(E)-m-Stilbene-N-tert-butylhydroxylamine

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-m-Stilbene-N-tert-butylhydroxylamine
• 英文别名: N-tert-butyl-N-[3-[(E)-2-phenylethenyl]phenyl]hydroxylamine
• 化学式: C₁₈H₂₁NO
• 分子量: 267.371
• InChiKey: RCVFCCYPQFIJNW-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-m-Stilbene-N-tert-butylhydroxylamine 在 silver(l) oxide 作用下， 以 苯 为溶剂， 生成
  参考文献：
  名称：

  Semiempirical Investigation of Stilbene-Linked Diradicals and Magnetic Study of Their Bis(N-tert-butylnitroxide) Variants

  摘要：

  The electronic states of open-shell stilbene diradicals were st;hied. Previously used semiempirical MO-CI methods were applied to stilbenes having dimethylene, dioxyl, and dinitroxide centers in o,o'-, o,m'-, o,p'-, m,m'-, m,p'-, and p,p'-substitution patterns, and the various singlet-triplet energy gaps were computed to predict qualitative ground state spin multiplicities. Singlet and triplet spin states were essentially degenerate in the m,m'-isomers of disjoint connectivity, while nondisjoint o,m'- and m,p'-isomers had triplet computed ground states. Nitroxide-based diradicals showed considerably smaller computational exchange coupling energies than did other diradical models studied. As a tests of these computations, stilbenes with two N-tert-butyl nitroxide groups at the o,m'-, m,m'-, and m,p'-positions were prepared, and their magnetic properties were studied by ESR and-magnetic susceptibility measurements. The m,m'- and m,p'-isomers were found experimentally to have singlet and triplet ground states, respectively, in accord with the qualitative computed predictions.

  DOI：

  10.1021/jo00094a046
• 作为产物：
  描述：

  亚硝基叔丁烷 、 (E)-3-溴二苯乙烯 在 magnesium 、 1,2-二溴乙烷 作用下， 生成 (E)-m-Stilbene-N-tert-butylhydroxylamine
  参考文献：
  名称：

  Semiempirical Investigation of Stilbene-Linked Diradicals and Magnetic Study of Their Bis(N-tert-butylnitroxide) Variants

  摘要：

  The electronic states of open-shell stilbene diradicals were st;hied. Previously used semiempirical MO-CI methods were applied to stilbenes having dimethylene, dioxyl, and dinitroxide centers in o,o'-, o,m'-, o,p'-, m,m'-, m,p'-, and p,p'-substitution patterns, and the various singlet-triplet energy gaps were computed to predict qualitative ground state spin multiplicities. Singlet and triplet spin states were essentially degenerate in the m,m'-isomers of disjoint connectivity, while nondisjoint o,m'- and m,p'-isomers had triplet computed ground states. Nitroxide-based diradicals showed considerably smaller computational exchange coupling energies than did other diradical models studied. As a tests of these computations, stilbenes with two N-tert-butyl nitroxide groups at the o,m'-, m,m'-, and m,p'-positions were prepared, and their magnetic properties were studied by ESR and-magnetic susceptibility measurements. The m,m'- and m,p'-isomers were found experimentally to have singlet and triplet ground states, respectively, in accord with the qualitative computed predictions.

  DOI：

  10.1021/jo00094a046

文献信息

• Semiempirical Investigation of Stilbene-Linked Diradicals and Magnetic Study of Their Bis(N-tert-butylnitroxide) Variants
  作者：Naoki Yoshioka、Paul M. Lahti、Takashi Kaneko、Yoshihiro Kuzumaki、Eishun Tsuchida、Hiroyuki Nishide

  DOI：10.1021/jo00094a046

  日期：1994.7

  The electronic states of open-shell stilbene diradicals were st;hied. Previously used semiempirical MO-CI methods were applied to stilbenes having dimethylene, dioxyl, and dinitroxide centers in o,o'-, o,m'-, o,p'-, m,m'-, m,p'-, and p,p'-substitution patterns, and the various singlet-triplet energy gaps were computed to predict qualitative ground state spin multiplicities. Singlet and triplet spin states were essentially degenerate in the m,m'-isomers of disjoint connectivity, while nondisjoint o,m'- and m,p'-isomers had triplet computed ground states. Nitroxide-based diradicals showed considerably smaller computational exchange coupling energies than did other diradical models studied. As a tests of these computations, stilbenes with two N-tert-butyl nitroxide groups at the o,m'-, m,m'-, and m,p'-positions were prepared, and their magnetic properties were studied by ESR and-magnetic susceptibility measurements. The m,m'- and m,p'-isomers were found experimentally to have singlet and triplet ground states, respectively, in accord with the qualitative computed predictions.