1-[N-(2-pyridyl)aminomethylidene]-2(1H)-naphthalenone

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-[N-(2-pyridyl)aminomethylidene]-2(1H)-naphthalenone
• 英文别名: (1Z)-1-[(pyridin-2-ylamino)methylidene]naphthalen-2-one
• 化学式: C₁₆H₁₂N₂O
• 分子量: 248.284
• InChiKey: TUSHAFQDZDKGGP-KAMYIIQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氨基吡啶 、 2-羟基-1-萘甲醛 以 甲醇 为溶剂， 反应 0.5h， 以95%的产率得到1-[N-(2-pyridyl)aminomethylidene]-2(1H)-naphthalenone
  参考文献：
  名称：

  Intramolecular hydrogen bonding and tautomerism in Schiff bases. Part II. Structures of 1-[ N -(2-pyridyl)aminomethylidene}-2(1H)-naphtalenone (1) and bis[2-hydroxy-κ O – N -(2-pyridyl)-1-naphthaldiminato-κ N ]zinc(II) (2)

  摘要：

  The Schiff base ligand (1) and its Zn(II) complex (2) have been synthesized and their crystal structures have been determined. Compound (1) crystallizes in the monoclinic space group C2/c with a = 26.993(2), b = 5.891(1), c = 16.000(2) W, P = 103.29(1)degrees, V = 2476.0(6) Angstrom(3), Z = 8 and D-x = 1.332 g cm(-3) Compound (2) crystallizes in the orthorhombic space group Pbca with a = 19.580(3), b = 9.416(2), c = 27.801(2) Angstrom, V = 5125.5(6) Angstrom(3), Z = 8 and D-x = 1.451g cm(-3) In the crystal structure of the free Schiff base ligand (1), the existence of a strong intramolecular N-H...O hydrogen bond INO = 2.572(4), N-H = 0.90(4), H...O = 1.759(4) Angstrom, N-H...O = 149.6(3)degrees] is observed. The C-N amine bond and C-N-C bond angle are 1.345(4)Angstrom and 124.4(3)degrees, respectively. The C3 = O1 and C4 = C5 bond lengths [1.274(4) and 1.351(5) Angstrom] are shortened by the pronounced quinoidal effect. In solution, compound (1) is in tautomeric equilibria (phenol-imine, O-H ... N keto-amine, O ... H-N forms), as supported by H-1 NMR and UV-visible data. In the crystal structure of the Zn(II) complex (2), zinc atom has a distorted tetrahedral coordination. One of the pyridine N atom of the ligands is in close contact with the Zn(II) atom [Zn1 ... N4 = 2.864(5) Angstrom].It is interesting that the C-N amine bond [1.345(4) Angstrom] in compound (1) changes to the imine bond [1.27(5) Angstrom] in the Zn(TI) complex (2). (C) 2000 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-2860(99)00376-2

文献信息

• Syntheis of Novel Anil-Like Compounds from Heteroaryl Amines, Naphthols, and Triethylorthoformate Under Solvent-Free Conditions
  作者：Abolfazl Olyaei、Fatemeh Gesmati、Mahdieh Sadeghpour、Bahareh Shams、Maryam Alizadeh

  DOI：10.1080/00397911.2010.542860

  日期：2012.6

  under solvent-free conditions lead to the formation of the corresponding new hydroxynaphthalidene heteroaryl amines (anil-like) in moderate to good yields in an environmentally friendly reaction in organic synthesis. Investigation of 1H NMR and infrared spectra indicated that the compounds are in tautomeric equilibrium between the enol-imine and keto-enamine forms. Furthermore, intramolecular hydrogen

  摘要 萘酚、原甲酸三乙酯和杂芳胺在无溶剂条件下在甲酸催化剂存在下的一锅三组分反应导致形成相应的新型羟基萘杂芳胺（类苯胺），收率中等至良好。在有机合成中的环境友好反应中。1H NMR 和红外光谱的研究表明，这些化合物在烯醇-亚胺和酮-烯胺形式之间处于互变异构平衡。此外，在合成的席夫碱中观察到分子内氢键。图形概要
• Intramolecular hydrogen bonding and tautomerism in Schiff bases. Part II. Structures of 1-[ N -(2-pyridyl)aminomethylidene}-2(1H)-naphtalenone (1) and bis[2-hydroxy-κ O – N -(2-pyridyl)-1-naphthaldiminato-κ N ]zinc(II) (2)
  作者：T. Hökelek、Z. Kılıc、M. Isıklan、M. Toy

  DOI：10.1016/s0022-2860(99)00376-2

  日期：2000.5

  The Schiff base ligand (1) and its Zn(II) complex (2) have been synthesized and their crystal structures have been determined. Compound (1) crystallizes in the monoclinic space group C2/c with a = 26.993(2), b = 5.891(1), c = 16.000(2) W, P = 103.29(1)degrees, V = 2476.0(6) Angstrom(3), Z = 8 and D-x = 1.332 g cm(-3) Compound (2) crystallizes in the orthorhombic space group Pbca with a = 19.580(3), b = 9.416(2), c = 27.801(2) Angstrom, V = 5125.5(6) Angstrom(3), Z = 8 and D-x = 1.451g cm(-3) In the crystal structure of the free Schiff base ligand (1), the existence of a strong intramolecular N-H...O hydrogen bond INO = 2.572(4), N-H = 0.90(4), H...O = 1.759(4) Angstrom, N-H...O = 149.6(3)degrees] is observed. The C-N amine bond and C-N-C bond angle are 1.345(4)Angstrom and 124.4(3)degrees, respectively. The C3 = O1 and C4 = C5 bond lengths [1.274(4) and 1.351(5) Angstrom] are shortened by the pronounced quinoidal effect. In solution, compound (1) is in tautomeric equilibria (phenol-imine, O-H ... N keto-amine, O ... H-N forms), as supported by H-1 NMR and UV-visible data. In the crystal structure of the Zn(II) complex (2), zinc atom has a distorted tetrahedral coordination. One of the pyridine N atom of the ligands is in close contact with the Zn(II) atom [Zn1 ... N4 = 2.864(5) Angstrom].It is interesting that the C-N amine bond [1.345(4) Angstrom] in compound (1) changes to the imine bond [1.27(5) Angstrom] in the Zn(TI) complex (2). (C) 2000 Elsevier Science B.V. All rights reserved.