62366-40-9Relevant academic research and scientific papers
Photochemical synthesis of a palladium dichloromethyl complex, {(hexyl)HC(N-methyl-imidazol-2-yl)2}Pd(CHCl2)Cl. X-ray molecular structures of {(hexyl)HC(N-methylimidazolyl-2-yl)2} Pd(X)Cl, X=Cl, and CHCl2
Burns, Christopher T.,Shen, Han,Jordan, Richard F.
, p. 240 - 248 (2003)
The reaction of (hexyl)HC(mim)2 (1, mim= N -methyl-imidazol-2-yl) with (cod)PdMeCl in C6H6 yields {(hexyl)HC(mim)2}Pd(Me)Cl (3). The photochemical reaction of 3 with CH2Cl2 at 23 °C in ambient room light yields {(hexyl)HC(mim)2}Pd(CHCl2)Cl (4). It is proposed that this reaction proceeds by homolytic scission of the Pd-Me bond of 3.
From bis(Imidazol-2-yl)methanes to asymmetrically substituted bis(heterocyclo)methanides in metal coordination
Dauer, David-R.,Koehne, Ingo,Herbst-Irmer, Regine,Stalke, Dietmar
, p. 1966 - 1978 (2017)
As an extension to the known symmetric bis(heterocyclmethanes containing two identical heterocycles, new asymmetric ligand systems, based on benzoxazole, benzothiazole and 1-methylbenzimidazole, are presented. Furthermore, the syntheses and reactions of two new symmetrically substituted methane derivatives, containing either 1-methylimidazole or 1-methylbenzimidazole, are discussed. In this context, firstly, (1-MeNCNC2H2)2CH2 and (1-MeNCNC6H4)2CH2, and secondly, (NCSC6H4)CH2(NCOC6H4) and (NCSC6H4)CH2(1-MeNCNC6H4), are used as parent compounds. They can be easily deprotonated at the central methylene bridge to generate a monoanionic structure akin to NacNac, so that the following complexes can be obtained: [Me2Al{(1-MeNCNC2H2)2CH}], [Me2Al{(1-MeNCNC6H4)2-CH}], [Me2Al{(NCSC6H4)CH(NCOC6H4)}], [Me2Ga{(NCSC6H4)CH-(NCOC6H4)}], [Me2Al{(NCSC6H4)CH(1-MeNCNC6H4)}],[(THF)2Li{(1-MeNCNC6H4)2CH}] and [(diox)2Li{(NCSC6H4)CH(1-MeNCNC6H4)}]. These compounds have been fully characterised by single-crystal X-ray diffraction (in the solid statand NMR spectroscopy (in solution).
Transition metal complexes of the novel hexadentate ligand 1,4-bis(di(N-methylimidazol-2-yl)methyl)phthalazine
Roggan, Stefan,Limberg, Christian,Knispel, Christina,Tilley, T. Don
, p. 4315 - 4323 (2011)
The novel polydentate ligand 1,4-bis(di(N-methylimidazol-2-yl)methyl) phthalazine, bimptz, has been synthesized and its coordination chemistry was investigated. Bimptz is neutral and contains a central phthalazine unit, to which two di-(N-methylimidazol-2-yl)methyl groups are attached in the 1,4-positions. This ligand therefore provides up to 6 donor sites for coordination to metal ions. A series of metal complexes of bimptz was prepared and their molecular structures were determined by X-ray diffraction. Upon reaction of bimptz with two equivalents of MnCl2·4H 2O, CoCl2·6H2O and [Ru(dmso) 4Cl2], the dinuclear complexes [Mn2(bimptz)(- Cl)2Cl2] (1), [Co2(bimptz)(CH 3OH)2(-Cl)2](PF6)2 (3) and [Ru2(bimptz)(dmso)2(-Cl)2](PF 6)2 (4), respectively, were isolated. The latter were found to have similar solid state structures with octahedrally coordinated metal centers bridged by the phthalazine unit and two chloro ligands. The cobalt and ruthenium complexes 3 and 4 were isolated as PF6- salts and contain neutral methanol and dmso ligands, respectively, at the terminal coordination sites of the metal centres. The mononuclear ruthenium complex [Ru(Hbimptz)2](PF6)4 (6) was obtained from the reaction of two equivalents bimptz with [Ru(dmso)4Cl2]. In complex 6, three donor sites per ligand molecule are used for coordination of the Ru(ii) center. In each bimptz ligand, one of the remaining, dangling N-methylimidazole rings is protonated and forms a hydrogen bond with the unprotonated N-methylimidazole ring of the other bimptz ligand.
