1-benzyl-4-methyl-4H-1,2,4-triazol-1-ium iodide | 120317-72-8

• 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: 1-benzyl-4-methyl-4H-1,2,4-triazol-1-ium iodide
• 英文别名: 1-benzyl-4-methyl-1,2,4-triazol-4-ium;iodide
• CAS: 120317-72-8
• 化学式: C₁₀H₁₂N₃*I
• 分子量: 301.13
• InChiKey: LKLPPEHWBTWXFR-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.24
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  21.7
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-benzyl-4-methyl-4H-1,2,4-triazol-1-ium iodide 、 nickel dichloride 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以75%的产率得到bis(2-benzyl-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-ylidene)diiodonickel(II)
  参考文献：
  名称：

  Facile Hydrolysis of Nickel(II) Complexes with N-Heterocyclic Carbene Ligands

  摘要：

  Metal complexes with N-heterocyclic carbene ligands (NHC) are ubiquitously used in catalysis, where the stability of the metal-ligand framework is a key issue. Our study shows that Ni-NHC complexes may undergo facile decomposition due to the presence of water in organic solvents (hydrolysis). The ability to hydrolyze Ni(NHC)(2)X-2 complexes decreases in the order of NHC = 1,2,4-triazolium > benzimidazolium approximate to imidazolium. Depending on the ligand and substituents, the half reaction time of the complex decomposition may change from several minutes to hours. The nature of the halogen is also an important factor, and the ability for decomposition of the studied complexes decreases in the order of Cl > Br > I. NMR and MS monitoring revealed that Ni-NHC complexes in the presence of water undergo hydrolysis with Ni-C-carbene bond cleavage, affording the corresponding N,N'-dialkylated azolium salts and nickel(II) hydroxide. These findings are of great importance for designing efficient and recyclable catalytic systems, because trace water is a common contaminant in routine synthetic applications.

  DOI：

  10.1021/acs.organomet.5b00856
• 作为产物：
  描述：

  bis(2-benzyl-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-ylidene)diiodonickel(II) 在 水 作用下， 以 乙腈 为溶剂， 反应 10.0h， 以88%的产率得到1-benzyl-4-methyl-4H-1,2,4-triazol-1-ium iodide
  参考文献：
  名称：

  Facile Hydrolysis of Nickel(II) Complexes with N-Heterocyclic Carbene Ligands

  摘要：

  Metal complexes with N-heterocyclic carbene ligands (NHC) are ubiquitously used in catalysis, where the stability of the metal-ligand framework is a key issue. Our study shows that Ni-NHC complexes may undergo facile decomposition due to the presence of water in organic solvents (hydrolysis). The ability to hydrolyze Ni(NHC)(2)X-2 complexes decreases in the order of NHC = 1,2,4-triazolium > benzimidazolium approximate to imidazolium. Depending on the ligand and substituents, the half reaction time of the complex decomposition may change from several minutes to hours. The nature of the halogen is also an important factor, and the ability for decomposition of the studied complexes decreases in the order of Cl > Br > I. NMR and MS monitoring revealed that Ni-NHC complexes in the presence of water undergo hydrolysis with Ni-C-carbene bond cleavage, affording the corresponding N,N'-dialkylated azolium salts and nickel(II) hydroxide. These findings are of great importance for designing efficient and recyclable catalytic systems, because trace water is a common contaminant in routine synthetic applications.

  DOI：

  10.1021/acs.organomet.5b00856

文献信息

• Becker, H. G. O.; Hoffmann, Gerda; Gwan, Kim Mun, Journal fur praktische Chemie (Leipzig 1954), 1988, vol. 330, # 3, p. 325 - 337
  作者：Becker, H. G. O.、Hoffmann, Gerda、Gwan, Kim Mun、Knuepfer, L.

  DOI：——

  日期：——
• BECKER, H. G. O.;HOFFMANN, GERDA;GWAN, KIM MUN;KNUPFER, L., J. PRAKT. CHEM., 330,(1988) N 3, C. 325-337
  作者：BECKER, H. G. O.、HOFFMANN, GERDA、GWAN, KIM MUN、KNUPFER, L.

  DOI：——

  日期：——