2,1,3-benzothiaselenazolium chloride | 55783-18-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2,1,3-benzothiaselenazolium chloride
• CAS: 55783-18-1
• 化学式: C₆H₄NSSe*Cl
• 分子量: 236.583
• InChiKey: LLADEMOLVMTWRL-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.36
• 重原子数：
  10.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.89
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2,1,3-benzothiaselenazolium chloride 在 三苯基锑 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Experimental and Computational Study on the Structure and Properties of Herz Cations and Radicals: 1,2,3-Benzodithiazolium, 1,2,3-Benzodithiazolyl, and Their Se Congeners

  摘要：

  Salts of 1,2,3-benzodithiazolium (1), 2,1,3-benzothiaselenazolium (3), and 1,2,3-benzodiselenazolium (4) (Herz cations), namely, [1][BF4], [1][SbCl6], [3][BF4], [3][GaCl4], [3][SbCl6], and [4][GaCl4], were prepared from the corresponding chlorides and NaBF4, GaCl3, or SbCl5. It was found that [1][SbCl6] and [3][SbCl6] spontaneously transform in MeCN solution to [1](3)[SbCl6](2)[0] and [3](3)[SbCl6](2)[Cl], respectively. [1][BF4], [1](3)[SbCl6](2)[Cl], [3][BF4], [3](3)[SbCl6](2)[Cl], and [4]-[GaCl4] were structurally characterized by X-ray diffraction (XRD). In solution, these [BF4](-) and [GaCl4](-) salts as well as [1][GaCl4], [2][GaCl4], [3][GaCl4], [3][Cl], and [4][Cl] were characterized by multinuclear nuclear magnetic resonance (NMR). The corresponding Hen radicals 1(center dot)-4(center dot) were obtained in toluene and DCM solutions by the reduction of the appropriate salts with Ph3Sb and characterized by EPR. Cations 1-4 and radicals 1(center dot)-4(center dot) were investigated computationally at the density functional theory (DFT) and second-order Moller-Plesset (MP2) levels of theory. The B1B95/cc-pVTZ method was found to satisfactorily reproduce the experimental geometries of 1-4; an increase in the basis set size to cc-pVQZ results in only minor changes. For both 1-4 and 1(center dot)-4(center dot), the Hirshfeld charges and bond orders, as well as the Hirshfeld spin densities for the radicals, were calculated using the B IB95/cc-pVQZ method. It was found for both the cations and the radicals that replacing S atoms with Se atoms leads to considerable changes in the atomic charges, bond lengths, and bond orders only at the involved and the neighboring sites. According to the calculations, 60% of the positive charge in the cations and 80% of the spin density in the radicals is localized on the heterocycles, with the spin density distributions being very similar for all radicals 1(center dot)-4(center dot). For the cations 1-4, the NICS values (B3LYP/cc-pVTZ for B1B95/cc-pVTZ geometries) lie in the narrow range from -5.5 ppm to -6.6 ppm for the carbocycles, and from -14.4 ppm to -15.5 ppm for heterocycles, clearly indicating the aromaticity of the cations. Calculations on radical dimers [1(center dot)](2)-[4(center dot)](2) revealed, with only one exception, positive dimerization energies, i.e., the dimers are inherently unstable in the gas phase.

  DOI：

  10.1021/ic302203t
• 作为产物：
  描述：

  2-aminoselenophenol hydrochloride 在 氯化亚砜 作用下， 生成 2,1,3-benzothiaselenazolium chloride
  参考文献：
  名称：

  Benzo-2,1,3-thiaselenazolium salts

  摘要：

  DOI：

  10.1007/bf00471410

文献信息

• New 3,1,2,4-benzothiaselenadiazines, related π-heterocycles including Herz cations, radicals and molecular complexes, and Bunte salts
  作者：Alexander Yu. Makarov、Yulia M. Volkova、Samat B. Zikirin、Irina G. Irtegova、Irina Yu. Bagryanskaya、Yuri V. Gatilov、Andrey A. Nefedov、Andrey V. Zibarev

  DOI：10.1039/d1nj05979c

  日期：——

  carbocycle-chlorinated and non-chlorinated 3,3-dioxides of the starting material, which is a rare example of a molecular complex involving a Herz cation. Formation of the dioxides can be explained through intermediate participation of the benzodithiadiazine radical cation. Hydrolysis of 3,1,2,4-benzothiaselenadiazine or 1,3,2,4-benzodithiadiazine led to Se-(2-aminophenyl)selenosulfate (Se-Bunte salt) or

  通过化合物 Ar-N 的亲电环化合成了新的硫属元素-氮 π-杂环化合物，包括 3,1,2,4-苯并噻吩二嗪、1,3,2,4-苯并二噻二嗪和 1,2,4,3,5-苯并三噻二氮杂S N-SiMe 3在 SeCl 2、 SeCl 4 /FeCp 2、SCl 2和 S 2 Cl 2的作用下。获得的杂环被热解成持久的 2,1,3-苯并噻吩唑基和 1,2,3-苯并二噻唑基（Herz 自由基），使用 EPR 光谱和 DFT 计算对其进行了表征。原型 3,1,2,4-苯并噻吩二嗪与 SCl 2的反应得到 2,1,3-苯并噻吩唑氯化物（Herz 盐），而空间位阻 1,3,2,4-苯并二噻二嗪则导致相应的 Herz 盐与意想不到的碳环氯化和非氯化 3,3-起始材料的二氧化硫，这是涉及 Herz 阳离子的分子复合物的罕见例子。可以通过苯并二噻二嗪自由基阳离子的中间参与来解释二氧化物的形成。3,1,2,4-苯并噻吩二嗪或
• Structures and reactivities of benzo-1,2,3-dithiazolium salts and their selenium analogs
  作者：Yu. I. Akulin、M. M. Gel'mont、B. Kh. Strelets、L. S. �fros

  DOI：10.1007/bf00471639

  日期：1978.7