2-mercapto-N-pyridin-2-yl-methylbenzamide | 871916-54-0

• 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: 2-mercapto-N-pyridin-2-yl-methylbenzamide
• 英文别名: N-(pyridin-2-ylmethyl)-2-sulfanylbenzamide
• CAS: 871916-54-0
• 化学式: C₁₃H₁₂N₂OS
• 分子量: 244.317
• InChiKey: JCOVHQXSRDNJRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  43
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  pentaaminechlorocobalt(III) dichloride 、 2-mercapto-N-pyridin-2-yl-methylbenzamide 、 四乙基氯化铵 在 NaH 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以59%的产率得到(Et4N)[Co(2-mercapto-N-pyridin-2-yl-methylbenzamide(2-))2]
  参考文献：
  名称：

  Modeling the Active Site of Nitrile Hydratase:  Synthetic Strategies to Ensure Simultaneous Coordination of Carboxamido-N and Thiolato-S to Fe(III) Centers

  摘要：

  A general strategy for synthesizing Fe(III) complexes of ligands containing carboxamido-N and thiolato-S donors has been described. Reaction of the doubly deprotonated ligand PyPepS(2-) (where PyPepSH(2) = N-2-mercaptophenyl2'-pyridinecarboxamide) with Fe(III) salts in DMF had previously afforded the Fe(III) complex (Et4N)[Fe(PyPePS)(2)] without any problem(s) associated with autoredox reactions of the thiolate functionality. In the present work, similar reactions with the doubly deprotonated ligand PiPepS(2-) (where PiPepSH(2) = 2-mercapto-N-pyridin-2-yl-methylbenzamide) with Fe(III) salts, however, fail to afford any Fe(III) complex because of autoredox reactions. The break in the conjugation in the PiPepSH(2) ligand frame is the key reason for this difference in behavior between these two very similar ligands. This is demonstrated by the fact that the same reaction with AqPepS(2-) (where AqPepSH(2) = 2-mercapto-N-quinolin-8-yl-benzamide), another ligand with extended conjugation, affords the Fe(III) complex (Et4N)[Fe(AqPePS)(2)] (1) without any synthetic complication. It is therefore evident that ligands in which the carboxamide and thiolate functionalities are kept in conjugation could be used to isolate Fe(III) complexes with carboxamido-N and thiolato-S coordination. This finding will be very helpful in future research work in the area of modeling the active site of Fe-containing nitrile hydratase.

  DOI：

  10.1021/ic051183z

文献信息

• Modeling the Active Site of Nitrile Hydratase:  Synthetic Strategies to Ensure Simultaneous Coordination of Carboxamido-N and Thiolato-S to Fe(III) Centers
  作者：Todd C. Harrop、Marilyn M. Olmstead、Pradip K. Mascharak

  DOI：10.1021/ic051183z

  日期：2005.12.1

  A general strategy for synthesizing Fe(III) complexes of ligands containing carboxamido-N and thiolato-S donors has been described. Reaction of the doubly deprotonated ligand PyPepS(2-) (where PyPepSH(2) = N-2-mercaptophenyl2'-pyridinecarboxamide) with Fe(III) salts in DMF had previously afforded the Fe(III) complex (Et4N)[Fe(PyPePS)(2)] without any problem(s) associated with autoredox reactions of the thiolate functionality. In the present work, similar reactions with the doubly deprotonated ligand PiPepS(2-) (where PiPepSH(2) = 2-mercapto-N-pyridin-2-yl-methylbenzamide) with Fe(III) salts, however, fail to afford any Fe(III) complex because of autoredox reactions. The break in the conjugation in the PiPepSH(2) ligand frame is the key reason for this difference in behavior between these two very similar ligands. This is demonstrated by the fact that the same reaction with AqPepS(2-) (where AqPepSH(2) = 2-mercapto-N-quinolin-8-yl-benzamide), another ligand with extended conjugation, affords the Fe(III) complex (Et4N)[Fe(AqPePS)(2)] (1) without any synthetic complication. It is therefore evident that ligands in which the carboxamide and thiolate functionalities are kept in conjugation could be used to isolate Fe(III) complexes with carboxamido-N and thiolato-S coordination. This finding will be very helpful in future research work in the area of modeling the active site of Fe-containing nitrile hydratase.