N,N''-1,4-phenylenebis[N,N'-dimethyl-N'-[4-[methyl(methylphenylamino)carbonyl]amino]phenyl]urea | 134682-62-5

• 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: N,N''-1,4-phenylenebis[N,N'-dimethyl-N'-[4-[methyl(methylphenylamino)carbonyl]amino]phenyl]urea
• 英文别名: 1,3-Dimethyl-1-[4-[methyl-[methyl-[4-[methyl-[methyl-[4-[methyl-[methyl(phenyl)carbamoyl]amino]phenyl]carbamoyl]amino]phenyl]carbamoyl]amino]phenyl]-3-phenylurea
• CAS: 134682-62-5
• 化学式: C₄₂H₄₆N₈O₄
• 分子量: 726.878
• InChiKey: UOWXUZAXTSMMAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  54
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  94.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N,N'-dimethyl-N,N'-p-phenylenedicarbamoyl chloride 、 N,N'-dimethyl-N-(4-methylaminophenyl)-N'-phenylurea 以50%的产率得到N,N''-1,4-phenylenebis[N,N'-dimethyl-N'-[4-[methyl(methylphenylamino)carbonyl]amino]phenyl]urea
  参考文献：
  名称：

  Electronic Interactions in Tertiary Oligophenylureas

  摘要：

  The syntheses, structures, and spectroscopy of a series of oligomeric tertiary oligophenylureas possessing one to five phenyl rings are reported. A convergent synthetic method employing tertiary monoamme and diamine building blocks is employed. NMR and molecular modeling are indicative of folded structures for all of the oligophenylureas in which adjacent phenyl rings have a splayed face-to-face geometry. NMR chemical shifts, absorption and emission maxima, and electrochemical oxidation potentials are all dependent upon the number of phenyl rings. The addition of a first inner phenyl has a pronounced effect on the chemical shifts, while a second and third inner phenyl have diminished effects. The oxidation potentials of the oligophenylureas display an abrupt decrease upon the addition of the second inner phenyl. The absorption and emission spectra are relatively insensitive to the addition of one to three inner phenyl rings. The electronic structures of the oligophenylureas possessing one to eight rings have been analyzed using ZINDO calculations. The frontier orbitals of the ureas with one to three phenyl rings are localized on a single phenyl ring (the inner ring for the three-ring urea), whereas the frontier orbitals of the higher oligomers are delocalized over two phenyl rings. In all cases, urea-localized n,pi* transitions are lower in energy than the phenyl-localized pi,pi* transitions. The changes in properties with added phenyl rings parallel those previously observed for multilayered cyclophanes; however, they are less pronounced because of weaker coupling between the phenyl rings of the oligophenylureas.

  DOI：

  10.1021/jp0448090

文献信息

• Electronic Interactions in Tertiary Oligophenylureas
  作者：Frederick D. Lewis、Todd L. Kurth、Grace B. Delos Santos

  DOI：10.1021/jp0448090

  日期：2005.3.1

  The syntheses, structures, and spectroscopy of a series of oligomeric tertiary oligophenylureas possessing one to five phenyl rings are reported. A convergent synthetic method employing tertiary monoamme and diamine building blocks is employed. NMR and molecular modeling are indicative of folded structures for all of the oligophenylureas in which adjacent phenyl rings have a splayed face-to-face geometry. NMR chemical shifts, absorption and emission maxima, and electrochemical oxidation potentials are all dependent upon the number of phenyl rings. The addition of a first inner phenyl has a pronounced effect on the chemical shifts, while a second and third inner phenyl have diminished effects. The oxidation potentials of the oligophenylureas display an abrupt decrease upon the addition of the second inner phenyl. The absorption and emission spectra are relatively insensitive to the addition of one to three inner phenyl rings. The electronic structures of the oligophenylureas possessing one to eight rings have been analyzed using ZINDO calculations. The frontier orbitals of the ureas with one to three phenyl rings are localized on a single phenyl ring (the inner ring for the three-ring urea), whereas the frontier orbitals of the higher oligomers are delocalized over two phenyl rings. In all cases, urea-localized n,pi* transitions are lower in energy than the phenyl-localized pi,pi* transitions. The changes in properties with added phenyl rings parallel those previously observed for multilayered cyclophanes; however, they are less pronounced because of weaker coupling between the phenyl rings of the oligophenylureas.