Benzonitrile-BF3 | 456-29-1

• 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-BF3
• 英文别名: benzylidyneazaniumyl(trifluoro)boranuide
• CAS: 456-29-1
• 化学式: C₇H₅BF₃N
• 分子量: 170.93
• InChiKey: LHBOIHYWLRWMIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  4.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  trifluoro(α-benzil monoxime)boron(III) 以 neat (no solvent) 为溶剂， 生成 Benzonitrile-BF3
  参考文献：
  名称：

  肟卤化物的反应。第三部分 α-苯并一肟和乙酰基一肟与苯基二氯化硼和三氟化硼，-氯化物和-溴化物

  摘要：

  摘要三氟化硼与α-苯并一肟（bmoH）反应生成BF 3，bmoH。用三氯化硼和三溴化物使肟生成BX 2（bmo）（X = Cl或Br），用苯基二氯化硼生成PhBCl（bmo）。从乙酰一肟（amoH）获得类似的络合物。络合物BX 2（bmo）不受水的影响，但被温暖的碱水解。所有其他复合物都被水水解。加合物BF 3，bmoH在120°C / 0.1 mm加热时发生贝克曼断裂，但在120dg / 460 mm加热时发生贝克曼重排；其他配合物在加热时发生贝克曼裂解。质谱研究表明，配合物BCl 2（bmo）和BX 2（amo）在蒸汽状态下是二聚体。

  DOI：

  10.1016/s0020-1693(00)94981-8
• 作为试剂：
  描述：

  4-辛炔 、 [(N-tosylimino)iodo]benzene 、 苯甲腈 在 Benzonitrile-BF3 作用下， 反应 4.0h， 以49%的产率得到2-phenyl-4,5-dipropyl-1-tosyl-1H-imidazole
  参考文献：
  名称：

  含金属的[2 + 2 + 1]环烷基，腈和氮原子的碘代碘化物，用于合成高度取代的咪唑

  摘要：

  三氟化硼腈络合物可促进亚氨基碘的炔烃，腈和N-原子的[2 + 2 + 1]氧化环化反应，从而以中等至良好的收率得到相应的2,4-二取代和2,4,5-三取代的N-甲苯磺酰咪唑，高区域选择性。

  DOI：

  10.1002/adsc.201500032

文献信息

• Condensed-Phase Effects on the Structural Properties of C₆H₅CN−BF₃ and (CH₃)₃CCN−BF₃:  IR Spectra, Crystallography, and Computations
  作者：J. A. Phillips、D. J. Giesen、N. P. Wells、J. A. Halfen、C. C. Knutson、J. P. Wrass

  DOI：10.1021/jp052495q

  日期：2005.9.1

  Condensed-phase effects on the structure and bonding of C6H5CN-BF3 and (CH3)(3)CCN-BF3 are illustrated by a variety of results, and these are compared to analogous data for the closely related complex CH3CNBF3. For the most part, the structural properties Of C6H5CN-BF3 and (CH3)(3)CCN-BF3 are quite similar, not only in the gas phase but also in the solid state and in argon matrices. However, the structures do change significantly from medium to medium, and these changes are reflected in the data presented below. Specifically, the measured crystallographic structure Of C6H5CN-BF3 (s) has a B-N distance that is 0.17 Alpha shorter than that in the equilibrium gas-phase structure obtained via B3LYP calculations. Notable differences between calculated gas-phase frequencies and measured solid-state frequencies for both C6H5CN-BF3 and (CH3)(3)CCN-BF3 were also observed, and in the case of (CH3)(3)CCN-BF3, these data implicate a comparable difference between solid-state and gas-phase structure, even in the absence of crystallographic results. Frequencies measured in argon matrices were found to be quite similar for both complexes and also very near those measured previously for CH3CN-BF3, suggesting that all three complexes adopt similar structures in solid argon. For C6H5CN-BF3 and (CH3)(3)CCN-BF3, matrix IR frequencies differ only slightly from the computed gas-phase values, but do suggest a slight compression of the B-N bond. Ultimately, it appears that the varying degree to which these systems respond to condensed phases stems from subtle differences in the gas-phase species, which are highlighted through an examination of B-N distance potentials from B3LYP calculations. The larger organic substituents appear to stabilize the potential near 1.8 Alpha, so that the structures are more localized in that region prior to any condensed-phase interactions. As a result, the condensed-phase effects on the structural properties Of C6H5CN-BF3 and (CH3)(3)CCN-BF3 are much less pronounced than those for CH3CN-BF3.