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.1. Benzo Imidazole Salt Synthesis, Characterization And Quantum Chemical Calculations. Ferrocene Synthesis And Biological Activity Of Sulfonamide Derivatives Research

Posted on:2007-06-22Degree:MasterType:Thesis
Country:ChinaCandidate:J ZhangFull Text:PDF
GTID:2191360182995186Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
Cyanine dyes with benzimidazolium nucleus were widely used as sensitizers and other additives in the photographic industry, optical recording medium in laser disks, laser dyes, and optical sensitizers in various other fields. To synthesize 1,2,3-trimethlybenzimidazolium iodide which is the potential building block for the construction of cyanine dyes was widely regarded, because the configuration of cyanine dyes can be impoved by changing the structure of the potential building block 1,2,3-trimethlybenzimidazolium iodide.In this paper a novel benzimidazole derivative,l,3-dimethyl-2-ferrocenylmethylbenzimidazoliurn iodide, was synthesized. A new series of ferrocenyl-cyanine dye will be formed out by the reaction between this new intermediate and α,β-unsaturated aldehyde or ketone. Ferrocenyl is a good quencher group able to increase the stability of the cyanine dyes and hence the ferrocenyl-cyanine dye can be used more widely. The novel benzimidazole derivative, was characterized by elemental analysis, IR spectra, MS and ~1H NMR. Its crystal structure was determined by X-ray single crystal diffraction. According to the crystal structure, the quantum chemistry calculation was performed by Gaussian 03 program, and full geometry optimizations of the title compound were carried out with DFT method at B3LYP/631G level. Its structure, stability, net charge distribution and frontier molecular orbital components were discussed.The application of ferrocene and the derivatives have been attached the importance in many domains, especially in the field of medicine, biochemistry, fuel, catalyzer, because they have special biological activities, such as antitumor, antibacterial, antiviral activities, diminish inflammation, etc. Sulphanilamide derivatives is a kind of antibacterial and diminish inflammation medicine which have many merit. Now there are five thousands kinds of sulphanilamide derivatives had been synthesized. Many of them had been used widely in medicine. In this paper five new ferrocenesulfonyl amines derivatives were synthesized, and they are expected tohave special biological activities.Ferrocenesulfonyl amines derivatives were synthesized by method of microwave irradiation. Under the microwave irradiation, there are many benefits for organic reaction, such as short reaction time, high yield, less waste residue, easy purification, less pollution, which have won wide attention. As a result, microwave irradiation has been explored widely in organic synthesis. The Microwave Induced Organic Reaction Enhancement Chemistry is now found wide application and develops quickly, and the kinds of organic reaction that can be induced under microwave irradiation increase greatly. Green chemistry is a new strategy to prevent pollution from the beginning. It arose from organic chemistry, and organic synthesis is one of the key problems. Among the methods of realizing green synthesis, microwave dry reaction has been a hot point of organic synthesis. In this paper five new ferrocenesulfonyl amines derivatives were synthesized from ferrocenesulfonyl chloride and a-naphthylamine, (3-naphthylamine, piperazine, diphenylamine under the microwave irradiation. They were confirmed by elemental analysis, IR, MS and !H NMR, and the antimicrobial activity was tested in vitro against four pathogen.
Keywords/Search Tags:1,3-dimethyl-2-ferrocenylmethylbenzimidazolium, synthesis, crystal structure, quantum chemical calculation, ferrocenesulfonyl amines, microwave irradiation, antimicrobial activity
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