Tricyanoborane-Functionalized Anionic N-Heterocyclic Carbenes: Adjustment of Charge and Stereo-Electronic Properties.

ABSTRACT: The 1-methyl-3-(tricyanoborane)imidazolin-2-ylidenate anion (2) was obtained in high yield by deprotonation of the B(CN)₃ -methylimidazole adduct 1. Regarding charge and stereo-electronic properties, anion 2 closes the gap between well-known neutral NHCs and the ditopic dianionic NHC, the 1,3-bis(tricyanoborane)imidazolin-2-ylidenate dianion (IIb). The influence of the number of N-bonded tricyanoborane moieties on the σ-donating and π-accepting properties of NHCs was assessed by quantum chemical calculations and verified by experimental data on 2, IIb, and 1,3-dimethylimidazolin-2-ylidene (IMe, IIa). Therefore NHC 2, which acts as a ditopic ligand via the carbene center and the cyano groups, was reacted with alkyl iodides, selenium, and [Ni(CO)₄ ] yielding alkylated i

SUBMITTER: Zapf L 

PROVIDER: S-EPMC9401011 | biostudies-literature | 2022 Jul

REPOSITORIES: biostudies-literature