N4-(N,N-diphenylamino)-1,2,4-triazole | 873590-08-0

• 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: N4-(N,N-diphenylamino)-1,2,4-triazole
• 英文别名: N,N-diphenyl-1,2,4-triazol-4-amine
• CAS: 873590-08-0
• 化学式: C₁₄H₁₂N₄
• 分子量: 236.276
• InChiKey: JXOLKKPXNODQSH-UHFFFAOYSA-N

物化性质

• 沸点：
  401.0±28.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N4-(N,N-diphenylamino)-1,2,4-triazole 在 氯化亚砜 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 生成 N4-(N,N-diphenylamino)-3,5-bis-(chloromethyl)-1,2,4-triazole
  参考文献：
  名称：

  Effect of N⁴-Substituent Choice on Spin Crossover in Dinuclear Iron(II) Complexes of Bis-Terdentate 1,2,4-Triazole-Based Ligands

  摘要：

  Seven new dinuclear iron(II) complexes of the general formula [Fe-2(II)(PMKT)(2)] (BF4)(4)center dot solvent, where PMRT is a 4-substituted-3,5-bis{[(2-pyridylmethyl)-amino]methyl}-4H-1,2,4-triazole, have been prepared in order to investigate the substituent effect on the spin crossover event. Variable temperature magnetic susceptibility and Fe-57 Mossbauer spectroscopy studies show that two of the complexes, [Fe-2(II)(PMPT)(2)](BF4)(4)center dot H2O (N-4 substituent is pyrrolyl) and [Fe-2(II)(PM(Ph)AT)(2)](BF4)(4) (N-4 is N,N-diphenylamine), are stabilized in the [HS-HS] state between 300 and 2 K with weak antiferromagnetic interactions between the iron(II) centers. Five of the complexes showed gradual half spin crossover, from [HS-HS] to [HS-LS], with the following, T-1/2 (K) values: 234 for [Fe-2(II)(PMibT)(2)](BF4)(4)center dot 3H(2)O (N-4 is isobutyl), 147 for [Fe-2(II)(PMBzT)(2)](BF4)(4) (N-4 is benzyl), 133 for [Fe-2(II)((PMPhT)-Ph-CF3)(2)](BF4)(4)center dot DMF center dot H2O (N-4 is 3,5-bis(trifluoromethyl)phenyl), 187 for [Fe-2(II)(PMPhT)(2)](BF4)(4) (N-4 is phenyl), and 224 for [Fe-2(II)(PMC16T)(2)](BF4)(4) (N-4 is hexadecyl). Structure, determinations carried out for three complexes, [Fe-2(II)(PMPT)2](BF4)(4)center dot 4DMF, [Fe-2(II)(PMBzT)(2)](BF4)(4)center dot CH3CN, and [Fe-2(II)(PM(Ph)AT)(2)](BF4)(4)center dot solvent, revealed that in all three complexes both iron(II) centers are stabilized in the high spin state at 90 K. A general and reliable 4-step route to PMRT ligands is also detailed.

  DOI：

  10.1021/ic4014416
• 作为产物：
  描述：

  1,1-二苯肼盐酸盐 、 N,N-dimethylformamide azine dihydrochloride 以 吡啶 为溶剂， 以61%的产率得到N4-(N,N-diphenylamino)-1,2,4-triazole
  参考文献：
  名称：

  Effect of N⁴-Substituent Choice on Spin Crossover in Dinuclear Iron(II) Complexes of Bis-Terdentate 1,2,4-Triazole-Based Ligands

  摘要：

  Seven new dinuclear iron(II) complexes of the general formula [Fe-2(II)(PMKT)(2)] (BF4)(4)center dot solvent, where PMRT is a 4-substituted-3,5-bis{[(2-pyridylmethyl)-amino]methyl}-4H-1,2,4-triazole, have been prepared in order to investigate the substituent effect on the spin crossover event. Variable temperature magnetic susceptibility and Fe-57 Mossbauer spectroscopy studies show that two of the complexes, [Fe-2(II)(PMPT)(2)](BF4)(4)center dot H2O (N-4 substituent is pyrrolyl) and [Fe-2(II)(PM(Ph)AT)(2)](BF4)(4) (N-4 is N,N-diphenylamine), are stabilized in the [HS-HS] state between 300 and 2 K with weak antiferromagnetic interactions between the iron(II) centers. Five of the complexes showed gradual half spin crossover, from [HS-HS] to [HS-LS], with the following, T-1/2 (K) values: 234 for [Fe-2(II)(PMibT)(2)](BF4)(4)center dot 3H(2)O (N-4 is isobutyl), 147 for [Fe-2(II)(PMBzT)(2)](BF4)(4) (N-4 is benzyl), 133 for [Fe-2(II)((PMPhT)-Ph-CF3)(2)](BF4)(4)center dot DMF center dot H2O (N-4 is 3,5-bis(trifluoromethyl)phenyl), 187 for [Fe-2(II)(PMPhT)(2)](BF4)(4) (N-4 is phenyl), and 224 for [Fe-2(II)(PMC16T)(2)](BF4)(4) (N-4 is hexadecyl). Structure, determinations carried out for three complexes, [Fe-2(II)(PMPT)2](BF4)(4)center dot 4DMF, [Fe-2(II)(PMBzT)(2)](BF4)(4)center dot CH3CN, and [Fe-2(II)(PM(Ph)AT)(2)](BF4)(4)center dot solvent, revealed that in all three complexes both iron(II) centers are stabilized in the high spin state at 90 K. A general and reliable 4-step route to PMRT ligands is also detailed.

  DOI：

  10.1021/ic4014416

文献信息

• Synthesis, structure and electronic properties of N-dialkylamino- and N-alkoxy-1,2,4-triazol-3-ylidene ligands
  作者：Manuel Alcarazo、Rosario Fernández、Eleuterio Álvarez、José M. Lassaletta

  DOI：10.1016/j.jorganchem.2005.07.120

  日期：2005.12

  4-Amino- and 4-alkoxy-1,2,4-triazoles 4a-d and 6 were readily obtained from the reaction of N,N-dimethyiformamidazin dihydrochloride 3 with hydrazines 2 and hydroxylamine 5. Alkylation of compounds 4a-d and 6 by MeOTf or MeI afforded azolium salts 9-11, which in turn were transformed into Rh(l) carbene complexes 13-15, Ag carbenes 16, and cationic Rh(l) bis-carbenes 17. Additionally.. complexes 13 and 15 were transformed into dicarbonyl derivatives 18 and 19, and the carbonyl stretching frequencies of these compounds were used to evaluate the effect of the amino and alkoxy groups in the sigma-donor ability of these 1,2,4-triazol-3-ylidenes. (c) 2005 Elsevier B.V. All rights reserved.