bis<2,6-di(acetylamino)phenyl> disulfide | 164853-83-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: bis<2,6-di(acetylamino)phenyl> disulfide
• 英文别名: bis(2,6-bis(acetylamino)phenyl) disulfide；bis(2,6-(diacetylamino)phenyl) disulfide；[2,6-bis(acetylamino)phenyl] disulfide；N-[3-acetamido-2-[(2,6-diacetamidophenyl)disulfanyl]phenyl]acetamide
• CAS: 164853-83-2
• 化学式: C₂₀H₂₂N₄O₄S₂
• 分子量: 446.551
• InChiKey: LGTSBABVPCTYQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  167
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  bis(tetraethylammonium)-bis[di-(thiophenolato)-(μ-sulfido)ferrate(III)] 、 bis<2,6-di(acetylamino)phenyl> disulfide 以 乙腈 为溶剂， 以73%的产率得到(NEt4)2[Fe2S2(S-2,6-(CH3CONH)2C6H3)4]
  参考文献：
  名称：

  Structure and Properties of [Fe₄S₄{2,6-bis(acylamino)benzenethiolato-S}₄]^2- and [Fe₂S₂{2,6-bis(acylamino)benzenethiolato-S}₄]^2-:  Protection of the Fe−S Bond by Double NH···S Hydrogen Bonds

  摘要：

  Iron-sulfur clusters containing a singly or doubly NH...S hydrogen-bonded arenethiolate ligand, [Fe4S4(S-2-RCONHC(6)H(4))(4)](2-) (R = CH3, t-Bu, CF3), [Fe4S4{S-2,6-(RCONH)(2)C6H3}(4)](2-), [Fe2S2(S-2-RCONHC(6)H(4))(4)](2-) (R = CH3, t-Bu, CF3), and [Fe2S2{S-2,6-(RCONH)(2)C6H3}(4)](2-), were synthesized as models of bacterial [4Fe-4S] and plant-type [2Fe-2S] fenedoxins. The X-ray structures and IR spectra of (PPh(4))(2)[Fe4S4{S-2,6-(CH3-CONH)(2)C6H3}(4)]. 2CH(3)CN and (NEt(4))(2)[Fe2S2{S-2,6-(t-BuCONH)(2)C6H3}(4)] indicate that the two amide NH groups at the o,o'-positions are directed to the thiolate sulfur atom and form double NH...S hydrogen bonds. The NH...S hydrogen bond contributes to the positive shift of the redox potential of not only (Fe4S4)(+)/(Fe4S4)(2+) but also (Fe4S4)(2+)/(Fe4S4)(3+) in the [4Fe-4S] clusters as well as (Fe2S2)(2+)/(Fe2S2)(3+) in the [2Fe-2S] clusters. The doubly NH...S hydrogen-bonded thiolate ligand effectively prevents the ligand exchange reaction by benzenethiol because the two amide NH groups stabilize the thiolate by protection from dissociation.

  DOI：

  10.1021/ic9604324
• 作为产物：
  描述：

  bis(2,6-diaminophenyl) disulfide 、 乙酸酐 反应 1.0h， 以70%的产率得到bis<2,6-di(acetylamino)phenyl> disulfide
  参考文献：
  名称：

  Crystal and Solution Structures of Novel Bulky Bis[2,6-bis(acylamino)phenyl] Disulfides. Absence of Covalent NH.cntdot..cntdot..cntdot.S Hydrogen Bond between Amide NH and Neighboring Disulfide in Bis[2,6-bis(pivaloylamino)phenyl] Disulfide

  摘要：

  Novel bulky bis[2,6-di(acylamino)phenyl] disulfides, e.g. bis[2,6-di(pivaloylamino)phenyl] disulfide and bis[2,6-di(triphenylacetylamino)phenyl] disulfide, having two acylamino groups at the 2,6-positions of the benzene ring were synthesized and the crystal structures determined. The two bulky acylamino groups cover the disulfide group, and the two amide NH groups are directed toward the sulfur atom, but the IR NH bands observed in the solid state indicate the absence of covalent NH-S hydrogen bonds in bis[2, 6-di(pivaloylamino)phenyl] disulfide.

  DOI：

  10.1021/jo00120a037

文献信息

• Novel Rubredoxin Model Tetrathiolato Iron(II) and Cobalt(II) Complexes Containing Intramolecular Single and Double NH···S Hydrogen Bonds
  作者：Taka-aki Okamura、Satoshi Takamizawa、Norikazu Ueyama、Akira Nakamura

  DOI：10.1021/ic970640b

  日期：1998.1.1

  positive shifted Fe(III)/Fe(II) redox couples by the single and double NH.S hydrogen bond, respectively. The shifts are +0.25 for 2a and +0.56 for 6a from the redox potential of [Fe(II)(SPh)(4)](2-), which indicate additivity of the effect of the NH.S hydrogen bond. The formation and the structure of a novel chelating amido(thiolato) complex (PPh(4))(2)[Co(II)S-2,6-(CF(3)CONH)(2)C(6)H(3)}(2)(S-2-CF(3

