3-nitro-1,5-dip-tolylformazan | 28952-14-9

• 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: 3-nitro-1,5-dip-tolylformazan
• 英文别名: 3-Nitro-1,5-di-p-tolylformazan；N'-(4-methylanilino)-N-(4-methylphenyl)imino-1-nitro-N-oxido-N-oxomethanimidamide
• CAS: 28952-14-9
• 化学式: C₁₅H₁₅N₅O₂
• 分子量: 297.316
• InChiKey: LKZGISCSQMBLRH-UHFFFAOYSA-N

物化性质

• 沸点：
  454.4±48.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  94.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-nitro-1,5-dip-tolylformazan 在 ammonium sulfide 作用下， 生成 1,5-di-p-tolyl-thio carbonohydrazide
  参考文献：
  名称：

  Femtosecond Laser Spectroscopy and DFT Studies of Photochromic Dithizonatomercury Complexes

  摘要：

  The ultrafast dynamics of the photochromic reaction of dithizonatophenylmercury(II) was recently reported. For purpose of investigating the effect of electronically different substituents (X = o-F, m-F, p-F, p-Cl, o-CH3, m-CH3, p-CH3, m,p-diCH(3), p-OCH3, o-SCH3, and p-SCH3) on this reaction, a series of phenyl-substituted dithizones were synthesized and complexed with phenylmercury(II). A variation of more than 3 ps in ground state repopulation times was observed, with the o-methyl derivative absorbing both at shortest wavelength and having the fastest repopulation time, while the p-S-methyl derivative lies at the opposite extremity. An increase in both decay times and lambda(max) values is generally reflected by an increase in electron density in the chromophore. Ultrafast rates also proved to be dependent on solvent polarity, while a profound solvatochromic effect was observed in the transition state absorbance. Density functional theory realistically simulated isomer stabilities, electronic spectra and molecular orbitals. Increased electron density enhances stability in the photoexcited blue isomer relative to the orange resting state, as seen from a comparison between orange and blue isomer total bonding energies. A linear trend between computed HOMO energies and experimental lambda(max) of related aliphatic substituted derivatives was found.

  DOI：

  10.1021/jp410186y
• 作为产物：
  描述：

  4-甲基偶氮苯 、 硝基甲烷 在 sodium hydroxide 、 水 、 sodium acetate 作用下， 生成 3-nitro-1,5-dip-tolylformazan
  参考文献：
  名称：

  Synthesis of Di-beta-naphthylthiocarbazone and Some of its Analogs^*

  摘要：

  DOI：

  10.1021/ja01252a042

文献信息

• Convenient synthesis and antibacterial activity of novel 5-phenyldiazenyl-1,3,4-thiadiazole derivatives
  作者：Fatma M. Saleh、Mirna T. Helmy、Hamdi M. Hassaneen

  DOI：10.1080/10426507.2020.1858081

  日期：2021.5.4

  presence of triethylamine afforded the corresponding 1,3,4-thiadiazole derivatives 10, 11, 13, 14 and 22–29. Stirring of N,2-diaryldiazene-1-carbohydrazonoyl chlorides 1–3 with thioanilides 31A–E in acetonitrile at room temperature in the presence of triethylamine gave the corresponding 1,3,4-thiadiazol-2(3H)-ylidene derivatives 34–36. The structures of all new compounds 10, 11, 13, 14, 22–29 and 34–36

