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9-[(Z)-2-(4,4,5,5-Tetra-methyl-1,3,2-dioxaborolan-2-yl)ethen-yl]-9H-carbazole.

ABSTRACT: The title compound, C₂₀H₂₂BNO₂, has a polarized π-system due to resonance between N-C(H)=C(H)-B and ionic N⁺=C(H)-C(H)=B^- canonical structures. The dihedral angles between the ethenyl plane (r.m.s. deviation for C₂H₂ = 0.0333 Å) with the ethenyl-C(NC₂-pyrrole) plane (r.m.s. deviation CNC₂ 0.0423 Å) and the ethenyl-C(BO₂-1,3,2-dioxaborolane) plane (r.m.s. deviation BCO₂ 0.0082 Å) are 45.86 (8) and 37.47 (8)°, respectively, and are greater than those found for the previously reported E-isomer [Hatayama & Okuno (2012 ▸) Acta Cryst. E68, o84]. In comparison with the E-isomer, the reduced planarity of Z-isomer results in a decrease of the contribution of the N⁺=C(H)-C(H)=B^- canonical structure.

SUBMITTER: Kanagawa M

PROVIDER: S-EPMC9462315 | biostudies-literature | 2021 Feb

REPOSITORIES: biostudies-literature

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9-[(Z)-2-(4,4,5,5-Tetra-methyl-1,3,2-dioxaborolan-2-yl)ethen-yl]-9H-carbazole.

Kanagawa Mayu M Akagi Kazuto K Okuno Tsunehisa T

IUCrData 20210212 Pt 2

The title compound, C20H22BNO2, has a polarized π-system due to resonance between N-C(H)=C(H)-B and ionic N+=C(H)-C(H)=B- canonical structures. The dihedral angles between the ethenyl plane (r.m.s. deviation for C2H2 = 0.0333 Å) with the ethenyl-C(NC2-pyrrole) plane (r.m.s. deviation CNC2 0.0423 Å) and the ethenyl-C(BO2-1,3,2-dioxaborolane) plane (r.m.s. deviation BCO2 ...[more]

PMID: 36338862

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