthrene and 2,3,7,8-tetramethoxy-dibenzoselenophene, respectively, via oxidative demethylation at selenium/cyclization. Phenyl-selenenylated thiophenes were selectively hydrodeselenenated at the 2- and/or 5-positions by treatment with the appropriate amount of n-butyllithium at -78 degrees C followed by hydrolysis.
• Hinrichs, Winfried; Berges, Peer; Klar, Guenter, Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1986, vol. 41, # 9, p. 1133 - 1141
  作者：Hinrichs, Winfried、Berges, Peer、Klar, Guenter、Sheldrick, George M.

  DOI：——

  日期：——
• Berges, Peer; Kudnig, Jens; Klar, Guenter, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1989, vol. 44, # 2, p. 211 - 219
  作者：Berges, Peer、Kudnig, Jens、Klar, Guenter、Martinez, Enrique Sanchez、Calleja, Ricardo Diaz

  DOI：——

  日期：——
• Berges, Peer; Hinrichs, Winfried; Klar, Guenter, Journal of Chemical Research, Miniprint, 1986, # 10, p. 3121 - 3136
  作者：Berges, Peer、Hinrichs, Winfried、Klar, Guenter

  DOI：——

  日期：——

表征谱图