1-benzyl-4-phenyl-1,2,4-triazolium chloride | 120337-45-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-benzyl-4-phenyl-1,2,4-triazolium chloride
• 英文别名: 1-Benzyl-4-phenyl-1,2,4-triazol-4-ium;chloride
• CAS: 120337-45-3
• 化学式: C₁₅H₁₄N₃*Cl
• 分子量: 271.749
• InChiKey: ZCZVXKQMVMMIBB-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.79
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzyl-4-phenyl-1,2,4-triazolium chloride 在 甲醇 、 Na₂CO₃-HCl buffer 、 水 作用下， 生成 Formamide, N-phenyl-N-[[(phenylmethyl)hydrazono]methyl]-
  参考文献：
  名称：

  Kinetics and mechanism of ring cleavage of 1-Benzyl-4-phenyl-1,2,4-triazolium Chloride

  摘要：

  1-Benzyl-4-phenyl-1,2,4-triazolium chloride (1) is cleaved by aqueous sodium hydroxide to form 4-benzyl-1-formyl-1-phenyl-amidrazone (5), the structure of which is proved by mass spectroscopy. The kinetics of the cleavage reaction are studied by UV spectroscopy in methanol/water 1:1 (v/v) in the presence of Na2CO3/HCl buffer at pH values from 11.64 to 12.61. The reaction obeys a first-order kinetic law. The rate constants do not depend linearly on the hydroxide concentration. This is in coincidence with fast formation of the pseudobase from 1, followed by fast deprotonation to the pseudobase anion, and slow decay to the amidrazone. The pseudobase anion is proved spectroscopically, and its spectroscopically determined pK(QOH) = 12.7 coincides with that from the kinetic experiments. The equilibrium constant of pseudobase formation pK(A) = 10.99 is two orders of magnitude higher than that from the azo-coupling of 1 [1] which shows that in the azocoupling not the pseudobase but its methyl ether (pK(QOMe) = 8.7) is active.4-Benzyl-1-formyl-1-phenyl-amidrazone (5) re-cyclizes in the presence of HCl in MeOH/H2O to form 1. The kinetics of this reaction are also studied.

  DOI：

  10.1002/prac.19923340306
• 作为产物：
  描述：

  1-Benzyl-5-methoxy-4-phenyl-4,5-dihydro-1H-[1,2,4]triazole 以 水 为溶剂， 生成 甲醇 、 1-benzyl-4-phenyl-1,2,4-triazolium chloride
  参考文献：
  名称：

  Kinetics and mechanism of ring cleavage of 1-Benzyl-4-phenyl-1,2,4-triazolium Chloride

  摘要：

  1-Benzyl-4-phenyl-1,2,4-triazolium chloride (1) is cleaved by aqueous sodium hydroxide to form 4-benzyl-1-formyl-1-phenyl-amidrazone (5), the structure of which is proved by mass spectroscopy. The kinetics of the cleavage reaction are studied by UV spectroscopy in methanol/water 1:1 (v/v) in the presence of Na2CO3/HCl buffer at pH values from 11.64 to 12.61. The reaction obeys a first-order kinetic law. The rate constants do not depend linearly on the hydroxide concentration. This is in coincidence with fast formation of the pseudobase from 1, followed by fast deprotonation to the pseudobase anion, and slow decay to the amidrazone. The pseudobase anion is proved spectroscopically, and its spectroscopically determined pK(QOH) = 12.7 coincides with that from the kinetic experiments. The equilibrium constant of pseudobase formation pK(A) = 10.99 is two orders of magnitude higher than that from the azo-coupling of 1 [1] which shows that in the azocoupling not the pseudobase but its methyl ether (pK(QOMe) = 8.7) is active.4-Benzyl-1-formyl-1-phenyl-amidrazone (5) re-cyclizes in the presence of HCl in MeOH/H2O to form 1. The kinetics of this reaction are also studied.

  DOI：

  10.1002/prac.19923340306

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：——
• Additionsverbindungen von Triazolium- oder Tetrazoliumsalzen
  申请人：BASF AKTIENGESELLSCHAFT

  公开号：EP0786456B1

  公开（公告）日：1999-05-06
• Kinetics and mechanism of ring cleavage of 1-Benzyl-4-phenyl-1,2,4-triazolium Chloride
  作者：H. G. O. Becker、Kim Mun Gwan

  DOI：10.1002/prac.19923340306

  日期：——

  1-Benzyl-4-phenyl-1,2,4-triazolium chloride (1) is cleaved by aqueous sodium hydroxide to form 4-benzyl-1-formyl-1-phenyl-amidrazone (5), the structure of which is proved by mass spectroscopy. The kinetics of the cleavage reaction are studied by UV spectroscopy in methanol/water 1:1 (v/v) in the presence of Na2CO3/HCl buffer at pH values from 11.64 to 12.61. The reaction obeys a first-order kinetic law. The rate constants do not depend linearly on the hydroxide concentration. This is in coincidence with fast formation of the pseudobase from 1, followed by fast deprotonation to the pseudobase anion, and slow decay to the amidrazone. The pseudobase anion is proved spectroscopically, and its spectroscopically determined pK(QOH) = 12.7 coincides with that from the kinetic experiments. The equilibrium constant of pseudobase formation pK(A) = 10.99 is two orders of magnitude higher than that from the azo-coupling of 1 [1] which shows that in the azocoupling not the pseudobase but its methyl ether (pK(QOMe) = 8.7) is active.4-Benzyl-1-formyl-1-phenyl-amidrazone (5) re-cyclizes in the presence of HCl in MeOH/H2O to form 1. The kinetics of this reaction are also studied.