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Updated: Aug 23, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
N-Phenyl-N-[(E)-2-(4,4,5,5-tetra-methyl-1,3,2-dioxaborolan-2-yl)ethen-yl]aniline.
Yuki Hatayama1, Kazuto Akagi1, Tsunehisa Okuno1
1Department of Systems Engineering, Wakayama University, Sakaedani, Wakayama, 640-8510, Japan.
This study reveals a polarized π-system in a novel boron-nitrogen compound. Increased resonance in its ionic form leads to shorter C-N and C-B bonds compared to analogues.
Area of Science:
- Organic Chemistry
- Crystallography
- Computational Chemistry
Background:
- The compound C20H24BNO2 exhibits a unique electronic structure.
- Understanding π-system polarization is crucial in novel material design.
Purpose of the Study:
- To investigate the electronic properties and structural characteristics of the title compound.
- To analyze the resonance contributions affecting its chemical bonds.
Main Methods:
- X-ray crystallography was employed to determine the molecular structure.
- Analysis of canonical forms and dihedral angles elucidated electronic conjugation.
Main Results:
- A polarized π-system was identified, driven by resonance between neutral and ionic forms.
- Shortened C-N and C-B bonds were observed compared to carbazole analogues.
- Dihedral angles indicated significant conjugation between nitrogen's lone pair, boron's vacant p orbital, and the central C=C bond.
Conclusions:
- The electronic structure is significantly influenced by the ionic N+=C(H)-C(H)=B- canonical form.
- This resonance stabilization explains the observed bond shortening and planarity.
- The findings offer insights into the design of novel π-conjugated systems.
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