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. 2022 Jan 28;7(Pt 1):x220083.
doi: 10.1107/S2414314622000839. eCollection 2022 Jan.

N-Phenyl- N-[(E)-2-(4,4,5,5-tetra-methyl-1,3,2-dioxaborolan-2-yl)ethen-yl]aniline

Yuki Hatayama  1 , Kazuto Akagi  1 , Tsunehisa Okuno  1
Affiliations

N-Phenyl- N-[(E)-2-(4,4,5,5-tetra-methyl-1,3,2-dioxaborolan-2-yl)ethen-yl]aniline

Yuki Hatayama et al. IUCrdata. .

Abstract

The title compound, C20H24BNO2, has a polarized π-system due to significant resonance between the N-C(H)=C(H)-B and ionic N+=C(H)-C(H)=B- canonical forms. The dihedral angles between the NC2B plane (r.m.s. deviation 0.0223 Å) and the C3N (r.m.s. deviation 0.0025 Å) and BCO2 (r.m.s. deviation 0.0044 Å) planes are 2.51 (12) and 3.09 (19)°, respectively. This indicates the lone pair of the nitro-gen atom and a vacant p orbital of the boron atom are conjugated with the central C=C bond. In comparison with the carbazole analogue [Hatayama & Okuno (2012 ▸). Acta Cryst. E68, o84], the C-N and C-B bonds are shorter. The results are well explained by the increase in the contribution of the N+=C(H)-C(H)=B- canonical form in the title compound.

Keywords: crystal structure; dioxaborolan-2-yl; resonance.

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Figures

Figure 1
Figure 1
The mol­ecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level; H are atoms shown as small spheres.
See this image and copyright information in PMC

References

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    1. Onuma, K., Suzuki, K. & Yamashita, M. (2015). Chem. Lett. 44, 405–407.
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