Synthesis and characterization of bulky salen-type complexes of Co, Cu, Fe, Mn and Ni with amphiphilic solubility properties

Haikarainen, Anssi; Sipilä, Jussi; Pietikäinen, Pirjo; Pajunen, A.; Mutikainen, Ilpo

doi:10.1039/b008167l

Cited by 71 publications

(33 citation statements)

References 18 publications

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“…General procedure for the preparation of salen ligands 1 A-F (Scheme 1): K 2 CO 3 (0.5 mmol) in water (2 mL) was added to a solution of salicylaldehyde (0.5 mmol) and (1R,2R)-1,2-cyclohexanediammonium monotartrate (0.25 mmol) in ethanol (10 mL). The re- 134.8, 134.1, 134.0, 133.5, 133.4, 132.4, 132.1, 131.7, 130.0, 129.9, 129.7, 129.6, 128.5, 128.3, 118.4, 118.0, 117.1, 114.8, 71.0, 34.4, 32.5, 30.2, 29.4, 28.9 General procedure for the synthesis of the bifunctional metal complex catalysts: [16,[21][22][23] The metal salt ( 2 ; 0.1 mmol) and the ligand (0.1 mmol) were dissolved in methanol (6 mL) under argon. The reaction mixture was heated at reflux for 2 h. The solvent was evaporated to yield the metal complex.…”

Section: Discussionmentioning

confidence: 99%

Bifunctional Chiral Catalyst for the Synthesis of Chiral Cyclic Carbonates from Carbon Dioxide and Epoxides

2009

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Bifunctional chiral catalysts incorporating the N,N′‐bis(salicylidene)cyclohexenediaminato (salen) ligand and a quaternary onium salt within one metal complex were synthesized and developed for the catalytic kinetic resolution of racemic epoxides with carbon dioxide to generate chiral cyclic carbonates in high yield and with moderate enantioselectivity. These new catalysts also have a great advantage as they can be recycled without any obvious loss of activity and enantioselectivity.

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Section: Discussionmentioning

confidence: 99%

Bifunctional Chiral Catalyst for the Synthesis of Chiral Cyclic Carbonates from Carbon Dioxide and Epoxides

2009

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“…With the lone-pair electron afforded by the basic structure of C＝ N structure, salen complexes have been of interest for their bioactivity, 1,2 and can identify both imidazole, pyridine, amino acids and other nitrogen-containing small molecules and complex molecular system such as carbohydrates, DNA molecules. [3][4][5] Most notably, they have been found to be of great utility in the development of chiral catalysts, and have been used to increase the stereoselectivity of products in a variety of reactions including asymmetric nitroaldol reaction, 6,7 asymmetric epoxidation, [8][9][10] ring-opening of epoxides, and so on. Under the background of energy conservation, security and green chemistry, the efficient and recyclable catalyst of salen type becomes an on-going research focus.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of a Series of New Asymmetric Salphen Mono‐ and Binuclear Metal Complexes

Guo

Ruan

et al. 2010

Chin. J. Chem.

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“…The H2salen (N,N'-bis(salicylidene)ethane-1,2-diamine) that used as a ligand was prepared from salicylaldehyde and ethylenediamine by the reported method (Haikarainen, Sibila, Pietikainen, Pajunen, & Mutikainen, 2001). The dark brown crystals of the [Mn(salen)OAc] complex were obtained in 45-67% yield.…”

Section: Synthesis Of [Mn(salen)oac] Complexmentioning

confidence: 99%

Activity of Superoxide Dismutase Mimic of [Mn(salen)OAc] Complex Compound Non-enzymatically in Vitro Through Riboflavin Photoreduction

Deawati

Onggo

Mulyani

et al. 2017

Molekul

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The complex compound of [Mn(salen)OAc] can serve as mSOD and its activity has been determined nonenzymatically in vitro through riboflavin photoreduction. The complex was synthesized from Mn(OAc)2.4H2O and H2salen. Based on the elemental analysis, the C=56.69%; H=4.21%; and N=7.52% content are corresponding to the chemical formula of MnC18H17N2O4. The functional groups and ionic species in the complex have been analyzed by infrared spectroscopy and ESI-MS. SOD activity was determined by mixing complex at various concentrations with riboflavin and nitroblue tetrazolium (NBT), then the mixture was lighted with 20 watts tungsten lamp for 15 minutes in a closed box. Then the reduced NBT absorptions were measured at λ 560 nm. The difference of absorbance between standard and sample solutions (without and with riboflavin, respectively) was multiplied by 100% to obtain %inhibition of each various sample concentration against NBT. SOD activity was obtained from IC50 data defined as a 50% inhibition of the plot curve of % inhibition to the concentration of the complex. The result obtained for this compound is IC50 = 2.7 ± 0.1 µM as well as enzymatic method. Therefore, this method can be used to determine the SOD activity by giving more stability and accuracy of IC50 value.Keywords: [Mn(salen)OAc], SOD, non-enzymatic, photoreduction, riboflavin ABSTRAK Senyawa kompleks [Mn(salen)OAc] dapat berfungsi sebagai mSOD dan aktivitasnya telah ditentukan secara in vitro non-enzimatik melalui fotoreduksi riboflavin. Kompleks ini disintesis dari Mn(OAc)2.4H2O dan H2salen. Berdasarkan analisis unsur diperoleh kadar unsur C=56,69%; H=4,21%; dan N=7,52% yang sesuai dengan rumus kimia MnC18H17N2O4. Gugus fungsi dan spesi ion dalam kompleks tersebut telah dianalisis dengan spektroskopi inframerah dan ESI-MS. Aktivitas SOD ditentukan dengan mencampurkan kompleks pada berbagai konsentrasi dengan riboflavin dan nitroblutetrazolium (NBT), yang kemudian campuran tersebut disinari oleh lampu wolfram 20 watt selama 15 menit pada kotak tertutup. Setelah itu serapan NBT tereduksi diukur pada λ 560 nm. Perbedaan absorbansi antara larutan standar dan sampel (masing-masing tanpa dan dengan adanya riboflavin) dikalikan dengan 100% untuk mendapatkan % inhibisi dari setiap variasi konsentrasi sampel terhadap NBT. Aktivitas SOD diperoleh dari data IC50 yang ditentukan sebagai 50% inhibisi pada kurva aluran persen inhibisi terhadap konsentrasi kompleks. Hasil yang diperoleh untuk kompleks ini adalah IC50 = 2,7 ± 0,1 µM sama seperti pada metode enzimatik. Oleh karena itu metode ini dapat digunakan untuk menentukan aktivitas SOD dengan memberikan nilai IC50 yang lebih stabil dan akurat.

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Synthesis and characterization of bulky salen-type complexes of Co, Cu, Fe, Mn and Ni with amphiphilic solubility properties

Cited by 71 publications

References 18 publications

Bifunctional Chiral Catalyst for the Synthesis of Chiral Cyclic Carbonates from Carbon Dioxide and Epoxides

Bifunctional Chiral Catalyst for the Synthesis of Chiral Cyclic Carbonates from Carbon Dioxide and Epoxides

Synthesis and Characterization of a Series of New Asymmetric Salphen Mono‐ and Binuclear Metal Complexes

Activity of Superoxide Dismutase Mimic of [Mn(salen)OAc] Complex Compound Non-enzymatically in Vitro Through Riboflavin Photoreduction

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