Bridged 1-methylbisimidazoles as building blocks for mixed donor bi- and tridentate chelating ligands
Braussaud,Rüther,Cavell,Skelton,White
, p. 626 - 632 (2007/10/03)
Novel bi- and tridentate imidazole chelate ligands consisting of varying donor sets were prepared using an efficient one- or two-step procedure. Keto- and methylene-bridged bisimidazoles 1, 2 served as versatile starting materials for the introduction of additional donor groups, thus allowing the facile variation of donor sets within a bisimidazole ligand framework.
Expedient synthesis of symmetric aryl ketones and of ambient-temperature molten salts of imidazole
Lucas,El Mehdi,Ho,Belanger,Breau
, p. 1253 - 1258 (2007/10/03)
A short procedure for the synthesis of 2,2-di(3-thienyl)-1,3-dioxolan is described. The route developed is convenient (only two synthetic and one chromatographic steps are required) and efficient (66% overall yield from 3-bromothiophene). This compound was transformed into the ketone, cyclopenta[2,1-b:3',4'-b']dithiophen-4-one by a known process. Optimized syntheses of symmetric aryl ketones, 1-alkyl-3-methylimidazolium and 1-alkyl-2-methyl-3-methylimidazolium liquid salts are also reported.
Efficient Synthesis of a Porphyrin - N-Tripod Conjugate with Covalently Linked Proximal Ligand: Toward New-Generation Active-Site Models of Cytochrome c Oxidase
Collman, James P.,Zhong, Min,Wang, Zhong,Rapta, Miroslav,Rose, Eric
, p. 2121 - 2124 (2008/02/09)
Matrix Presented A new-generation cytochrome c oxidase active-site model compound (4) featuring both a trisimidazolyl moiety and a proximal base has been designed and efficiently synthesized. During this study, a facile method based on the chemistry of a
Synthesis of Novel Ruthenium Complexes Containing Bidentate Imidazole-based Ligands
Elgafi, Sarah,Field, Leslie D.,Messerle, Barbara A.,Hambley, Trevor W.,Turner, Peter
, p. 2341 - 2346 (2007/10/03)
Ruthenium(II) complexes containing the bidentate imidazole-based ligands (MeN2H2C3)2CO L1, (MeN2H2C3)2CHOH L2 and (MeN2H2C3)2CH2 L3 (where 1-MeN2H2C3 = 1-methylimidazol-2-yl), 1>Cl 1, 2>Cl 2 and 3>Cl 3, were synthesized by the reaction of L1-L3 with in toluene.The complexes were characterised by NMR spectroscopy and the crystal structures of 1>BF4 4 and 2>OH 5 determined.
2-Protecting Groups for 5-Lithiation in the Synthesis of Imidazoles
Ngochindo, Raphael I.
, p. 1645 - 1648 (2007/10/02)
Various substituents have been examined as possible 2-protecting groups against organolithium reagents in the syntheses of imidazoles on the basis of the ease of decarboxylation of imidazole-2-carboxylic acids and cleavage of the C(2)-Si bond.The tertiary
Synthesis, Structure, and Magnetic and Moessbauer Properties of Mononuclear and Asymmetric, Oxo-Bridged Trinuclear Iron(III) Complexes of a New Polyimidazole Ligand.
Gorun, Sergiu M.,Papaefthymiou, Georgia C.,Frankel, Richard B.,Lippard, Stephen J.
