6,8-Dithia-7-selena-3,11-diazabicyclo[11.3.1]heptadeca-1(17),13,15-triene-2,12-dione | 1590421-48-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: 6,8-Dithia-7-selena-3,11-diazabicyclo[11.3.1]heptadeca-1(17),13,15-triene-2,12-dione
• 英文别名: 6,8-dithia-7-selena-3,11-diazabicyclo[11.3.1]heptadeca-1(17),13,15-triene-2,12-dione
• CAS: 1590421-48-9
• 化学式: C₁₂H₁₄N₂O₂S₂Se
• 分子量: 361.347
• InChiKey: KEOPOKITUVPREH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.16
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N,N'-二(2-巯基乙基)间苯二甲酰胺 在 盐酸 、 sodium selenite 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 6,8-Dithia-7-selena-3,11-diazabicyclo[11.3.1]heptadeca-1(17),13,15-triene-2,12-dione 、 6,7-Dithia-3,10-diazabicyclo[10.3.1]hexadeca-1(16),12,14-triene-2,11-dione
  参考文献：
  名称：

  Removal of Selenite from Water Using a Synthetic Dithiolate: An Experimental and Quantum Chemical Investigation

  摘要：

  Combination of the dithiol N,N '-bis(2-mercaptoethyl)isophthalamide, abbreviated as BDTH2 and as 1, with excess H2SeO3 in aqueous acidic (pH approximate to 1) conditions resulted in precipitation of BDT(S-Se-S) (6), with a Se-77 NMR chemical shift of delta = 675 ppm, and oxidized BDT. When the reaction is conducted under basic conditions Se(IV) is reduced to red Se(0) and oxidized 1. No reaction takes place between 1 and selenate (Se(VI)) under acidic or basic conditions. Compound 6 is stable in air but decomposes to red Se(0) and the disulfide BDT(S-S) (9) with heating and in basic solutions. Mechanisms and energetics of the reactions leading to 6 in aqueous solution were unraveled by extensive calculations at the omega B97X-D/aug-cc-pVTZ-PP level of theory. NMR chemical shift calculations with the gauge-independent atomic orbital (GIAO) method for dimethyl sulfoxide as solvent confirm the generation of 6 (calculated delta value = 677 ppm). These results define the conditions and limitations of using 1 for the removal of selenite from wastewaters. Compound 6 is a rare example of a bidentate selenium dithiolate and provides insight into biological selenium toxicity.

  DOI：

  10.1021/ic402909t

文献信息

• Removal of Selenite from Water Using a Synthetic Dithiolate: An Experimental and Quantum Chemical Investigation
  作者：Daniel Burriss、Wenli Zou、Dieter Cremer、John Walrod、David Atwood

  DOI：10.1021/ic402909t

  日期：2014.4.21

  Combination of the dithiol N,N '-bis(2-mercaptoethyl)isophthalamide, abbreviated as BDTH2 and as 1, with excess H2SeO3 in aqueous acidic (pH approximate to 1) conditions resulted in precipitation of BDT(S-Se-S) (6), with a Se-77 NMR chemical shift of delta = 675 ppm, and oxidized BDT. When the reaction is conducted under basic conditions Se(IV) is reduced to red Se(0) and oxidized 1. No reaction takes place between 1 and selenate (Se(VI)) under acidic or basic conditions. Compound 6 is stable in air but decomposes to red Se(0) and the disulfide BDT(S-S) (9) with heating and in basic solutions. Mechanisms and energetics of the reactions leading to 6 in aqueous solution were unraveled by extensive calculations at the omega B97X-D/aug-cc-pVTZ-PP level of theory. NMR chemical shift calculations with the gauge-independent atomic orbital (GIAO) method for dimethyl sulfoxide as solvent confirm the generation of 6 (calculated delta value = 677 ppm). These results define the conditions and limitations of using 1 for the removal of selenite from wastewaters. Compound 6 is a rare example of a bidentate selenium dithiolate and provides insight into biological selenium toxicity.