- Physico-chemical properties of N,N-di(2-hydroxyethyl)alkylamines
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In view of potential application of N-alkyl derivatives of diethanolamine RN(CH2CH2OH)2 (R = C8H17, C10H21, C12H25, and C 14H29) as su
- Nasrtdinova,Koltashev,Radushev,Chekanova
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- Synthesis, Characterization, and Catalytic Reactivity of {CoNO}8PCP Pincer Complexes
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The reaction of coordinatively unsaturated Co(II) PCP pincer complexes with nitric oxide leads to the formation of new, air-stable, diamagnetic mono nitrosyl compounds. The synthesis and characterization of five- and four-coordinate Co(III) and Co(I) nitrosyl pincer complexes based on three different ligand scaffolds is described. Passing NO through a solution of [Co(PCPNMe-iPr)Cl], [Co(PCPO-iPr)Cl] or [Co(PCPCH2-iPr)Br] led to the formation of the low-spin complex [Co(PCP-iPr)(NO)X] with a strongly bent NO ligand. Treatment of the latter species with (X = Cl, Br) AgBF4 led to chloride abstraction and formation of cationic square-planar Co(I) complexes of the type [Co(PCP-iPr)(NO)]+ featuring a linear NO group. This reaction could be viewed as a formal two electron reduction of the metal center by the NO radical from Co(III) to Co(I), if NO is counted as NO+. Hence, these systems can be described as {CoNO}8 according to the Enemark-Feltham convention. X-ray structures, spectroscopic and electrochemical data of all nitrosyl complexes are presented. Preliminary studies show that [Co(PCPNMe-iPr)(NO)]+ catalyzes efficiently the reductive hydroboration of nitriles with pinacolborane (HBpin) forming an intermediate {CoNO}8 hydride species.
- Pecak, Jan,Eder, Wolfgang,St?ger, Berthold,Realista, Sara,Martinho, Paulo N.,Calhorda, Maria José,Linert, Wolfgang,Kirchner, Karl
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p. 2594 - 2601
(2020/06/22)
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- Synthesis, Characterization, Surface, and Thermodynamic Studies of Alkyl Tetrachloroferrates: Performance Evaluation of Their Nanostructures as Biocides
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Decyl and dodecylamino tetrachloroferrates were synthesized and characterized using Fourier-transform infrared spectroscopy (FTIR), elemental analysis, X-ray diffraction (XRD), nuclear magnetic resonance (1H-NMR), and atomic absorption spectroscopy (AAS). The surface properties of the cationic surfactants including critical micelle concentration, effectiveness, minimum surface area, and maximum surface excess were determined using surface tension measurements. The effectiveness of surface tension reduction (πcmc) was found to increase as the hydrophobic chain length increases with values of 30 and 34 mN m?1 for C10 and C12, respectively. Moreover, the effect of temperature on micellization was determined over the range of 35–55?°C. Thermodynamic parameters (ΔG°, ΔS°, and ΔH°) were calculated and the results indicate a spontaneous process for both micellization and adsorption. The nanoparticles (NC10 and NC12) of the prepared surfactants were obtained using the ball mill technique. The particle size and morphology of the nanoparticles were determined using transmission electron microscope measurements. The antibacterial study of the nanoparticle surfactants revealed their strong efficiency against fungi and different pathogenic bacteria compared with the original surfactants.
- El-Shamy, Omnia A. A.,Habib, Amr O.,Mohamed, Dalia E.,Badawi, Abdelfattah M.
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p. 215 - 223
(2019/11/03)
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- Old Concepts, New Application – Additive-Free Hydrogenation of Nitriles Catalyzed by an Air Stable Alkyl Mn(I) Complex
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An efficient additive-free manganese-catalyzed hydrogenation of nitriles to primary amines with molecular hydrogen is described. The pre-catalyst, a well-defined bench-stable alkyl bisphosphine Mn(I) complex fac-[Mn(dpre)(CO)3(CH3)] (dpre=1,2-bis(di-n-propylphosphino)ethane), undergoes CO migratory insertion into the manganese-alkyl bond to form acyl complexes which upon hydrogenolysis yields the active coordinatively unsaturated Mn(I) hydride catalyst [Mn(dpre)(CO)2(H)]. A range of aromatic and aliphatic nitriles were efficiently and selectively converted into primary amines in good to excellent yields. The hydrogenation of nitriles proceeds at 100 °C with a catalyst loading of 2 mol % and a hydrogen pressure of 50 bar. Mechanistic insights are provided by means of DFT calculations. (Figure presented.).
