1,1',5,5'-Tetramethyl-6,6'-dioxo-3,3'-biverdazyl diradical | 74809-05-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,1',5,5'-Tetramethyl-6,6'-dioxo-3,3'-biverdazyl diradical
• 英文别名: 1,1',5,5'-tetramethyl-6,6'-dioxo-3,3'-bisverdazyl；1,1',5,5'-Tetramethyl-6,6'-dioxo-3,3'-biverdazyl；1,1',5,5'-tetramethyl-6,6'-dioxobis(verdazyl)；6-(1,5-Dimethyl-6-oxo-1,2,4,5-tetrazin-1-ium-3-yl)-2,4-dimethyl-1,2,4-triaza-5-azanidacyclohex-6-en-3-one
• CAS: 74809-05-5
• 化学式: C₈H₁₂N₈O₂
• 分子量: 252.236
• InChiKey: AAOGZZUHYXTKMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  85
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,1',5,5'-Tetramethyl-6,6'-dioxo-3,3'-biverdazyl diradical 在 Pd-BaSO₄ 氢气 作用下， 以 甲醇 、 水 为溶剂， 以48%的产率得到4,4',5,5'-Tetrahydro-1,1',5,5'-tetramethyl<3,3'-bi-1,2,4,5-tetrazin>-6,6'(1H,1'H)-dion
  参考文献：
  名称：

  Neugebauer, Franz A.; Fischer, Hans; Siegel, Rolf, Chemische Berichte, 1988, vol. 121, p. 815 - 823

  摘要：

  DOI：
• 作为产物：
  描述：

  2,2',3,3',4,4',5,5'-Octahydro-1,1',5,5'-tetramethyl<3,3'-bi-1,2,4,5-tetrazin>-6,6'-(1H,1'H)-dion 在 sodium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 水 为溶剂， 反应 3.0h， 以56%的产率得到1,1',5,5'-Tetramethyl-6,6'-dioxo-3,3'-biverdazyl diradical
  参考文献：
  名称：

  Neugebauer, Franz A.; Fischer, Hans; Siegel, Rolf, Chemische Berichte, 1988, vol. 121, p. 815 - 823

  摘要：

  DOI：

文献信息

• Neugebauer, Franz A.; Fischer, Hans, Angewandte Chemie, 1980, vol. 92, # 9, p. 766
  作者：Neugebauer, Franz A.、Fischer, Hans

  DOI：——

  日期：——
• Electronic Interactions in Verdazyl Biradicals
  作者：Rosario M. Fico、Michael F. Hay、Scott Reese、Steve Hammond、Elizabeth Lambert、Marye Anne Fox

  DOI：10.1021/jo990962s

  日期：1999.12.1

  A series of bisverdazyl biradicals in which the atoms bearing the greatest spin density are separated by several different aromatic spacer groups has been prepared in order to compare their properties to those of the nonspaced 1,1',5,5'-tetramethy1-6,6'-dioxo-3,3'-bisverdazyl (1). In addition, the 6,6'-dithio derivative (1,1',5,5'-tetramethyl-6,6'-dithio-3,3'-bis (7)) was prepared. Cyclic voltammograms of 1,4-bis(1,5-dimethyl-6-oxo-5-verdazyl)benzene (5) and 2,5-bis(1,5-dimethyl-6-oxo-3-verdazyl)thiophene (6) both show a single two-electron oxidation near 700 mV. In contrast 1, 7, and 1,3-bis(1,5-dimethyl-6-oxo-3-verdazyl)benzene (4) display two one-electron oxidation waves, with the first oxidative wave appearing also near 700 mV. The absorption spectrum of each of these biradicals was red-shifted from the maximum observed for 1. Biradicals 4, 5, and 6 exhibited linear Curie plots, although a curved Curie plot was observed for 7 with J = 560 cm(-1).
• Spin Delocalization in the Copper(I) Complexes of Bis(verdazyl) Diradicals
  作者：David J. R. Brook、Vincent Lynch、Brenda Conklin、Marye Anne Fox

  DOI：10.1021/ja961675y

  日期：1997.6.1

  1,2',5,5'-tetramethyl-6,6'-dioxobis(verdazyl) (BVD) reacts with copper(I) halides in acetonitrile and copper(II) halides in methanol to give copper(I) coordination polymers of composition [Cu2X2(BVD)]. When X = Cl and X = Br, these polymers crystallize in orthorhombic unit cells with dimensions a = 6.684(1) Angstrom, b = 12.524(3) Angstrom, and c = 8.717(2) a (X = Cl) and a 12.680(2) Angstrom, b = 6.744(1) Angstrom, and c = 8.822(2) Angstrom (X = Br). With X = I, powder diffraction indicates a monoclinic unit cell with dimensions a = 12.669 Angstrom, b = 8.461 Angstrom, c = 7.679 Angstrom, and beta = 91.88 degrees, although poor crystal quality prevented a full structure determination. Magnetic susceptibility measurements taken on the three polymers indicate that the spins couple in one-dimensional chains with alternating exchange parameters: J(1) = -190 cm(-1), J(2) = -116 cm(-1) (X = Cl); J(1) = -200 cm(-1), J(2) = -110 cm(-1) (X = Br); and J(1) = -271 cm(-1), J(2) = -200 cm(-1) (X = I). Variable temperature ESR measurements on the unstable monomeric complex resulting from reaction of BVD with (CH3O)(3)PCuI indicate an interradical exchange parameter J of -230 cm(-1). ESR spectra of all three complexes show extremely broad, featureless lines as a result of very rapid spin-cm(-1). lattice relaxation. The reduction in exchange between the two halves of the bis(verdazyl)ligand upon coordination, and the unusual ESR properties, require a delocalized structure, with significant spin density on the copper atom. Variation of the auxiliary ligands on the copper atom allows tuning of the intramolecular exchange.
• NEUGEBAUER F. A.; FISCHER H., ANGEW. CHEM., 1980, 92, NO 9, 766
  作者：NEUGEBAUER F. A.、 FISCHER H.

  DOI：——

  日期：——
• NEUGEBAUER, FRANZ A.;FISCHER, HANS;SIEGEL, ROLF, CHEM. BER., 121,(1988) N 5, 815-822
  作者：NEUGEBAUER, FRANZ A.、FISCHER, HANS、SIEGEL, ROLF

  DOI：——

  日期：——