N-{(2-pyridyl)methyliden}-6-coumarin

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: N-{(2-pyridyl)methyliden}-6-coumarin
• 英文别名: 6-(Pyridin-2-ylmethylideneamino)chromen-2-one；6-(pyridin-2-ylmethylideneamino)chromen-2-one
• 化学式: C₁₅H₁₀N₂O₂
• 分子量: 250.257
• InChiKey: IEOYSRFWLNACPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 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：
  51.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-{(2-pyridyl)methyliden}-6-coumarin 在 silver nitrate 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 14.0h， 生成 Pt(N-{(2-pyridyl)methyliden}-6-coumarin)₂
  参考文献：
  名称：

  Palladium(II) and platinum(II) complexes of N-{(2-pyridyl)methyliden}-6-coumarin and N-{(2-hydroxy)benzyliden}-6-coumarin

  摘要：

  N-{(2-pyridyl) methyliden}-6-coumarin (N,N' chelator; N,N' refer to N(pyridyl) and N(imine), respectively) and N-{(2-hydroxy) benzyliden}-6-coumarin (N, O chelator; N, O refer to N(pyridyl) and O(phenolato)) have been used to synthesize palladium(II) and platinum(II) complexes - [ M(N,N')Cl-2], [M(N,O)(2)], [M(N,N')(2)](ClO4)(2) and [M(N,N')(N,O)]ClO4 (M = Pd, Pt). These complexes have been characterized by spectroscopic techniques (FTIR, UV-Vis, Mass, NMR) and the structural confirmation has been achieved in case of two representative complexes, [Pd(N,N')Cl-2] and [Pd(N,O)(2)] by the single crystal X-ray diffraction studies. The complexes emit at 409-557 nm and life times are in the range 0.52-1.98 ns. The cyclic voltammetric data of the complexes show the reduction of chelated ligand. The electronic configuration of the complexes is assessed by DFT computation and the spectral and redox properties are explained by TD-DFT calculation. (C) 2014 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2014.07.014
• 作为产物：
  描述：

  6-硝基香豆素 在 铁粉 、 氯化铵 作用下， 生成 N-{(2-pyridyl)methyliden}-6-coumarin
  参考文献：
  名称：

  铜（I）/银（I）-膦-N -{（2-吡啶基）甲基} -6-香豆素配合物：合成，结构，氧化还原互转换，光物理性质和DFT计算

  摘要：

  Cu（I）和Ag（I）与双（二苯基膦基）甲烷（dppm）/ 1,2-双（二苯基膦基）乙烷（dppe）和N -{（2-吡啶基）亚甲基} -6-香豆素的混合配体配合物（L）已通过元素分析，电导率，1 H NMR，UV-Vis和荧光光谱数据进行了合成和表征。dppm与M（I）的配位形成双核金属环[[L] M（μ-dppm）2 M（L）]（X）2（X = NO 3或ClO 4），其中一种配合物具有通过单晶X射线结构分析来表征。dppe配体是双齿螯合剂，由[Cu（dppe）（L）] ClO 4的X射线结构支撑。在AG（I）络合物，DPPE被用作桥键形成剂，以形成双核配合物[（L）的Ag（μ-DPPE）的Ag（L）]（NO 3）2，和NO 3 -不对称螯合银（I ），表现出与溶剂极性有关的配位关系。在配位极性溶剂（如MeCN）中，硝酸根基团解离并显示出电导率，而在硝基苯中，络合物不导电且不支持解离。配

  DOI：

  10.1016/j.poly.2012.11.050

文献信息

• Cobalt(II), nickel(II) and copper(II) complexes of N-{(2-pyridyl)methyliden}-6-coumarin: Characterization, DNA interaction, catecholase activity and theoretical interpretation
  作者：Suman Roy、Shyamal Kumar Sarkar、Rajat Saha、Tapan Kumar Mondal、Chittaranjan Sinha

  DOI：10.1016/j.ica.2018.05.001

  日期：2018.10

  pyridyl-N (N) and imine-N (N/) the structure of [Ni(N3)2(N,N/)2] follows cis-cis-cis-(ccc)-Ni(N3)2(N,N/)2] configuration. The complexes are paramagnetic and the EPR spectra of Cu(II) complexes provide information about hyperfine and super-hyperfine structures. The cyclic voltammogram shows M(II)/M(III), Cu(I)/Cu(II) and reductions of chelated diimine ligand. Only [Cu(N3)2(N,N/)2] (3) shows efficient catecholase