  摘要 的反应Ñ，2- diaryldiazene -1- carbohydrazonoyl氯化物1,2与2 - （（甲硫基）-carbonthioyl）腙7,12和18-21的无水乙醇在三乙胺，得到存在室温下相应的1,3- ，4-噻二唑衍生物10，11，13，14和22-29。在室温下，在三乙胺存在下，在乙腈中用硫代苯胺31A-E搅拌N，2-二芳基二氮杂-1-碳酰重氮酰氯1-3，得到相应的1,3,4-噻二唑-2（3 H）-亚烷基衍生物34 –36。所有新化合物的结构通过元素分析和光谱数据确定了10、11、13、14、22-29和34-36。研究了一些针对金黄色葡萄球菌和大肠杆菌的新合成化合物，最有效的化合物是3-苯基-5-（苯基二氮烯基）-2-（（1-（吡啶-2-基）亚乙基）hydr基）-2,3-二氢-1,3,4-噻二唑（13c），2-（（1-（吡啶-2-基）亚乙基）肼基）-3-（对甲苯基）-5-（对甲苯二重氮基）-2
• Synthesis and kinetics of electronically altered photochromic dithizonatophenylmercury(II) complexes
  作者：Karel G. von Eschwege

  DOI：10.1016/j.jphotochem.2012.11.009

  日期：2013.1

  A series of phenyl-substituted dithizones were synthesized, and preparation of the corresponding series of photochromic phenylmercury(II) complexes is for the first time reported. Adaption of previous methods enhanced synthesis convenience and product yields. A single crystal X-ray data collection of the ortho-S-methyl nitroformazan reaction intermediate was done. ADF computed molecular orbitals of the title compound show the HOMO and LUMO orbitals stretching along the entire ligand. The spontaneous back reaction kinetics of dithizonatophenylmercury(II) was studied at varied concentrations, temperatures and in different solvents. An exponential correlation was found between the rate of reverse isomerization and temperature, while increased solvent polarity and decreased molar mass facilitate higher return rates. The kinetic study of the series of twelve electronically altered complexes yielded a lowest rate of 0.0002 s(-1) the ortho-methyl derivative, while the highest rate of 0.0106 s(-1) was measured for the meta-methoxy derivative. (C) 2012 Elsevier B.V. All rights reserved.
• Synthesis and Kinetics of Sterically Altered Photochromic Dithizonatomercury Complexes
  作者：Ernestine Alabaraoye、Karel G. von Eschwege、Nagarajan Loganathan

  DOI：10.1021/jp5076324

  日期：2014.11.20

  Following a previous study where 12 electronically altered dithizones were synthesized, here we report on attempts to synthesize 26 dithizones. The purpose was to explore the boundaries within which dithizones may be synthesized, explore spectral tuning possibilities, and investigate steric effects on the photochromic reaction of its mercury complexes. Contrary to expectation, large substituents like phenoxy groups increased the rate of the photochromic back-reaction. In the series H-, 2-CH3-, 4-CH3-, 3,4-(CH3)(2-), 2-OC6H5-, and 4-OC6H5-dithizonatophenylmercury(II), the lowest rate of 0.0004 s(1) was measured for the 2-CH3 complex, while the rate for the 2-OC6H5 derivative was 20 times higher. A solvent study revealed a direct relationship between dipole moment and the rate of the back-reaction, while the relationship between temperature and rate is exponential, with t(1/2) = 2 min 8 s for the 4-phenoxy complex. The crystal structures of two dithizone precursors, 2-phenoxy- and 4-phenoxynitroformazan, are reported.
• Kalia, K. C.; Kumar, Anil; Singla, Meenakshi, Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical
  作者：Kalia, K. C.、Kumar, Anil、Singla, Meenakshi、Kaur, Tejinder

  DOI：——

  日期：——
• A NOVEL ONE-POT SYNTHESIS OF 3-ARYLAZO-[1,2,4]TRIAZOLO-[4,3-a]PYRIMIDIN-5(1H)-ONES
  作者：Ahmad S. Shawali、Ahmad H. Elghandour、Abdelwahed R. Sayed

  DOI：10.1081/scc-100103263

  日期：2001.1

  A novel synthesis of 3-arylazo-1,7-disubstituted [1,2,4]triazolo[4,3-a]pyrimidinone-5(1H)-ones 8 via reaction of 2-thiouracil derivatives 3 and 4 with either 3-chloro- or 3-nitro-1,5-diarylformazans is reported.