- Weber, Stefan,Veiros, Luis F.,Kirchner, Karl
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supporting information
p. 5412 - 5420
(2019/11/13)
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- Switching the Selectivity of Cobalt-Catalyzed Hydrogenation of Nitriles
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Previous studies of base metals for catalytic hydrogenation of nitriles to primary amines or secondary aldimines focus on designing complexes with elaborate structures. Herein, we report "twin" catalytic systems where the selectivity of nitrile hydrogenation can be tuned by including or omitting the ligand HN(CH2CH2PiPr2)2 (iPrPNHP). Simply treating CoBr2 with NaHBEt3 generates cobalt particles, which can catalyze the hydrogenation of nitriles to primary amines with high selectivity and broad functional group tolerance. Ligating CoBr2 with iPrPNHP followed by the addition of NaHBEt3, however, forms a homogeneous catalyst favoring secondary aldimines for both hydrogenation and hydrogenative coupling of benzonitrile.
- Dai, Huiguang,Guan, Hairong
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p. 9125 - 9130
(2018/09/21)
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- Hydrogenation of Nitriles and Ketones Catalyzed by an Air-Stable Bisphosphine Mn(I) Complex
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Efficient hydrogenations of nitriles and ketones with molecular hydrogen catalyzed by a well-defined bench-stable bisphosphine Mn(I) complex are described. These reactions are environmentally benign and atomically economic, implementing an inexpensive, earth-abundant nonprecious metal catalyst. A range of aromatic and aliphatic nitriles and ketones were efficiently converted into primary amines and alcohols, respectively, in good to excellent yields. The hydrogenation of nitriles proceeds at 100 °C with catalyst loading of 2 mol % and 20 mol % base (t-BuOK), while the hydrogenation of ketones takes place already at 50 °C, with a catalyst loading of 1 mol % and 5 mol % of base. In both cases, a hydrogen pressure of 50 bar was applied.
- Weber, Stefan,St?ger, Berthold,Kirchner, Karl
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supporting information
p. 7212 - 7215
(2018/11/25)
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- Hydrogenation of Aliphatic and Aromatic Nitriles Using a Defined Ruthenium PNP Pincer Catalyst
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Selective catalytic reductions of nitriles are presented using the commercially available Ru-Macho-BH complex. A variety of aliphatic, aromatic and (hetero)cyclic nitriles including industrially important adipodinitrile are hydrogenated to the corresponding primary amines. Modelling suggests the reaction follows an outer sphere hydrogenation mechanism. An efficient and selective catalytic reduction of nitriles is presented using the commercially available Ru-Macho-BH complex. A variety of aliphatic, aromatic and (hetero)cyclic nitriles including the industrially important adipodinitrile are hydrogenated to the corresponding primary amines. The reaction follows an outer-sphere mechanism.
- Neumann, Jacob,Bornschein, Christoph,Jiao, Haijun,Junge, Kathrin,Beller, Matthias
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p. 5944 - 5948
(2015/09/22)
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- Straightforward access to cyclic amines by dinitriles reduction
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1,1,3,3-Tetramethyldisiloxane (TMDS) and polymethylhydrosiloxane (PMHS), when associated with titanium(IV) isopropoxide, provide two convenient systems for the reduction of nitriles into the corresponding primary amines. Kinetics of the two systems have been studied by 1H NMR and demonstrated that reduction with PMHS occurs faster than with TMDS. These two titanium-based systems reduce both aromatic and aliphatic nitriles in the presence of Br, CC, NO2, OH, and cyclopropyl-ring. In the case of cyclopropyl-nitriles, the formation of secondary amines, which come from an intermolecular reductive alkylation reaction was observed. This result was exploited for the reduction of dinitriles, which led, in one-step, to azepane, piperidine, pyrrolidine, and azetidine derivatives through an intramolecular reductive alkylation reaction.
