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9-[(Z)-2-(4,4,5,5-Tetra-methyl-1,3,2-dioxaborolan-2-yl)ethen-yl]-9H-carbazole
Mayu Kanagawa1, Kazuto Akagi1, Tsunehisa Okuno1
1Department of Systems Engineering, Wakayama University, Sakaedani, Wakayama, 640-8510, Japan.
This study analyzes a Z-isomer compound, revealing its polarized pi-system and non-planar structure. Compared to the E-isomer, its reduced planarity impacts electronic resonance structures.
Area of Science:
- Organic Chemistry
- Crystallography
- Computational Chemistry
Background:
- The title compound, C20H22BNO2, exhibits a polarized pi-system.
- Resonance occurs between neutral and ionic canonical structures, influencing electronic properties.
Purpose of the Study:
- To characterize the structural and electronic properties of the Z-isomer.
- To compare its planarity and resonance contribution with the previously reported E-isomer.
Main Methods:
- Analysis of dihedral angles using crystallographic data.
- Evaluation of canonical structure contributions based on molecular geometry.
Main Results:
- The Z-isomer displays significant dihedral angles (45.86° and 37.47°) between its ethenyl and substituent planes.
- These angles indicate reduced planarity compared to the E-isomer.
- Reduced planarity leads to a diminished contribution of the ionic N+=C(H)-C(H)=B- canonical structure.
Conclusions:
- The Z-isomer's non-planar geometry affects its electronic delocalization.
- Structural differences between Z and E isomers significantly alter their electronic characteristics.
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