2-(tolylazo)imidazole | 34938-48-2

• 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-(tolylazo)imidazole
• 英文别名: 1-methyl-2-(phenylazo)imidazole；2-(p-tolylazo)imidazole；2-(p-tolyllazo)imidazole；MeaaiH；2-(p-Tolylazo)-1H-imidazole；1H-imidazol-2-yl-(4-methylphenyl)diazene
• CAS: 34938-48-2
• 化学式: C₁₀H₁₀N₄
• 分子量: 186.216
• InChiKey: LOIZASNBZZOZHA-UHFFFAOYSA-N

物化性质

• 熔点：
  235 °C(Solv: ethanol (64-17-5))
• 沸点：
  370.9±35.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  53.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(tolylazo)imidazole 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 生成 1H-imidazol-3-ium-2-yl-(4-methylphenyl)diazene;chloride
  参考文献：
  名称：

  Arylazoimidazoliumchloride and chlorometallates: Spectroscopic and structural characterization

  摘要：

  Protonation or dialkylation of 2-(arylazo)imidazoles (RaaiH) has generated azoimidazolium motif (RaaiH(2)(+), RaaiR'H+, RaaiR(2)'(+) where R = H, CH3 and R' = Me, Et, -CH2Ph). Electrostatic attraction between imdazolium cation and counter ions like Cl, ZnCl42-, PtCl62- has generated hydrogen bonded azoimidazolium-chloride/chlorometallated networks. The single crystal X-ray structure of 1-benzyl-2-(phenylazo) imidazolium chloride shows tape like 1-D network of [Cl(H2O)(4)]. Aquated Cl forms 10 membered supracycle through hydrogen bonding with imidazolium ion. The X-ray structures of [HaaiMe(2) (1,3)](+)[Me2NH2](+) [ZnCl4](2) and [MeaaiH(2)(+)center dot H2O](2)[PtCl6](2) show hydrogen bonded chlorometallate chain penetrated into the channel developed by organic motif. Azoimidazolium units are associated through pi center dot center dot center dot pi and C-H center dot center dot center dot pi interactions to strengthen the supramolecular geometry. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2010.02.006
• 作为产物：
  描述：

  咪唑 、 乙烷,三氯氟- 在 盐酸 、 sodium nitrite 、 sodium carbonate 作用下， 以 水 为溶剂， 生成 2-(tolylazo)imidazole
  参考文献：
  名称：

  Influence of the cavity size of cyclodextrins on the photochromism of azoimidazoles

  摘要：

  DOI：

  10.1016/j.jics.2021.100295

文献信息

• Copper coordination compounds of chelating imidazole-azo-aryl ligand. The molecular structures of bis[1-ethyl-2-(p-tolylazo)imidazole]-bis-(azido)copper(ii) and bis[1-methyl-2-(phenylazo)imidazole]-bis(thiocyanato)copper(ii)
  作者：Umasankar Ray、Debasis Banerjee、Golam Mostafa、Tian-Huey Lu、Chittaranjan Sinha

  DOI：10.1039/b406445c

  日期：——

  Reaction of Cu(ClO4)2 6H2O with 1-alkyl-2-(arylazo)imidazole [RaaiR′ where R = H (a), Me (b); R′ = Me (1), Et (2)] and NaN3/NH4SCN (1 ∶ 2 ∶ 2 mole ratio) form mononuclear complexes [Cu(RaaiR′)2(N3)2] (3,4) and [Cu(RaaiR′)2(SCN)2]. DMF (5,6). The complexes are characterized by elemental, spectral, electrochemical and other physicochemical results. The structures of both the complexes are confirmed by

  Cu（ClO 4）2 6H 2 O与1-烷基-2-（芳基偶氮）咪唑[RaaiR'的反应，其中R = H（a），Me（b）; R'= Me（1），Et（2）]和NaN 3 / NH 4 SCN（1：2：2摩尔比）形成单核络合物[Cu（RaaiR'）2（N 3）2 ]（3,4）和[Cu（RaaiR'）2（SCN）2 ]。DMF（5,6）。该复合物的特征在于元素，光谱，电化学和其他物理化学结果。两种配合物的结构均通过单晶X射线衍射[Cu（MeaaiEt）2（N 3）2 ]（4b）和[Cu（HaaiMe）2（SCN）2 ]的研究。DMF（5a）。配合物被还原为[铜（RaaiR'）2 ] +通过抗坏血酸。然而，空气氧化物[Cu（MeaaiEt）2 ]（CLO 4在N存在）3 - / SCN -产生[铜（MeaaiEt）2（N 3 / NCS）2 ]。
• Syntheses and characterization of η5-cyclopentadienyl and η5-indenyl ruthenium(II) complexes of arylazoimidazoles: The molecular structure of the complex [(η5-C5H5)Ru(PPh3)(C6H5–N N–C3H3N2)]+
  作者：Padavattan Govindaswamy、Chittaranjan Sinha、Mohan Rao Kollipara

  DOI：10.1016/j.jorganchem.2005.04.042

  日期：2005.7

  R′ = CH3 (3), R = H, R′ = C2H5 (4), R = CH3, R′ = H (5), R, R′ = CH3 (6), R = CH3, R′ = C2H5 (7)}. The complex [(η5-C9H7)Ru(PPh3)2(CH3CN)]+ (8) undergoes reactions with a series of N,N-donor azo ligands in methanol yielding complexes of the type [(η5-C9H7) Ru(PPh3)(RaaiR′)]+ where R, R′ = H (9), R = H, R′ = CH3 (10), R = CH3, R′ = H (11), R = CH3, R′ = C2H5 (12)}, respectively. These complexes were characterized

