Hatayama Yuki, Akagi Kazuto, Okuno Tsunehisa
Department of Systems Engineering, Wakayama University, Sakaedani, Wakayama, 640-8510, Japan.
IUCrdata. 2022 Jan 28;7(Pt 1):x220083. doi: 10.1107/S2414314622000839. eCollection 2022 Jan.
The title compound, CHBNO, 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 NCB plane (r.m.s. deviation 0.0223 Å) and the CN (r.m.s. deviation 0.0025 Å) and BCO (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 orbital of the boron atom are conjugated with the central C=C bond. In comparison with the carbazole analogue [Hatayama & Okuno (2012 ▸). E, 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.
标题化合物CHBNO具有极化的π体系,这是由于N-C(H)=C(H)-B与离子型N=C(H)-C(H)=B标准形式之间存在显著共振。NCB平面(均方根偏差0.0223 Å)与CN平面(均方根偏差0.0025 Å)和BCO平面(均方根偏差0.0044 Å)之间的二面角分别为2.51 (12)°和3.09 (19)°。这表明氮原子的孤对电子和硼原子的一个空轨道与中心C=C键共轭。与咔唑类似物[Hatayama & Okuno (2012 ▸). E, o84]相比,C-N键和C-B键更短。通过标题化合物中N=C(H)-C(H)=B标准形式贡献的增加,可以很好地解释这些结果。