- Laval, Stéphane,Dayoub, Wissam,Pehlivan, Leyla,Métay, Estelle,Favre-Reguillon, Alain,Delbrayelle, Dominique,Mignani, Gérard,Lemaire, Marc
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supporting information
p. 975 - 983
(2014/01/23)
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- A mild and efficient method for the reduction of nitriles
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A simple and useful method for the reduction of nitriles into the corresponding amines using a tetramethyldisiloxane/titanium(IV) isopropoxide reducing system is described. The synthetic approach is straightforward and provides primary amines as hydrochloride salt in almost quantitative yield. Other advantages of this method, such as easy-to-handle hydride source, inert by-products, that is, TiO2 and oligomeric siloxanes, make it very attractive to prepare primary amines.
- Laval, Stéphane,Dayoub, Wissam,Favre-Reguillon, Alain,Berthod, Mika?l,Demonchaux, Patrice,Mignani, Gérard,Lemaire, Marc
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experimental part
p. 7005 - 7007
(2010/02/28)
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- A convenient method for the preparation of primary amines using tritylamine
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A simple method for the preparation of primary amines by treating N-tritylamines with trifluoroacetic acid has been established. The N-tritylamines were prepared by the reaction of alkyl halides or alkyl p-toluenesulfonates with tritylamine, or by the reaction of alkyl bromides with lithium tritylamide.
- Theodorou, Vassiliki,Ragoussis, Valentine,Strongilos, Alexandros,Zelepos, Evangelos,Eleftheriou, Argyro,Dimitriou, Maria
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p. 1357 - 1360
(2007/10/03)
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- Novel methods for the delivery of polynucleotides to cells
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Process are described for the delivery of a polynucleotide to a cell. The process comprises forming a salt stable complex between the polynucleotide and a cationic surfactant. Ternary complexes are also made by associating an amphipathic compound with the binary complex. The resultant complexes are suitable for delivery of the polynucleotide to cells in vitro and in vivo.
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- Pigment compositions containing substituted amido phthalocyanine derivatives
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A pigment composition comprising pigment and an amido phthalocyanine compound having the general formula I:MPc-(CONR1R2)nIwherein which Pc is a phthalocyanine ring which is optionally further substituted by up to an average of one chlorine or bromine atom or of a sulphonic acid; M is hydrogen or a metal such as Mg, Al, Ni, Fe, Zn, Pb, Sn or Cu: n is a number ranging from 0.1 to 4.0; R1 and R2 are independently selected from hydrogen, C1-C20 alkyl, C5-C12 cycloalkyl, C7-C12 aralkyl, C6-C10 aryl, C4-C6 alkyl amino alkyl, C2-C20 aliphatic amine, C2-C20 aliphatic amine acid salt, C2-C20 alcohol, polyoxyalkylene, polyoxyalkylene amine.
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- Process for the preparation of substituted amido phthalocyanine derivatives and novel substituted amido phthalocyanine derivatives
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A process for the preparation of substituted amido phthalocyanines having the general formula I:MPc-(CONR1R2)nIvia the reaction of a phthalocyanine carboxamide having the formula MPc(CONH2)x wherein Pc is a Phthalocyanine ring; M is a hydrogen or a metal capable of forming a metal phthalocyanine such as Mg, Al, Ni, Fe, Zn, Pb, Sn or Cu and x is a number from 0.1 to 4.0, with an amine acid salt denoted by formula II: wherein R1 and R2 are independently selected from the group consisting of hydrogen; an alkyl group having 1-20 carbons; a cyclic alkyl group; an aryl group; an arylalkyl having 1-20 carbons; an alcohol group having 2-20 carbons; an alkyl amino alkyl group; an aliphatic amine having 1-20 carbons; an aliphatic amine acid salt having 1-20 carbons; polyoxyalkylene groups ranging in molecular weight 89-2000; polyoxyalkyleneamines ranging in molecular weight 148-4000; Z is the hydrogen sulphate or the hydrochloride salt of the amine.
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