Evidence of Reversible N-H Exchange in a Three-Coordinate Amidozinc Complex. Syntheses and Structures of 1-Methyl-2-((N-tert-butylamino)methyl)benzimidazole Complexes of Zinc was written by Chinn, Mitchell S.;Chen, Jiazhong. And the article was included in Inorganic Chemistry in 1995.Quality Control of 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde This article mentions the following:
1-Methyl-2-((N-tert-butylamino)methyl)benzimidazole (HL) reacts with 1 equiv of Zn[N(SiMe3)2]2 in nonpolar solvents (benzene, toluene) yielding planar, 3-coordinate [ZnL(N(SiMe3)2)] (3) and HN(SiMe3)2. Compound 3 was characterized by 1H and 13C NMR spectroscopy, elemental anal., and x-ray crystallog. The crystal structure of this complex at -100° (monoclinic, space group P21/n, a 8.468(2), b 18.700(4), c 15.551(2) Å, β 98.10(2)°, Z = 4, R = 4.43%, Rw = 5.35%) shows two short, equivalent amidozinc bonds of 1.874(4) Å and 1.887(4) Å and a longer Zn-N coordinate covalent bond of 2.067(4) Å to the benzimidazole N atom. No evidence of Zn–:N+ double bond character is found even though a N lone pair and an empty, p-like Zn orbital are geometrically arranged for favorable overlap. Magnetization transfer studies show reversible, degenerate exchange between 3 and HL at 40°. Compound 3 undergoes rapid, irreversible protonolysis with HNMe2 to produce HL, HN(SiMe3)2, and a white precipitate Addition of HL to a Et2O solution of ZnCl2 immediately forms a white precipitate of [ZnLCl2] (2). Single crystals of 2 were grown from CH2Cl2 solutions The mol. structure of 2, determined by x-ray crystallog. at -100° (monoclinic, space group P21/n, a 7.622(2), b 14.378(3) Å, c 14.476(3) Å, β 104.91(2)°, Z = 4, R = 3.14%, Rw = 3.61%), shows the Zn atom in a distorted tetrahedral environment. Bonding between Zn and N atoms in four-coordinate 2 and three-coordinate 3 is compared. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4Quality Control of 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde).
1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4) belongs to imidazole derivatives. Imidazole is the basic core of some natural products such as histidine, purine, histamine and DNA based structures, etc. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Quality Control of 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde
Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem