7-(4'-methylphenylazo)-8-hydroxyquinoline-5-sulfonic acid | 17809-13-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 7-(4'-methylphenylazo)-8-hydroxyquinoline-5-sulfonic acid
• 英文别名: 8-hydroxy-7-(4-tolyldiazenyl)quinoline-5-sulfonic acid；5-sulfo-7-(4-methylphenylazo)-8-hydroxyquinoline；7-(4-methylphenylazo)-5-sulfo-8-hydroxyquinoline；(4-methylphenylazo)-5-sulfo-8-hydroxyquinoline；7-(4-Methyl-phenylazo)-8-hydroxy-chinolin-5-sulfonsaeure；8-Hydroxy-7-[(4-methylphenyl)diazenyl]quinoline-5-sulfonic acid
• CAS: 17809-13-1
• 化学式: C₁₆H₁₃N₃O₄S
• 分子量: 343.363
• InChiKey: DWAHNQOFELMZPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  7-(4'-methylphenylazo)-8-hydroxyquinoline-5-sulfonic acid 、 copper(II) sulfate 以 ethanol 、 H₂O 为溶剂， 以74%的产率得到[Cu(8-hydroxy-7-(4-tolyldiazenyl)quinoline-5-sulfonic acid(-H))2]
  参考文献：
  名称：

  Highly selective colorimetric detection of cysteine and homocysteine in water through a direct displacement approach

  摘要：

  The complex CuQ(2) (HQ = 8-hydroxy-7-(4-tolyldiazenyl)quinoline-5-sulfonic acid) has been synthesized and used as a colorimetric probe for the specific detection of cysteine and homocysteine in water through a displacement reaction. The detection can be performed either by the spectroscopy from the increased UV-vis absorbance at 498 nm or by the change of color from yellow to red upon addition of cysteine or homocysteine to the solution of the complex. The experimental results show no interference by other amino acids to the detection of cysteine and homocysteine. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.inoche.2009.09.035
• 作为产物：
  描述：

  8-羟基喹啉-5-磺酸水合物 、 乙烷,三氯氟- 在 盐酸 、 sodium nitrite 、 potassium hydroxide 作用下， 以 水 、 乙醇 为溶剂， 以62%的产率得到7-(4'-methylphenylazo)-8-hydroxyquinoline-5-sulfonic acid
  参考文献：
  名称：

  Supramolecular structure and substituents effect on the spectral studies of dioxouranium(VI) azodyes complexes

  摘要：

  The synthesis of several coordination azo compounds of dioxouranium(VI) heterochelates with bidentate azo compounds derived from 4-alkylphenylazo-5-sulfo-8-hydroxyquinoline (HLn) ligands, are described. The ligands and structural composition of azo complexes were confirmed and characterized by various physico-chemical techniques. The bonding sites of the azo compounds are deduced from IR and H-1 NMR spectra and the ligands were found to bond to the UO22+ ion in a bidentate fashion. The ligands obtained contain N=N and phenolic functional groups in different positions with respect to the quinoline group. IR spectra show that the azo compounds (HLn) acts as a monobasic bidentate ligand by coordinating via the azo nitrogen atom of azodye (-N=N-) and oxygen atom of the phenolic group forming thereby a six-membered chelating ring and concomitant formation of an intramolecular hydrogen bond. The v(3) frequency of UO22+ has been shown to be an excellent molecular probe for studying the coordinating power of the ligands. The values of v(3) of the prepared complexes containing UO22+ were successfully used to calculate the force constant, F-UO (in 10-8 N/angstrom) and the bond length R-UO (in angstrom) of the U-O bond. A strategy based upon both theoretical and experimental investigations has been adopted. The theoretical aspects are described in terms of the well-known theory of 5d-4f transitions. Wilson's, matrix method, Badger's formula, and Jones and El-Sonbati equations were used to calculate the U-O bond distances from the values of the stretching and interaction force constants. The most probable correlation between U-O force constant to U-O bond distance were satisfactorily discussed in term of Badger's rule and the equations suggested by Jones and El-Sonbati. The effect of Hamette's constant is also discussed. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2011.08.036