  摘要[M（X）2（N，N /）2]（M = Co（II），Ni（II），Cu（II）; X = N3-，SCN-; N，N / = N-（ 2-吡啶基亚甲基} -6-香豆素，二齿二亚胺吡啶基-N（N），亚胺-N（N /）螯合剂）已通过不同的理化数据进行了表征。通过单晶X射线衍射数据已经对[Ni（N3）2（N，N /）2]进行了结构确认。考虑叠氮化物-N（N3-），吡啶基-N（N）和亚胺-N（N /）的配位顺序，[Ni（N3）2（N，N /）2]的结构为顺-顺-顺式（ccc）-Ni（N3）2（N，N /）2]配置。配合物是顺磁性的，Cu（II）配合物的EPR谱提供了有关超细和超超细结构的信息。循环伏安图显示M（II）/ M（III），Cu（I）/ Cu（II）和螯合的二亚胺配体的还原。只有[Cu（N3）2（N，N /）2]（3）表现出有效的儿茶酚酶活性（比率为4。93×10−4 min-1），而[Cu（SCN）2（N，N
• Synthesis, structure, spectroscopic properties, electrochemistry, and DFT correlative studies of N-[(2-pyridyl)methyliden]-6-coumarin complexes of Cu(I) and Ag(I)
  作者：Suman Roy、Tapan Kumar Mondal、Partha Mitra、Elena Lopez Torres、Chittaranjan Sinha

  DOI：10.1016/j.poly.2010.12.037

  日期：2011.4

  reacts with [Cu(MeCN)4]ClO4/AgNO3 to synthesize Cu(I) and Ag(I) complexes of formulae, [Cu(L)2]ClO4 and [Ag(L)2]NO3, respectively. While similar reaction in the presence of PPh3 has isolated [Cu(L)(PPh3)2]ClO4 and [Ag(L)(PPh3)2]NO3. All these compounds are characterized by FTIR, UV–Vis and 1H NMR spectroscopic data. In case of [Cu(L)(PPh3)2]ClO4 and [Ag(L)(PPh3)2]NO3, the structures have been confirmed

  6-氨基香豆素与吡啶-2-甲醛反应，合成了N-[（2-吡啶基）亚甲基] -6-香豆素（L）。配体L与[Cu（MeCN）4 ] ClO 4 / AgNO 3反应以合成具有式[Cu（L）2 ] ClO 4和[Ag（L）2的Cu（I）和Ag（I）配合物] NO 3。尽管在PPh 3存在下进行了类似的反应，但分离出了[Cu（L）（PPh 3）2 ] ClO 4和[Ag（L）（PPh 3）2 ] NO 3。所有这些化合物的特征均在于FTIR，UV-Vis和11 H NMR光谱数据。在[Cu（L）（PPh 3）2 ] ClO 4和[Ag（L）（PPh 3）2 ] NO 3的情况下，通过X射线晶体学确认了结构。配合物的结构是扭曲的四面体，其中L坐标为N，N'双齿，PPh 3占据了其他两个配位点。配体和配合物是荧光的，[Cu（L）（PPh 3）2 ] ClO 4和[Ag（L）（PPh 3）2 ] NO 3的荧光量子产率高于[Cu（L）2
• Structure, spectra and electrical conductivity of copper(I) and silver(I) phosphino bridging mixed ligand complexes with coumarinyl Schiff base
  作者：Suman Roy、Tapan Kumar Mondal、Animesh Layek、Rajat Saha、Chittaranjan Sinha

  DOI：10.1016/j.ica.2017.08.031

  日期：2018.1

  = Cu(I), Ag(I); L, N-(2-pyridyl)methyliden}-6-coumarin; X = NO 3 - or ClO 4 - ; dppp, 1,3-bis(diphenylphosphino)propane; dppb, 1,4-bis(diphenylphosphino)butane; dpph, 1,6-bis(diphenylphosphino)hexane) have been spectroscopically characterised and one of the complexes, [-Ag(L)(μ-dpph)-] n (NO 3 ) n has been structurally supported by single crystal X-ray diffraction measurement. The current(I)-voltage(V)

