3-nitro-1,5-di-p-chlorophenylformazan

• 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-di-p-chlorophenylformazan
• 英文别名: 3-nitro-1,5-dip-chlorophenylformazan；N'-(4-chloroanilino)-N-(4-chlorophenyl)imino-1-nitro-N-oxido-N-oxomethanimidamide
• 化学式: C₁₃H₉Cl₂N₅O₂
• 分子量: 338.153
• InChiKey: GOKHYVPGRILSNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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-di-p-chlorophenylformazan 在 ammonium sulfide 作用下， 生成
  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：

  硝基甲烷 、 对氯苯胺 在 盐酸 、 sodium nitrite 作用下， 生成 3-nitro-1,5-di-p-chlorophenylformazan
  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

文献信息

• 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.
• Sharma, Rajeev; Kalia, K. C., Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1995, vol. 34, # 11, p. 915 - 917
  作者：Sharma, Rajeev、Kalia, K. C.

  DOI：——

  日期：——
• Sharma, Rajeev; Devgan, Mona; Kalia, Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1996, vol. 35, # 1, p. 63 - 65
  作者：Sharma, Rajeev、Devgan, Mona、Kalia

  DOI：——

  日期：——
• Femtosecond Laser Spectroscopy and DFT Studies of Photochromic Dithizonatomercury Complexes
  作者：Karel G. von Eschwege、Gurthwin Bosman、Jeanet Conradie、Heinrich Schwoerer

  DOI：10.1021/jp410186y

  日期：2014.2.6

  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.