5805-59-4Relevant articles and documents
(Benzimidazolylmethyl)amine ZnII and CuII carboxylate complexes: Structural, mechanistic and kinetic studies of polymerisation reactions of ε-caprolactone
Attandoh, Nelson W.,Ojwach, Stephen O.,Munro, Orde Q.
, p. 3053 - 3064 (2014)
Compounds N-(1H-benzimidazol-2-ylmethyl)aniline (L1), N-(1H-benzimidazol-2- ylmethyl)-2-bromoaniline (L2), and N-(1H-benzimidazol-2-ylmethyl)-2- aminothiophenol (L3) react with ZnII and CuII carboxylates to form complexes [Zn2(L1)2(OBn)4] (1), [Zn2(L2)2(OBn)4] (2), [Zn2(L3) 2(OBn)4] (3), [Cu2(L2)2(OBn) 4] (4), [Zn(L1)2(OAc)2] (5), [Zn(L2) 2(OAc)2] (6) and [Cu2(L1)2(OAc) 4] (7). Structures of 2, 4 and 6 revealed that L1-L3 are monodentate, binding through the imidazolyl N-atom. The X-band EPR spectrum of 4 in the solid state is consistent with an antiferromagnetically-coupled (singlet) ground state and a low-lying EPR-active triplet excited state characterised by two main transitions. In dimethyl sulfoxide (DMSO) solution, a single resonance confirmed the retention of the dinuclear paddlewheel core. Complexes 1-7 formed active catalysts towards ring-opening polymerisation of ε-caprolactone. The polymerisation reactions follow first-order kinetics with respect to the monomer and occur through a coordination-insertion pathway. Copyright
Light-activated cytotoxicity of dicarbonyl Ru(ii) complexes with a benzimidazole coligand towards breast cancer
Farag, Ahmad M.,Ibrahim, Nourhan M.,Khaled, Rabaa M.,Mansour, Ahmed M.,Radacki, Krzysztof,Ragheb, Mohamed A.
, p. 15389 - 15399 (2021/11/17)
Reaction between [RuCl2(CO)2]n and 1H-benzimidazol-2-ylmethyl-(N-phenyl)amine ligands (LR) functionalized with various electron-donating and electron-withdrawing substituents on the phenyl ring (R = H, 4-CH3, 4-Cl, 4-COOCH3, and 3-COOCH3) afforded the dark-stable photoactivatable carbon monoxide prodrugs of the general formula [RuCl2(CO)2LR]. Release of the CO molecules from the Ru(ii) compounds was examined by monitoring the electronic and IR spectra upon illumination at 365 nm. A noticeable decrease in the intensities of the two characteristic ν(CO) modes for Ru(CO)II2 species, and the growth of two new bands for the mono-carbonyl species and free CO, were the main features of the photolysis profiles. The cytotoxicity of the complexes towards breast cancer (MCF-7) cells was assessed with and without illumination at 365 nm. All the complexes except that with a 4-COOCH3 group (IC50 = 45.08 ± 3.5 μM) are nontoxic under dark conditions. Upon illumination, all the compounds acquired cytotoxicity in the following order: H > 4-COOCH3 > 4-CH3 > 4-Cl > 3-COOCH3. Investigation of the cytotoxicity of the CO-depleted fragments showed that the light-induced cytotoxicity can be attributed to the liberated CO and CO-depleted metal fragments, including the liberated benzimidazole ligands.
Cooperative Mn(i)-complex catalyzed transfer hydrogenation of ketones and imines
Ganguli, Kasturi,Shee, Sujan,Panja, Dibyajyoti,Kundu, Sabuj
, p. 7358 - 7366 (2019/06/06)
The synthesis and reactivity of Mn(i) complexes bearing bifunctional ligands comprising both the amine N-H and benzimidazole fragments are reported. Among the various ligands, the N-((1H-benzimidazol-2-yl)methyl)aniline ligand containing Mn(i) complex presented higher reactivity in the transfer hydrogenation (TH) of ketones in 2-propanol. Experimentally, it was established that both the benzimidazole and amine N-H proton played a vital role in the enhancement of the catalytic activity. Utilizing this system a wide range of aldehydes and ketones were reduced efficiently. Notably, the TH of several imines, as well as chemoselective reduction of unsaturated ketones, was achieved in the presence of this catalyst. DFT calculations were carried out to understand the plausible reaction mechanism which disclosed that the transfer hydrogenation reaction followed a concerted outer-sphere mechanism.
