N-p-tolyl-2-oxo-1-naphthylideneamine | 77761-41-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-p-tolyl-2-oxo-1-naphthylideneamine
• 英文别名: 1-[(4-methylanilino)methylidene]naphthalen-2-one
• CAS: 77761-41-2
• 化学式: C₁₈H₁₅NO
• 分子量: 261.323
• InChiKey: DJWBZYCAMXUHHR-UHFFFAOYSA-N

物化性质

• 熔点：
  131 °C
• 沸点：
  467.3±45.0 °C(Predicted)
• 密度：
  1.263±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-p-tolyl-2-oxo-1-naphthylideneamine 、 zinc(II) chloride 以 乙醇 为溶剂， 以90%的产率得到dichloro-bis(N-p-tolyl-2-oxo-1-naphthylideneamine-O)zinc(II)
  参考文献：
  名称：

  Complexes of zinc(II) halides with N-benzyl- and N-p-tolyl-2-oxo-1-naphthylideneamine – preparation and characterization

  摘要：

  A series of novel complexes, dihalo-bis(N-benzyl-2-oxo-1-naphthylideneamine-O)zinc(II), ZnX2(bznapH)(2) (1-3), dihalo-bis(N-p-tolyl-2-oxo-1-naphthylideneamine-O)zinc(II), ZnX2(tolnapH)(2) (4-6), of the general formula [ZnX2(LH)(2)] X = Cl, Br, I, have been prepared. The crystal structures of four compounds (1-4) reveal four coordinated zinc centres by two halogen and two oxygen atoms from the Schiff-base in the form of distorted tetrahedra. Complex 4 crystallizes as the one-to-one solvate with ethanol.The tetrahedral distortion is most pronounced in the structure of ZnI2(bznapH)(2) complex. X-ray structural data showed that the Schiff-base ligand in the naphthylideneamine tautomeric form is weakly bound to Zn atom in 1-4 (being in the range from 1.952(3) Angstrom in 2 to 2.002(3) Angstrom in 4). The molecular structures of 1-4 are governed by the type of halide and the corresponding Schiff-base. Although the structure comparison of ZnX2(bznapH)(2) vs. ZnX2(tolnapH)(2) leads to the conclusion that ligand spatial accomodation (non-planar bznapH with aliphatic interruption vs. aromatic: tolnapH) is the dominating factor in the crystal structures. The crystal structures of 2-4 are dominated by van der Waals forces. There is a weak intermolecular hydrogen bond of the C-(HCl)-Cl-... type in 1 (3.710(5) Angstrom joining molecules into endless chains. The UV-Vis and H-1 NMR spectra, obtained in ethanolic and acetone solution indicate that the complexes do not exist in the solutions. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2003.12.023

文献信息

• Preparation and characterization of the 1:1 adducts of mercury(II) halides with N-benzyl- and N-p-tolyl-2-oxo-1-naphthylideneamine. The crystal and molecular structures of two isostructural di-μ-halo-bis[halo(N-benzyl-2-oxo-1-naphthylideneamine)mercury(II)] adducts (halo=chloro, bromo)
  作者：Zora Popović、Vibor Roje、Gordana Pavlović、Dubravka Matković-Čalogović、Maša Rajić、Gerald Giester

  DOI：10.1016/s0020-1693(01)00542-4

  日期：2001.10

  series of adducts of the type HgX2(C18H15NO) [X=Cl−, Br−, I−; C18H15NO=N-benzyl-2-oxo-1-naphthylideneamine (bznapH), N-p-tolyl-2-oxo-1-naphthylideneamine (tolnapH)] was obtained by refluxing the solution of the corresponding mercury(II) salt and the related naphthylideneamine in absolute ethanol in a 1:1 molar ratio. The adducts di-μ-chloro-bis[chloro(N-benzyl-2-oxo-1-naphthylideneamine)mercury(II)], HgCl2(bznapH)

  一系列HGX的类型的加合物的2（C 18 H ^ 15 NO）[X =氯- ，溴- ，我- ; Ç 18 ħ 15 NO = ñ -苄基-2-氧代-1- naphthylideneamine（bznapH），ñ - p -甲苯基-2-氧代-1- naphthylideneamine（tolnapH）]通过回流对应的汞的溶液（II获得）盐和相关的萘亚胺在无水乙醇中的摩尔比为1：1。二-氯-双-[氯（N-苄基-2-氧代-1-萘亚胺）汞（II），HgCl 2（bznapH）（1）和二-溴-双[溴（N-（苄基-2-氧代-1-萘基亚胺）汞（II）]，HgBr 2（bznapH）（2）是同构的，汞的有效配比为2 + 2。所述HGX 2部分被保持在加合物和含有两个共价连接的氯[2.321（3）和在2.299（3）1 [在2.446（1）和2.422（1）]或溴原子的2 ]。这些部分通过桥接卤素原子的额外接触相互连接[分别在1和2中的Hg
• Complexes of zinc(II) halides with N-benzyl- and N-p-tolyl-2-oxo-1-naphthylideneamine – preparation and characterization
  作者：Zora Popović、Vibor Roje、Gordana Pavlović、Dubravka Matković-Čalogović、Maša Rajić、Ivan Leban

  DOI：10.1016/j.poly.2003.12.023

  日期：2004.5

  A series of novel complexes, dihalo-bis(N-benzyl-2-oxo-1-naphthylideneamine-O)zinc(II), ZnX2(bznapH)(2) (1-3), dihalo-bis(N-p-tolyl-2-oxo-1-naphthylideneamine-O)zinc(II), ZnX2(tolnapH)(2) (4-6), of the general formula [ZnX2(LH)(2)] X = Cl, Br, I, have been prepared. The crystal structures of four compounds (1-4) reveal four coordinated zinc centres by two halogen and two oxygen atoms from the Schiff-base in the form of distorted tetrahedra. Complex 4 crystallizes as the one-to-one solvate with ethanol.The tetrahedral distortion is most pronounced in the structure of ZnI2(bznapH)(2) complex. X-ray structural data showed that the Schiff-base ligand in the naphthylideneamine tautomeric form is weakly bound to Zn atom in 1-4 (being in the range from 1.952(3) Angstrom in 2 to 2.002(3) Angstrom in 4). The molecular structures of 1-4 are governed by the type of halide and the corresponding Schiff-base. Although the structure comparison of ZnX2(bznapH)(2) vs. ZnX2(tolnapH)(2) leads to the conclusion that ligand spatial accomodation (non-planar bznapH with aliphatic interruption vs. aromatic: tolnapH) is the dominating factor in the crystal structures. The crystal structures of 2-4 are dominated by van der Waals forces. There is a weak intermolecular hydrogen bond of the C-(HCl)-Cl-... type in 1 (3.710(5) Angstrom joining molecules into endless chains. The UV-Vis and H-1 NMR spectra, obtained in ethanolic and acetone solution indicate that the complexes do not exist in the solutions. (C) 2004 Elsevier Ltd. All rights reserved.