  摘要配位聚合物[-M（L）（μ-dppp/ dppb / dpph）-] n（X）n，（M = Cu（I），Ag（I）; L，N-（2-吡啶基）亚甲基} -6-香豆素； X ＝ NO 3-或ClO 4-； dppp，1，3-双（二苯基膦基）丙烷； dppb，1，4-双（二苯基膦基）丁烷； dpph，1，6-双（二苯基膦基） ）已被光谱表征，其中一种配合物[-Ag（L）（μ-dpph）-] n（NO 3）n通过单晶X射线衍射测量得到了结构支撑。配位聚合物的电流（I）-电压（V）特性在半导体范围内（〜10 -3 Sm -1），本质上为非欧姆性。带隙低于3.0 eV。配合物在可见光区域（509 – 522 nm）内发射，固相发射比溶液相发射强度大。循环伏安法显示Cu（II）/ Cu（I）在0.8 – 0.9 V时偶合，配体还原在-0.59至-0之间。
• Structure, fluorescence, redox properties and theoretical interpretation of heteroleptic copper(I) and silver(I) complexes of N-[(2-pyridyl)methyliden]-6-coumarin and triphenylphosphine
  作者：Suman Roy、Pallab Gayen、Rajat Saha、Tapan Kumar Mondal、Chittaranjan Sinha

  DOI：10.1016/j.ica.2013.10.029

  日期：2014.1

  [MX(L)(PPh3)] (L = N-[(2-pyridyl)methyliden]-6-coumarin; M = Cu(I), Ag(I); X = Cl, Br, I, N-3, SCN) are characterized by spectroscopic data. The X-ray structure of [CuCl(L)(PPh3)] shows CuN2PCl distorted tetrahedral coordination (L acts N,N chelator). The complexes show emission and the emission efficiency is dependent on nature of M and X; Cu(I) complexes (d(10)) are more emissive than Ag(I) complexes which may be due to heavy atom effect of silver. [Cu(SCN)(L)(PPh3)] shows highest emission intensity in the series. The cyclic voltammogram of [CuX(L)(PPh3)] shows Cu(II)/Cu(I) quasireversible redox couple while [AgX(L)(PPh3)] exhibits deposition of Ag(0) on the electrode surface together with irreversible ligand reduction. Coulometric oxidation of [CuX(L)(PPh3)] has synthesised copper(II) derivatives. Theoretical calculations are applied in modelling of complexes studied and UV-Vis spectra simulation. (C) 2013 Elsevier B.V. All rights reserved.
• Palladium(II) and platinum(II) complexes of N-{(2-pyridyl)methyliden}-6-coumarin and N-{(2-hydroxy)benzyliden}-6-coumarin
  作者：Suman Roy、Rajat Saha、Tapan Kumar Mondal、Chittaranjan Sinha

  DOI：10.1016/j.ica.2014.07.014

  日期：2014.11

  N-(2-pyridyl) methyliden}-6-coumarin (N,N' chelator; N,N' refer to N(pyridyl) and N(imine), respectively) and N-(2-hydroxy) benzyliden}-6-coumarin (N, O chelator; N, O refer to N(pyridyl) and O(phenolato)) have been used to synthesize palladium(II) and platinum(II) complexes - [ M(N,N')Cl-2], [M(N,O)(2)], [M(N,N')(2)](ClO4)(2) and [M(N,N')(N,O)]ClO4 (M = Pd, Pt). These complexes have been characterized by spectroscopic techniques (FTIR, UV-Vis, Mass, NMR) and the structural confirmation has been achieved in case of two representative complexes, [Pd(N,N')Cl-2] and [Pd(N,O)(2)] by the single crystal X-ray diffraction studies. The complexes emit at 409-557 nm and life times are in the range 0.52-1.98 ns. The cyclic voltammetric data of the complexes show the reduction of chelated ligand. The electronic configuration of the complexes is assessed by DFT computation and the spectral and redox properties are explained by TD-DFT calculation. (C) 2014 Elsevier B. V. All rights reserved.