COA of Formula: C21H24N2. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene, is researched, Molecular C21H24N2, CAS is 141556-42-5, about NHC-Stabilized 1,2-Dihalodiborenes: Synthesis, Characterization, and Reactivity Toward Elemental Chalcogens. Author is Stoy, Andreas; Arrowsmith, Merle; Eysselein, Maximilian; Dellermann, Theresa; Mies, Jan; Radacki, Krzysztof; Kupfer, Thomas; Braunschweig, Holger.
The 2-fold reduction of B2X4(NHC)2 (X = Cl, Br, I; NHC = (un)saturated N-heterocyclic carbene) yields the corresponding green-colored 1,2-dihalodiborenes B2X2(NHC)2, the 11B NMR resonances of which are strongly upfield-shifted upon descending the halide group. The diborenes crystallize as the trans isomers, with relatively short B=B double bonds (1.513(9) to 1.568(4) Å). Cyclic voltammetric experiments with these diborenes reveal reversible one-electron oxidation processes to the corresponding diboron radical cation (E1/2 = -1.16 to -1.50 V); the reducing power of B2X2(NHC)2 increasing with the electronegativity of the halide and for the less π-accepting unsaturated NHCs. The main UV-vis absorption (393-463 nm), which corresponds mainly to a HOMO → LUMO transition, undergoes a blue shift upon descending the halide group and shows some dependence on the stereoelectronics of the NHC ligands. Computational analyses show that the HOMO of B2X2(NHC)2 is mostly localized on the B=B π bond, with the contribution from halide p orbitals decreasing down the group, and the saturated NHCs affording some π-bonding delocalization over the B-CNHC bonds. The calculated HOMO and LUMO energies decrease upon descending the halide group, while the HOMO-LUMO gap also decreases, correlating well with the cyclovoltammetry and UV-vis data. The reactions of B2Br2(NHC)2 with elemental sulfur and red selenium lead to the formation of the corresponding diborathiiranes and seleniranes, resp., which were characterized by NMR and UV-vis spectroscopy, cyclic voltammetry, and X-ray diffraction analyses. In one case, an addnl. one-electron oxidation yields a unique cyclic B2Se radical cation. Computational analyses show that the localization of the HOMO and HOMO – 1 of the diboraseleniranes is inverted compared to the diborathiiranes.
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