2-(o-tolyliminomethyl)phenylboronic acid | 1373320-86-5

• 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: 2-(o-tolyliminomethyl)phenylboronic acid
• 英文别名: [2-[(2-Methylphenyl)iminomethyl]phenyl]boronic acid；[2-[(2-methylphenyl)iminomethyl]phenyl]boronic acid
• CAS: 1373320-86-5
• 化学式: C₁₄H₁₄BNO₂
• 分子量: 239.082
• InChiKey: BTBCUAUIEQZNSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.43
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  52.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(o-tolyliminomethyl)phenylboronic acid 在 sodium tetrahydroborate 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 2.5h， 以80.6%的产率得到2-(o-tolylaminomethyl)phenylboronic acid
  参考文献：
  名称：

  Imino- and aminomethylphenylboronic acids: stabilizing effect of hydrogen bonds

  摘要：

  ortho-Iminomethylphenylboronic acids were synthesized from the reaction of 2-formyl-phenylboronic acid with primary aromatic amines. Reduction of these compounds yielded the corresponding aminomethylphenylboronic acids. For both types of the compounds, the crystal structure was determined by single crystal X-ray diffraction method. Hydrogen-bonded dimers with an additional intramolecular B-O-H center dot center dot center dot N hydrogen bond have been observed. Calculations at MP2/6-31+G** level proved that the most stable form is that with the above-mentioned intramolecular hydrogen bond while the form with dative N -> B bond is less favoured. Since the calculated energy difference is small, the competition between possible forms was analyzed in terms of substituent effect stabilization energy (SESE). In the case of p-iminomethylphenylboronic acid, both hydroxyl groups are engaged in intermolecular O-H center dot center dot center dot O interactions resulting in a supramolecular ribbon motif. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.02.072
• 作为产物：
  描述：

  2-甲酰基苯硼酸 、 邻甲苯胺 以 二氯甲烷 为溶剂， 反应 9.5h， 以86%的产率得到2-(o-tolyliminomethyl)phenylboronic acid
  参考文献：
  名称：

  Imino- and aminomethylphenylboronic acids: stabilizing effect of hydrogen bonds

  摘要：

  ortho-Iminomethylphenylboronic acids were synthesized from the reaction of 2-formyl-phenylboronic acid with primary aromatic amines. Reduction of these compounds yielded the corresponding aminomethylphenylboronic acids. For both types of the compounds, the crystal structure was determined by single crystal X-ray diffraction method. Hydrogen-bonded dimers with an additional intramolecular B-O-H center dot center dot center dot N hydrogen bond have been observed. Calculations at MP2/6-31+G** level proved that the most stable form is that with the above-mentioned intramolecular hydrogen bond while the form with dative N -> B bond is less favoured. Since the calculated energy difference is small, the competition between possible forms was analyzed in terms of substituent effect stabilization energy (SESE). In the case of p-iminomethylphenylboronic acid, both hydroxyl groups are engaged in intermolecular O-H center dot center dot center dot O interactions resulting in a supramolecular ribbon motif. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.02.072

文献信息

• Imino- and aminomethylphenylboronic acids: stabilizing effect of hydrogen bonds
  作者：Agnieszka Adamczyk-Woźniak、Michał K. Cyrański、Beata T. Frączak、Agnieszka Lewandowska、Izabela D. Madura、Andrzej Sporzyński

  DOI：10.1016/j.tet.2012.02.072

  日期：2012.5

  ortho-Iminomethylphenylboronic acids were synthesized from the reaction of 2-formyl-phenylboronic acid with primary aromatic amines. Reduction of these compounds yielded the corresponding aminomethylphenylboronic acids. For both types of the compounds, the crystal structure was determined by single crystal X-ray diffraction method. Hydrogen-bonded dimers with an additional intramolecular B-O-H center dot center dot center dot N hydrogen bond have been observed. Calculations at MP2/6-31+G** level proved that the most stable form is that with the above-mentioned intramolecular hydrogen bond while the form with dative N -> B bond is less favoured. Since the calculated energy difference is small, the competition between possible forms was analyzed in terms of substituent effect stabilization energy (SESE). In the case of p-iminomethylphenylboronic acid, both hydroxyl groups are engaged in intermolecular O-H center dot center dot center dot O interactions resulting in a supramolecular ribbon motif. (C) 2012 Elsevier Ltd. All rights reserved.