文献信息

• Supramolecular spectral studies on metal–ligand bonding of novel quinoline azodyes
  作者：M.A. Diab、A.Z. El-Sonbati、A.A. El-Bindary、A.M. Barakat

  DOI：10.1016/j.saa.2013.07.053

  日期：2013.12

  A series of novel bidentate azodye quinoline ligands were synthesized with various p-aromatic amines like p-(OCH3, CH3, H, Cl and NO2). All ligands and their complexes have been characterized on the basis of elemental analysis, R-1, H-1 and C-13 NMR data and spectroscopic studies. IR and H-1 NMR studies reveal that the ligands (HL) exists in the tautomeric azo/hydrazo form in both states with intramolecular hydrogen bonding. The ligands obtained contain N=N and phenolic functional groups in different positions with respect to the quinoline group. IR spectra show that the azo compounds (HL) act as monobasic bidentate ligand by coordinating via the azodye (-N=N-) and oxygen atom of the phenolic group. The ESR (g(vertical bar vertical bar) and g(perpendicular to)) and bonding alpha(2) parameters of the copper ion were greatly affected by substituting several groups position of ring of quinoline and p-aromatic ring. The ESR spectra of copper complexes in powder form show a broad signal with values in order g(vertical bar vertical bar) > g(perpendicular to) > g(e) >2.0023. The value of covalency factor beta and orbital reduction factor K accounts for the covalent nature of the complexes. All complexes possessed an octahedral and square planar geometry. The thermal properties of the complexes were investigated using TGA and DSC. It is found that the change of substituent affects the thermal properties of complexes. (C) 2013 Elsevier B.V. All rights reserved.
• Supramolecular structure and substituents effect on the spectral studies of oxovanadium(IV) azodyes complexes
  作者：M.A. Diab、A.A. El-Bindary、A.Z. El-Sonbati、O.L. Salem

  DOI：10.1016/j.molstruc.2012.03.019

  日期：2012.6

  A series of novel bidentate azodye quinoline ligands were synthesized with various p-aromatic amines like p-(OCH3, CH3, H, Cl and NO2) in pyridine medium. All ligands have been characterized on the basis of elemental analysis, IR and H-1 NMR data. The ligands obtained contain N=N and phenolic functional groups in different positions with respect to the quinoline group. IR spectra show that the azo compounds (HLn) act as monobasic bidentate ligand by coordinating via the azo nitrogen atom of azodye (-N=N-) and oxygen atom of the phenolic group thereby forming a six-membered chelating ring and concomitant formation of an intramolecular hydrogen bond. Novel vanadium azodye complexes of these ligands with general formula [OV(L1-5)(2)(OH2)] have been prepared by interaction of vanadyl sulfate pentahydrate with DMF solution of the appropriate ligands. The resulting complexes have been characterized on the basis of elemental analysis, molar conductance and magnetic measurements, infrared and electronic spectral studies. Suitable distorted octahedral structures have been proposed for these complexes. The Hammett's constant is also discussed. (C) 2012 Elsevier B.V. All rights reserved.
• D.C. electrical conductivity and conduction mechanism of some azo sulfonyl quinoline ligands and uranyl complexes
  作者：N.A. El-Ghamaz、M.A. Diab、A.Z. El-Sonbati、O.L. Salem

  DOI：10.1016/j.saa.2011.07.042

  日期：2011.12

  Supramolecular coordination of dioxouranium(VI) heterochelates 5-sulphono-7-(4'-X phenylazo)-8-hydroxyquinoline HLn (n = 1, X= CH3; n=2, X= H; n =3, X= Cl; n = 4, X= NO2) have been prepared and characterized with various physico-chemical techniques. The infrared spectral studies showed a monobasic bidentate behavior with the oxygen and azonitrogen donor system. The temperature dependence of the D.C. electrical conductivity of HLn ligands and their uranyl complexes has been studied in the temperature range 305-415 K. The thermal activation energies E-a for HLn. compounds were found to be in the range 0.44-0.9 eV depending on the nature of the substituent X. The complexation process decreased E-a values to the range 0.043-045 eV. The electrical conduction mechanism has been investigated for all samples under investigation. It was found to obey the variable range hopping mechanism (VRH). (C) 2011 Elsevier B.V. All rights reserved.