bis(2-(4'-aminophthalimidomethyl)pyridine)copper(I) perchlorate | 795297-16-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: bis(2-(4'-aminophthalimidomethyl)pyridine)copper(I) perchlorate
• 英文别名: [copper(I) (2-(4'-aminophthalimidomethyl)pyridine)2] perchlorate；5-Amino-2-(pyridin-2-ylmethyl)isoindole-1,3-dione;copper(1+);perchlorate
• CAS: 795297-16-4
• 化学式: C₂₈H₂₂CuN₆O₄*ClO₄
• 分子量: 669.517
• InChiKey: LQSHRUIYEZZAMJ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.84
• 重原子数：
  44
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  227
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  copper(II) perchlorate hexahydrate 、 2-(4'-aminophthalimidomethyl)pyridine 以 甲醇 为溶剂， 以25%的产率得到bis(2-(4'-aminophthalimidomethyl)pyridine)copper(I) perchlorate
  参考文献：
  名称：

  In Situ Reduction of Copper(II) Forming an Unusually Air Stable Linear Complex of Copper(I) with a Fluorescent Tag

  摘要：

  A new fluorescent ligand (phi(f) = 0.8 in dioxane), 2-(4'-aminophthalimidomethyl)pyridine (L), has been synthesized. A one-pot synthesis of its copper(I) complex upon reduction of copper(II) is achieved at room temperature. This complex, which has been characterized by X-ray crystallography, shows a linear N-Cu-N geometry with Cu-N bond lengths of 1.89 Angstrom. X-ray structure reveals weak (CuO)-O-... interactions between copper and one of the imide oxygen atoms of the ligand framework. Additional weak (CuO)-O-... interactions between copper and oxygen atoms of the CIO4- counteranion are detected that lead to a zigzag polymeric chain with alternate CIO4- and copper ions. A 2-D intermolecular hydrogen bonding network is also observed. This complex is found to be highly inert toward oxidation both in the solid state and in solution.

  DOI：

  10.1021/ic0490019

文献信息

• Synthesis and structure of unusually stable linear copper(I) complexes with blue fluorescence
  作者：Sandip Banthia、Anunay Samanta

  DOI：10.1016/j.poly.2006.01.025

  日期：2006.7

  A new fluorescent ligand 2-(4-aminophthalimidoethyl)pyridine (L-2) has been synthesized. Solid state structures of L-2 and 2-(4'-aminophthalimidomethyl)pyridine (L-1) have been determined by X-ray crystallography. While L-1 crystallizes in the non-centrosymmetric orthorhombic space group Fdd2, L-2 crystallizes in the monoclinic space group C2/c. The molecular packing in both systems is dominated by intermolecular N-H center dot center dot center dot O and N-H center dot center dot center dot N hydrogen bonds and relative bending of the planes defined by the pyridine and phthalimide moieties. An unusually stable two-coordinate complex of copper(I) with L-2, Cu(L-2)(2), has been synthesized upon in situ reduction of copper(II) at room temperature. This complex, which has been characterized by X-ray crystallography, crystallizes in the centrosymmetric space group C2/c with a linear N-Cu-N geometry. The Cu-N bond distance (1.89 angstrom) in Cu(L-2)(2) is found to be similar to that in Cu(L-1)(2). Both the complexes display interesting structural feature, arising from weak Cu center dot center dot center dot O interactions (3.12 angstrom in Cu(L-1)(2) and 2.71 angstrom in Cu(L-2)(2)) between the copper and oxygen atoms of the ClO4- counteranion, leading to a linear network with alternate ClO4- and Cu+ ions. A 2-D network determined by intermolecular N-H center dot center dot center dot O hydrogen bonding is also observed. These complexes are found to be highly resistant toward oxidation both in the solid state and in solution. The new complex Cu(L-2)(2), in which the metal center is more separated from the 4-aminophthalimide moieties, exhibits lesser stability than Cu(L-1)(2). Close contact between copper and one of the imide oxygen atoms of the ligand framework was detected as 3.03 angstrom in Cu(L-1)(2) and 4.0 angstrom in Cu(L-2)(2), indicating a relatively weaker electronic interaction in the later complex. Thus, the exceptional stability of these complexes is attributed to the electronic environment provided by the 4-aminophthalimide and perchlorate moieties on the metal center. (C) 2006 Elsevier Ltd. All rights reserved.