  合成了具有邻-（酰基氨基）苯硫醇基和2,6-（二酰基氨基）苯硫醇基的简单的氧化还原蛋白模型配合物，并通过（1）H NMR，IR和电化学性质进行了表征。（NEt（4））（2）[Fe（II）（Sot-BuCONHC（6）H（4））（4）]。2EtCN（3a），（NEt（4））（2）[Co （II）（Sot-BuCONHC（6）H（4））（4）]。2EtCN（3b）和（PPh（4））（2）[Co（II）S-2,6-（CF（ 3）CONH）（2）C（6）H（3）}（4）]。通过X射线分析确定Et（2）O（5b'）。该配合物具有分子内的单或双NH.S氢键。Fe-S和Co-S的平均距离明显短于非氢键配合物[M（SPh）（4）]（2-）（M = Fe（II），Co（II）），分别为0.024Å（3a），0.032Å（3b）和0.029Å（5b'）。（NMe（4））（2）[Fe（II）（So-CH（3）
• Effect of the NH---S Hydrogen Bond on the Nature of Hg−S Bonding in Bis[2-(acylamino)benzenethiolato]mercury(II) and Bis[2,6-bis(acylamino)benzenethiolato]mercury(II) Complexes
  作者：Norikazu Ueyama、Kaku Taniuchi、Taka-aki Okamura、Akira Nakamura、Hironobu Maeda、Shuichi Emura

  DOI：10.1021/ic950472s

  日期：1996.1.1

  2-(Acylamino)benzenethiolate complexes of Hg(II) having an intramolecular NH-S hydrogen bond, Hg[2-(pivaloylamino)benzenethiolato](2) and Hg[2,6-bis(pivaloylamino)benzenethiolato](2), were synthesized and the crystal structures were determined. The crystal structure of Hg[2-(pivaloylamino)benzenethiolato](2) . 1/2H(2)O shows the presence of two distinct conformers with different C-S-(Hg)-S-C torsion angles (81.7 and 176.6 degrees). The crystal structure of Hg[2,6-bis(pivaloylamino)benzenethiolato](2) indicates the presence of ordinary Hg-S bonds (2.335(2) and 2.342(2) Angstrom) and a straight linear coordination (S-Hg-S = 174.7(1)degrees) with a weak interaction of one of the amide CO groups toward HE(II). A weak NH-S hydrogen bond in both complexes is detected from the IR spectra in the solid state. The Hg-199 NMR spectra show the high-field shift with a decrease in the S --> Hg(II) ligand-to-metal charge transfer by the NH-S hydrogen bonding. The high-field shift by the double NH-S hydrogen bond is far greater than that by the p-substituent effect of the electron-withdrawing group (OMe, H, NHCOCH3, Cl, NO2) on the benzenethiolate ring.
• Cytochrome P-450 Model (Porphinato)(thiolato)iron(III) Complexes with Single and Double NH···S Hydrogen Bonds at the Thiolate Site
  作者：Norikazu Ueyama、Nami Nishikawa、Yusuke Yamada、Taka-aki Okamura、Akira Nakamura

  DOI：10.1021/ja9622970

  日期：1996.1.1
• Ueyama, Norikazu; Nishikawa, Nami; Yamada, Yusuke, Inorganic Chemistry, 1998, vol. 37, # 10, p. 2415 - 2421
  作者：Ueyama, Norikazu、Nishikawa, Nami、Yamada, Yusuke、Okamura, Taka-Aki、Oka, Shigenori、Sakurai, Hiromu、Nakamura, Akira

  DOI：——

  日期：——
• Structure and Properties of [Fe₄S₄{2,6-bis(acylamino)benzenethiolato-<i>S</i>}₄]²^- and [Fe₂S₂{2,6-bis(acylamino)benzenethiolato-<i>S</i>}₄]²^-:  Protection of the Fe−S Bond by Double NH···S Hydrogen Bonds
  作者：Norikazu Ueyama、Yusuke Yamada、Taka-aki Okamura、Shuuji Kimura、Akira Nakamura

  DOI：10.1021/ic9604324

  日期：1996.1.1

  Iron-sulfur clusters containing a singly or doubly NH...S hydrogen-bonded arenethiolate ligand, [Fe4S4(S-2-RCONHC(6)H(4))(4)](2-) (R = CH3, t-Bu, CF3), [Fe4S4S-2,6-(RCONH)(2)C6H3}(4)](2-), [Fe2S2(S-2-RCONHC(6)H(4))(4)](2-) (R = CH3, t-Bu, CF3), and [Fe2S2S-2,6-(RCONH)(2)C6H3}(4)](2-), were synthesized as models of bacterial [4Fe-4S] and plant-type [2Fe-2S] fenedoxins. The X-ray structures and IR spectra of (PPh(4))(2)[Fe4S4S-2,6-(CH3-CONH)(2)C6H3}(4)]. 2CH(3)CN and (NEt(4))(2)[Fe2S2S-2,6-(t-BuCONH)(2)C6H3}(4)] indicate that the two amide NH groups at the o,o'-positions are directed to the thiolate sulfur atom and form double NH...S hydrogen bonds. The NH...S hydrogen bond contributes to the positive shift of the redox potential of not only (Fe4S4)(+)/(Fe4S4)(2+) but also (Fe4S4)(2+)/(Fe4S4)(3+) in the [4Fe-4S] clusters as well as (Fe2S2)(2+)/(Fe2S2)(3+) in the [2Fe-2S] clusters. The doubly NH...S hydrogen-bonded thiolate ligand effectively prevents the ligand exchange reaction by benzenethiol because the two amide NH groups stabilize the thiolate by protection from dissociation.