B3O3Ph3(pyridine) | 87826-13-9

• 英文名称: B3O3Ph3(pyridine)
• 英文别名: triphenylboroxine*pyridine；triphenylboroxine(pyr)
• CAS: 87826-13-9
• 化学式: C₂₃H₂₀B₃NO₃
• 分子量: 390.85
• InChiKey: YTQNRKNNQDWFOK-UHFFFAOYSA-N

反应信息

• 作为产物：
  描述：

  苯硼酸 以 丙酮 为溶剂， 反应 7.0h， 生成 B3O3Ph3(pyridine)
  参考文献：
  名称：

  Solid‐State Synthesis of B←N Adducts by the Amine‐Facilitated Trimerization of the Phenylboronic Acid

  摘要：

  Stable boroxine‐amine adducts comprising dative B←N bond(s) were prepared by mechanochemically‐induced reactions of phenylboronic acid (PBA) and amines (pyridine, DMAP, 1H‐pyrazole, piperidine, DABCO, hexamethylenetetramine, or 4,4’‐bipyridine). In‐situ Raman monitoring, ex‐situ PXRD and DFT calculations were used for product identification. Stoichiometry of the product (3 : 1, 3 : 2 or 6 : 1 adduct) was controlled by the amine structure and the molar ratio of the reactants. The 1 : 2 H‐bonded assembly of PBA and 4,4’‐bipyridine (bpy) was confirmed as an intermediate in the adduct formation for bpy. Competitive binding experiments indicated that the exchange of the amines in the 3 : 1 adducts follows the computed adduct stabilities that increase with the amine basicity. Following the DFT prediction, the first adduct with two different amines, DMAP and pip, bound to one boroxine moiety was isolated and structurally characterized. Results show that calculations can be used to predict possible and preferred product(s) and their spectral characteristics.

  DOI：

  10.1002/chem.202400190

文献信息

• B₃O₃Ph₃(7-azaindole):  Structure, Luminescence, and Fluxionality
  作者：Q. G. Wu、Gang Wu、Lorenzo Brancaleon、Suning Wang

  DOI：10.1021/om990053t

  日期：1999.6.1

  A 7-azaindole adduct of boroxine, B3O3Ph3(7-azaindole), 1, was obtained from the reaction of PhB(OH)2 with 7-azaindole. The crystal structure of 1 shows that the 7-azaindole ligand is bonded to the boroxine molecule through a B−N bond and an H···O hydrogen bond. Compound 1 is fluorescent in solution and the solid state. There is, however, a dramatic difference in the emission maximum of the solution

  由PhB（OH）2与7-氮杂吲哚的反应获得了环硼氧烷的7-氮杂吲哚加合物B 3 O 3 Ph 3（7-氮杂吲哚）1。的晶体结构1示出了7-氮杂吲哚配体通过一个B-N键和H···O氢键键键合至环硼氧烷分子。化合物1在溶液和固态中是荧光的。但是，溶液（λmax = 368 nm）和固体（λmax = 400 nm）光谱的发射最大值存在显着差异。的溶液行为1通过检查1 1 H NMR光谱法，建立该化合物图1的溶液是高通量的，这归因于分子间的7-氮杂吲哚配体解离/缔合过程，其活化能为34±1.5 kJ mol - 1。为了确定氢键在1的动态过程中的作用，还检查了B 3 O 3 Ph 3（Py）2的结构和溶液行为。在溶液中，化合物2经历类似于化合物1的分子间交换过程，其活化能为39±1.5 kJ mol - 1。1中相对较小的活化能 可以归因于氢键和7-氮杂吲哚相对于吡啶的降低的碱强度。
• Ring strain in boroxine rings: computational and experimental considerations
  作者：Jens Beckmann、Dainis Dakternieks、Andrew Duthie、Allan E.K Lim、Edward R.T Tiekink

  DOI：10.1016/s0022-328x(01)01060-9

  日期：2001.8

  B3LYP/6-311 + G(d) calculations indicate that (HBO)(3) (4) and (HBO)(4) (5) possess (zero-point energy corrected) strain enthalpies of 11.4 and 31.6 kJ mol(-1) respectively. The absence of eight-membered (RBO)(4) rings is attributed to a combination of ring strain and the lability of the B-O bond. The synthesis, characterization and molecular structure of (PhBO)(3). pyridine (1) are described and chemical phenomena related to the addition of amines to triorganoboroxine rings are rationalized in terms of relief of ring strain in 4. (C) 2001 Elsevier Science B.V. All rights reserved.
• Effect of Para-Substituents and Solvent Polarity on the Formation of Triphenylboroxine·Amine Adducts
  作者：Jeremy Kua、Matthew N. Fletcher、Peter M. Iovine

  DOI：10.1021/jp062055e

  日期：2006.7.1

  Density functional theory (B3LYP//6-311+G*) calculations including Poisson-Boltzmann implicit solvent and NMR were used to study the formation of a series of para-substituted triphenylboroxine, amine adducts with respect to their phenylboronic acid monomers and free amine in solution. Our calculations suggest that the intermediate prior to forming trimer, amine is a dimer, amine adduct. Formation of dimer, amine can proceed via two pathways. Electron-donating substituents favor dimerization of two monomers before addition of the amine, and electron-withdrawing substituents favor formation of a monomer, amine adduct before addition of the second monomer. We also find that pi-electron acceptors destabilize formation of the dimer and trimer with respect to its monomers. Electron-withdrawing substituents favor adduct formation. Adduct formation is enthalpically stabilized by increasing the polarity of the solvent but differential solubility of the monomer compared to trimer, amine also has an effect on the equilibrium constant.