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
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author Hatayama, Yuki
Akagi, Kazuto
Okuno, Tsunehisa
author_facet Hatayama, Yuki
Akagi, Kazuto
Okuno, Tsunehisa
author_sort Hatayama, Yuki
collection PubMed
description 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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spelling pubmed-90285502022-11-04 N-Phenyl-N-[(E)-2-(4,4,5,5-tetra­methyl-1,3,2-dioxaborolan-2-yl)ethen­yl]aniline Hatayama, Yuki Akagi, Kazuto Okuno, Tsunehisa IUCrdata Data Reports 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] International Union of Crystallography 2022-01-28 /pmc/articles/PMC9028550/ /pubmed/36337091 http://dx.doi.org/10.1107/S2414314622000839 Text en © Hatayama et al. 2022 https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Data Reports
Hatayama, Yuki
Akagi, Kazuto
Okuno, Tsunehisa
N-Phenyl-N-[(E)-2-(4,4,5,5-tetra­methyl-1,3,2-dioxaborolan-2-yl)ethen­yl]aniline
title N-Phenyl-N-[(E)-2-(4,4,5,5-tetra­methyl-1,3,2-dioxaborolan-2-yl)ethen­yl]aniline
title_full N-Phenyl-N-[(E)-2-(4,4,5,5-tetra­methyl-1,3,2-dioxaborolan-2-yl)ethen­yl]aniline
title_fullStr N-Phenyl-N-[(E)-2-(4,4,5,5-tetra­methyl-1,3,2-dioxaborolan-2-yl)ethen­yl]aniline
title_full_unstemmed N-Phenyl-N-[(E)-2-(4,4,5,5-tetra­methyl-1,3,2-dioxaborolan-2-yl)ethen­yl]aniline
title_short N-Phenyl-N-[(E)-2-(4,4,5,5-tetra­methyl-1,3,2-dioxaborolan-2-yl)ethen­yl]aniline
title_sort n-phenyl-n-[(e)-2-(4,4,5,5-tetra­methyl-1,3,2-dioxaborolan-2-yl)ethen­yl]aniline
topic Data Reports
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9028550/
https://www.ncbi.nlm.nih.gov/pubmed/36337091
http://dx.doi.org/10.1107/S2414314622000839
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AT okunotsunehisa nphenylne24455tetramethyl132dioxaborolan2ylethenylaniline

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