, p. 4244 - 4255 (2007/10/02)
The synthesis of 1,1,2-tris(N-methylimidazol-2-yl)-1-hydroxyethane (TIEOH) is described.Reaction of TIEOH with Fe(ClO4)3*10H2O yields upon workup and crystallization, the high-spin, pseudooctahedral iron(III) monomer (ClO4)2, in which two imidazole ring nitrogen atoms and an alkoxide oxygen atom both TIEO- and HTIEO ligands are coordinated to the metal.The dangling imidazole of the HTIEO ligand is protonated, as revealed in an X-ray crystal structure determination.Two procedures are described for preparing the novel trinuclear complex *2C6H6.This trinuclear complex slowly decomposes in solution to form 2+, where BIK is bis(N-methylimidazol-2-yl) ketone.An X-ray crystallographic study of the trinuclear complex revealed an isosceles triangle of iron atoms with a triply bridging oxo atom nearly in the plane of the triangle.The structure of the 7+ core consists of two short Fe-O bonds and one long one .The coordination spheres of the equivalent iron atoms, Fe1 and Fe2, are each composed of two imidazole nitrogen atoms, the bridging oxo atom, a bridging alkoxide oxygen atom of the TIEO- ligand, an oxygen atom of a bridging benzoate ligand, and a terminal chloride ion.The two benzoate, two alkoxide and μ-oxo groups bridge to Fe3, which has a terminal chloride ligand to complete its coordination sphere.Two N-methylimidazole groups, one from each ligand, are not coordinated.From magnetization studies the ground state of is found to be ST = 5/2, in contrast to the classical basic iron(III) carboxylates, which contain symmetrically bridged 7+ cores having ST = 1/2.Variable-temperature magnetic susceptibility measurements were fit to a theoretical expression derived from a spin Hamiltonian taking into account two different exchange pathways along inequivalent sides of the isosceles triangle.The analysis yielded J12= -55(1) cm-1 and J13 = J23 = -8.0(4) cm-1, with the large antiferromagnetic coupling interaction occuring between iron centers linked by the shortest μ-oxo bridge bonds.Moessbauer isomer shift and quadrupole splitting parameters at 4.2 K are δ 0.48 and 0.52 mm/s and ΔEQ = 1.16 and 0.74 mm/s for Fe1 (=Fe2) and Fe3, respectively.In external magnetic fields at 4.2 K there are two magnetic subsites with Hhf(1) = Hhf(2) = 0 and Hhf(3) = -540 kOe, corresponding to Fe1 and Fe2 with local spin z> = 0 and Fe3 with local spin z = 5/2.This result confirms the T = 5/2, Sp = 0> ground state of the cluster.Electronic, vibrational, and NMR spectra are also briefly reported.These results are compared and contrasted with structural, magnetic, and spectroscopic data for (μ-oxo)diiron(III), (μ-hydroxy)diiron(III), and symmetric (μ3-oxo)triiron(III)cores which, unlike the present asymmetric (μ3-oxo)triiron(III) core, are ubiquitous in ...
Synthesis of Ketones and Methanols Containing Pyridinyl and N-Methylimidazolyl Groups
Canty, Allan J.,George, Edwin E.,Lee, Christopher V.
, p. 415 - 418 (2007/10/02)
N-Methylimidazolyllithium reacts with N-methylimidazole-2-carboxaldehyde to form bis(N-methylimidazol-2-yl)methanol, and with the esters ethyl N-methylimidazole-2-carboxylate and ethyl pyridine-2-carboxylate to give bis(N-methylimidazol-2-yl)methanone, (mim)2CO, and (N-methylimidazol-2-yl)(pyridin-2-yl)methanone, (Py)(mim)CO, respectively.The ketones react with N-methylimidazolyllithium to give tris(N-methylimidazol-2-yl)methanol, (mim)3COH, and bis(N-methylimidazol-2-yl)(pyridin-2-yl)methanol, (Py)(mim)2COH, respectively.
