2-(o-methylphenylazo)pyrimidine | 242485-68-3

• 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: 2-(o-methylphenylazo)pyrimidine
• 英文别名: 2-(o-tollylazo)pyrimidine；2-(o-tolylazo)pyrimidine；(2-methylphenyl)-pyrimidin-2-yldiazene
• CAS: 242485-68-3
• 化学式: C₁₁H₁₀N₄
• 分子量: 198.227
• InChiKey: NKBRUYLJPIWMJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  50.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tris(triphenylphosphine)ruthenium(II) chloride 、 2-(o-methylphenylazo)pyrimidine 以 二氯甲烷 为溶剂， 生成 dichlorobis(triphenylphosphine)[2-(o-methylphenylazo)pyrimidine]ruthenium(II)
  参考文献：
  名称：

  Reaction of Ru(PPh3)3Cl2 with 2-(arylazo)pyrimidines. Spectral and redox characterisation of the products.

  摘要：

  Reaction of 2-(arylazo)pyrimidine (aapm) with Ru(PPh3)(3)Cl-2 in CH2Cl2 solution affords [Ru(PPh3)(2)(aapm)Cl-2] (2) while the reaction under refluxing conditions in EtOH isolates [Ru(PPh3)(2)(aapm)(2)](ClO4)(2).H2O (3/4). Single crystal X-ray diffraction study of dichloro-bis(triphenylphosphine){2-(phenylazo)pyrimidine} ruthenium(II) has assigned a cis-Ru(PPh3)(2) motif to the complex. Isomers of [Ru(PPh3)(2)(aapm)](ClO4)(2) have been characterised by H-1 NMR data and they exist in cis-tians-cis and cis-cis-cis configurations in which coordination is considered with reference to three pairs of sequence of P, P (PPh3 abbreviated as P), N, N (N is N(pyrimidine)) and N ', N ' (N ' is N(azo)). The complexes exhibit MLCT transitions in the visible region. Redox studies show the Ru(III)/Ru(II) couple is in the range 0.8-1.2 V vs. SCE and [Ru(PPh3)(2)(aapm)(2)](ClO4)(2) exhibits a higher potential value than that of [Ru(PPh3)(2)(aapm)Cl-2]. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0277-5387(00)00655-0

文献信息

• Chemistry of azopyrimidines
  作者：Prasanta Kumar Santra、Debasis Das、Tarun Kumar Misra、Ramkrishna Roy、Chittaranjan Sinha、Shie-Ming Peng

  DOI：10.1016/s0277-5387(99)00085-6

  日期：1999.5

  2-(Arylazo)pyrimidines (aapm, 3) have been synthesized by condensing nitrosoaromatics with 2-aminopyrimidine. They yield cationic bis-chelated complexes with copper(I), Cu(aapm)2+ and are isolated as perchlorate salts. The complexes are 1:1 electrolytes in MeOH and exhibit intense MLCT transitions in the visible region. The NN stretch in copper(I) complexes shows a large shift to lower frequency (approx

  通过将亚硝基芳族化合物与2-氨基嘧啶缩合，合成了2-（芳基偶氮）嘧啶（aapm，3）。它们产生具有铜（I），Cu（aapm）2 +的阳离子双螯合络合物，并以高氯酸盐的形式分离。该络合物是在MeOH中的1：1电解质，并在可见光区域表现出强烈的MLCT转变。由于d（Cu）→π *（aapm ），铜（I）配合物中的NN展宽从游离配体值（约1425 cm -1）向较低频率（约1315 cm -1）有很大的偏移。）背面粘接。配合物显示高度拆分的对称1 H NMR光谱。在MeOH中，Cu（aapm）2 2+ / Cu（aapm）2 +一对大约在E 1/2处出现。在298 K下相对于SCE为0.7V。该结构已通过X射线晶体学证实。
• Osmium–azopyrimidine chemistry. Part VII: synthesis, structural characterisation and electrochemistry
  作者：S. Senapoti、U.S. Ray、P.K. Santra、C. Sinha、Alexandra M.Z. Slawin、J.Derek Woollins

  DOI：10.1016/s0277-5387(02)00833-1

  日期：2002.4

  Reaction of 2-(arylazo)pyrimidines (RC6H4NNC4H3N2, abbreviated aapm; R=H (papm), o-Me (o-tapm), m-Me (m-tapm), p-Me (p-tapm), p-Cl (p-Clpapm)) with (NH4)2[OsCl6] in 2-methoxyethanol gives two isomers of composition OsCl2(aapm)2. They are structurally characterised by 1H NMR spectra and established as the cis–trans–cis (ctc) and cis–cis–cis (ccc) isomer. With reference to the coordination pairs

  的2-反应（芳基偶氮）嘧啶（RC 6 ħ 4 NNC 4 ħ 3 Ñ 2，缩写为AAPM; R = H（PAPM），Ô -Me（ø -tAPM），米-Me（m -tAPM），p -Me（p -tAPM），p -Cl（p -ClpAPM））与（2-甲氧基乙醇中的（NH 4）2 [OsCl 6 ]）制得两种组成为OsCl 2（aAPM）2的异构体。它们通过1 H NMR光谱进行结构表征，并确定为顺式–反式-顺式（ctc）和顺式-顺式-顺式（ccc）异构体。关于Cl的配位对；通过X射线衍射研究确认了ctc -OsCl 2（p -tAPM）2的结构为N（嘧啶）（N）和N（偶氮）（N'）。该复合物在可见光到近红外区域表现出多个MLCT跃迁。氧化还原研究表明，与SCE相比，在1.2–1.3 V时有Os（III）/ Os（II）耦合，在〜2 V时有Os（IV）/ Os（III）耦合。EHMO计算
• Synthesis, spectral and electrochemical studies of 2-(arylazo)heterocycle complexes of zinc(II). Single-crystal X-ray structure of [Zn(papm)Cl2·CH3OH] (papm=2-(phenylazo)pyrimidine)
  作者：Jiban Kumar Nag、Prasanta Kumar Santra、Chittaranjan Sinha、Fen-Ling Liao、Tian-Huey Lu

  DOI：10.1016/s0277-5387(01)00824-5

  日期：2001.7

  2-(Arylazo)pyridines (aap) (R-C6H4-N=N-C5H4N, 1) and 2-(arylazo)pyrimidines (aapm) (R-C6H4-N=N-C4H3N2, 2); R = H (a), o-Me (b), m-Me (c), p-Me (d), p-Cl (e) are used to synthesise title compounds. The complexes are characterised by elemental analyses, IR, UV-Vis and H-1 NMR spectral data. Single-crystal X-ray structure of dichloro-2-(phenylazo)pyrimidinelzine}-zinc(II)(.)methanol suggests that the complex is a distorted trigonal bipyramidal symmetric around Zn(II), and Cl(1), Cl(2), N(4) (N (azo)) make the trigonal plane. Zn(II) moves downwards by 0.12 Angstrom from the centre of gravity of the plane. Two axial positions are occupied by N(1) (N(pyrimidine)) and methanol-O. Molecular packing shows one-dimensional infinite chain via hydrogen bonding. The EHMO calculation has been carried out to explain the electronic behaviour of the complexes and the results are compared with that of copper(I) complex. (C) 2001 Elsevier Science Ltd. All rights reserved.