N-Phenyl-N-[(E)-2-(4,4,5,5-tetra­methyl-1,3,2-dioxaborolan-2-yl)ethen­yl]aniline

The title compound, C(20)H(24)BNO(2), 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 NC(2)B plane (r.m.s. deviation 0.0223 Å) and the C(3)N (r.m.s. deviation 0.0025 Å) and BCO(2) (r.m.s. d...

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Detalles Bibliográficos
Autores principales: Hatayama, Yuki, Akagi, Kazuto, Okuno, Tsunehisa
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2022
Materias:
Data Reports
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9028550/
https://www.ncbi.nlm.nih.gov/pubmed/36337091
http://dx.doi.org/10.1107/S2414314622000839
Descripción
Sumario:The title compound, C(20)H(24)BNO(2), 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 NC(2)B plane (r.m.s. deviation 0.0223 Å) and the C(3)N (r.m.s. deviation 0.0025 Å) and BCO(2) (r.m.s. deviation 0.0044 Å) planes are 2.51 (12) and 3.09 (19)°, respectively. This indicates the lone pair of the nitro­gen 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. [Image: see text]

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