-benzonitrile | 13137-55-8

• 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: -benzonitrile
• 英文别名: 2,4,6-trideuteriobenzonitrile；benzonitrile-2,4,6-d3；2,4,6-trideuterio-benzonitrile；Benzonitril<2,4,6-D(3)>；(2,4,6-²H3)Benzonitril；1-Cyan-2,4,6-trideutero-benzol
• CAS: 13137-55-8
• 化学式: C₇H₅N
• 分子量: 106.1
• InChiKey: JFDZBHWFFUWGJE-NHPOFCFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.56
• 重原子数：
  8.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.79
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  -benzonitrile 在 氢氧化钾 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 氢溴酸 作用下， 以 二甲基亚砜 为溶剂， 生成 4-bromobenzyl, benzyl-2,4,6-d3 ether
  参考文献：
  名称：

  Skeletal rearrangements on chemical ionization of dibenzyl ether and derivatives

  摘要：

  AbstractProtonated molecular ions of dibenzyl ether, formed by chemical ionization using hydrogen and isobutane as reagent gases, undergo skeletal rearrangements to lose water and formaldehyde, both in the ion source and the flight path. The rearrangements have been elucidated by deuterium labelling and chemical substitution. The water lost contains the reagent proton and an aromatic hydrogen atom, and the aromatic hydrogen atoms have been shown to be mobile prior to the reaction. It is proposed that the skeletal rearrangement for water loss is initiated by protonation on the ether oxygen atom, followed by benzyl migration. The formaldehyde lost contains benzylic hydrogen atoms exclusively, and it is proposed that the skeletal rearrangement is preceded by hydrogen rearrangement of an oxygen protonated molecular ion to a ring protonated molecular ion. Daughter ion structures are supported by comparisons of their collision induced dissociation spectra with those of isomeric ions prepared by alternative routes.

  DOI：

  10.1002/oms.1210161003
• 作为产物：
  描述：

  氰化钾 、 aniline-2,4,6,N-d6 deuterochloride 在 2.) CuCN 作用下， 生成 -benzonitrile
  参考文献：
  名称：

  Skeletal rearrangements on chemical ionization of dibenzyl ether and derivatives

  摘要：

  AbstractProtonated molecular ions of dibenzyl ether, formed by chemical ionization using hydrogen and isobutane as reagent gases, undergo skeletal rearrangements to lose water and formaldehyde, both in the ion source and the flight path. The rearrangements have been elucidated by deuterium labelling and chemical substitution. The water lost contains the reagent proton and an aromatic hydrogen atom, and the aromatic hydrogen atoms have been shown to be mobile prior to the reaction. It is proposed that the skeletal rearrangement for water loss is initiated by protonation on the ether oxygen atom, followed by benzyl migration. The formaldehyde lost contains benzylic hydrogen atoms exclusively, and it is proposed that the skeletal rearrangement is preceded by hydrogen rearrangement of an oxygen protonated molecular ion to a ring protonated molecular ion. Daughter ion structures are supported by comparisons of their collision induced dissociation spectra with those of isomeric ions prepared by alternative routes.

  DOI：

  10.1002/oms.1210161003

文献信息

• Association between polar molecules. Part 2.—Equilibrium and thermodynamic studies on the dipole association of benzonitrile derivatives with hexamethylphosphoramide, di-n-butyl sulphone, di-n-butyl sulphoxide and tetramethylurea in non-polar solvents
  作者：Hideaki Fujiwara、Tatsuya Takagi、Yutaka Yamazaki、Yoshio Sasaki

  DOI：10.1039/f19827800347

  日期：——

  Dipole association between p-substituted benzonitriles and polar substances such as hexamethylphosphoramide(HMPA), di-n-butyl sulphone(DBSN), di-n-butyl sulphoxide(DBSX) and tetramethylurea (TMU) is investigated in non-polar solvent by means of n.m.r. spectroscopy assuming the formation of a 1 : 1 associate between the polar molecules. Association parameters (association constant and association shift)

  在非极性溶剂中，研究了对取代的苄腈与极性物质（六甲基磷酰胺（HMPA），二正丁基砜（DBSN），二正丁基亚砜（DBSX）和四甲基脲（TMU）之间的偶极缔合。假设极性分子之间形成1：1缔合，则是nmr光谱分析的结果。结合偶极矩和取代基常数推导并讨论了缔合参数（缔合常数和缔合位移）。如所期望的，缔合常数取决于HMPA，DBSN，DBSX和TMU的偶极矩，还取决于p的取代基常数。取代的苄腈。但是，该常数与苄腈的偶极矩之间的相关性与预期的相反。苯甲腈的Ph-X片段的极化与C N键的极化相反，被认为是造成这种现象的原因。
• Photochemical Addition of 2,2,2-Trifluoroethanol to Benzonitrile and <i>p</i>-, <i>m</i>-, and <i>o</i>-Methylbenzonitrile
  作者：Jennifer Foster、Alexandra L. Pincock、James A. Pincock、Kim A. Thompson

  DOI：10.1021/ja982712j

  日期：1998.12.1

  lamps results in the formation of four addition products, the stereoisomers of 6-cyano-2-(2,2,2-trifluroethoxy)bicyclo[3.1.0]hex-3-ene, 22−25. The proposed mechanism begins by formation of the 6-cyanobicyclo[3.1.0]hex-3-en-2,6-diyl biradical/zwitterion from S1 followed by both endo and exo protonation by TFE at C6. Deuterium labeling demonstrated that the resulting 6-cyanobicyclo[3.1.0]hex-3-en-2-yl cation

  用低压汞灯发出的 254 nm 光照射 2,2,2-三氟乙醇 (TFE) 中的苯甲腈导致形成四种加成产物，即 6-cyano-2-(2,2,2-三氟乙氧基)双环[3.1.0]己-3-烯，22-25。所提出的机制开始于从 S1 形成 6-氰基双环 [3.1.0]hex-3-en-2,6-二基双自由基/两性离子，然后在 C6 处由 TFE 进行内质子化和外质子化。氘标记表明，得到的 6-氰基双环 [3.1.0] hex-3-en-2-yl 阳离子在被亲核溶剂捕获之前经历了快速简并 1,4-σ 重排，迁移碳的构型发生反转。对-和间-甲基苄腈以相同方式辐照得到六种主要加成产物。其中三个，32、33和35是6-氰基-2-(2,2,2-三氟乙氧基)-4-甲基双环[3。1.0]hex-3-enes 和其他三个，32、33 和 35，是 6-cyano-2-(2,2,2-trifluoroethoxy)-2-methylbicyclo[3