  络合物[（η 5 -C 5 H ^ 5）的Ru（PPH 3）2 CL]（1）具有若干arylazoimidazole（RaaiR'）配位体，即发生反应，2-（苯偶氮基）咪唑（班派-H），1-甲基-2-（苯基偶氮）咪唑（Phai-Me），1-乙基-2-（苯基偶氮）咪唑（Phai-Et），2-（甲苯基）咪唑（Tai-H），1-甲基-2-（甲苯基基）咪唑（大-ME）和1-乙基-2-（tolylazo）咪唑（泰-ET），得到的类型的配合物[（η 5 -C 5 H ^ 5）的Ru（PPH 3）（RaaiR'）] + 其中R，R'= H（2），R = H，R'= CH 3（3），R = H，R'= C 2 H在图5（4）中，R ＝ CH 3，R′＝ H（5），R，R′＝ CH 3（6），R ＝ CH 3，R′＝ C 2 H 5（7）}。络合物[（η 5 -C 9 ħ 7）的Ru（PPH 3）2（CH
• Synthesis, structure, photochromism, mesogenic property and DFT computations of silver(I) complexes of long chain alkyl group containing 1-alkyl-2-(arylazo)imidazoles
  作者：Avijit Nandi、Chandana Sen、Suman Roy、Debasish Mallick、Randhir Sinha、Tapan Kumar Mondal、Chittaranjan Sinha

  DOI：10.1016/j.poly.2014.04.066

  日期：2014.9

  The complexes [Ag(Raai-C-n,H2n+1)]ClO4 (where Raai-CnH2n+1 refer to 1-alkyl-2-(arylazo)imidazoles; R = H, Me and n = 4-22 (even numbers)) have been characterized by spectroscopic studies (UV-Vis, FT-IR, H-1 NMR). The X-ray structure of [Ag(Haai-C22H45)(2)]ClO4 confirms a distorted tetrahedral geometry. UV light irradiation (365-370 nm) of an acetonitrile solution of [Ag(Raai-CnH2n+1)(2)]ClO4 shows E-to-Z (trans-to-cis) isomerization of the coordinated Raai-CnH2n+1 group. The reverse transformation, Z-to-E (cis-to-trans), is very slow upon visible light irradiation, but becomes significantly faster on increasing the temperature (298-313 K). The rates and quantum yields (phi(E -> Z)) of the E-to-Z isomerization of the free ligands are higher than those of the complexes, which have proved the effect of rotor volume, rotor mass and the 1-alkyl chain length (-CnH2n+1)center dot[Ag(Haai-C18H37)(2)]ClO4 shows a metallomesogenic property and undergoes phase transitions: the Cr (46.7 degrees C) - SmC (106.4 degrees C) - I phase sequence on heating and I (106.4 degrees C) - SmA (46.4 degrees C) - Cr on cooling. The SmC phase appears as the typical fan-shaped texture. DFT computations on the optimized structure were carried out to explain the spectral properties. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis, Crystal Structure and Spectroscopic characterisation of Two Naphthylmethyl Derivatives Tolylazoimidazole
  作者：Shuang-Shuang Jiang、Jiang-Hong Qiu、Chuan-Ming Jin

  DOI：10.3184/174751914x14029239059340

  日期：2014.7

  Two tolylazoimidazole derivatives, N-1-(2-naphthylmethyl)-2-(p-tolylazo) imidazole and N-1,N-3-bis(2-naphthylmethyl)-2-(p-tolylazo) imidazolium perchlorate containing the 2-naphthylmethyl substituted groups were prepared and characterised by EA, IR, ESI-MS and NMR spectroscopy. The crystal structure of N-1,N-3-bis(2-naphthylmethyl)-2-(p-tolylazo) imidazolium perchlorate was determined by X-ray diffraction. The photo responsive results showed that N-1-(2-naphthylmethyl)-2-(p-tolylazo) imidazole present perfectly reversible trans-cis photoisomerisation by irradiation at 365 nm and 456 nm, with significantly lower quantum yield 0.19 and 0.04. However, N-1,N-3-bis(2-naphthylmethyl)-2-(p-tolylazo) imidazolium perchlorate does not undergo photoisomerisation.
• Arylazoimidazole compounds of rhenium nitrosyl: Synthesis, spectral characterization and reactivity
  作者：Pampa Pratihar、Anup Kumar Dasmahapatra、Chittaranjan Sinha

  DOI：10.1016/j.poly.2006.10.029

  日期：2007.4

  Reductive nitrosylation of ReO4- in aqueous alkaline medium by NH2OH center dot HCl furnishes the Re(NO)(3+) moiety which reacts with arylazoimidazoles to give hitherto unknown arylazoimidazole (RaaiR') complexes of rhenium nitrosyl, [Re(NO)(OH)(3)(RaaiR')]. The complexes are non-electrolytes in CH3CN. They exhibit upsilon(NO) at ca. 1700 cm(-1) and are magnetically active. The ESR profiles in the polycrystalline state at 298 K show (g(av)) approximate to 2.0. A spin forbidden ESR transition (Delta M-s = 2, g similar to 4) is observed at <1600 Gauss. A well defined sextet due to the metal hyperfine structure is observed. The complexes exhibit a moderately intense visible band at 440-450 nm which may be ascribed to a metal-to-ligand charge transfer transition, along with intraligand charge transfer, pi ->-> pi* and n ->-> pi*, transitions at <400 nm. Cyclic voltammetry exhibits quasireversible to irreversible metal oxidation and ligand reductions. The reaction of [Re(NO)(OH)(3)(RaaiR')] with camphor in alkaline medium has assisted C-N bond fusion by synthesizing a camphorquinone monoxime complex. (C) 2006 Elsevier Ltd. All rights reserved.