- Colorimetric and fluorescence sensing of fluoride anions with potential salicylaldimine based schiff base receptors
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Salicylaldimine based schiff base receptors with different substituents showing fluorescent enhancement in the presence of fluoride anion was visualized through naked eye as well as by change in spectral properties (UV-vis and fluorescent techniques). The reason for such fluorescence enhancement may be due to hydrogen bond interaction between receptor recognition site and fluoride anion. Such a hydrogen bond interaction creates a six-membered transition state, which avoids quenching processes. To support this, fluorescence enhancement factor (FEF) was calculated and it was found to be more (FEF = 652) for -NO2 substituted receptor compared to other receptors.
- Sivakumar, Radhakrishnan,Reena, Vijayaragavan,Ananthi, Nallamuthu,Babu, Muthiya,Anandan, Sambandam,Velmathi, Sivan
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- Solvent extraction of copper(II) from sulfate medium with N -(2-hydroxybenzylidene)aniline
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Solvent extraction of copper(II) from sulfate medium with N-(2-hydroxybenzylidene)aniline is studied with the following parameters: pH, concentration of the extractant, nature of diluent, and temperature. The extraction of copper(II) proceeds by a cation
- Aidi,Barkat
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- On the formation of imines in water-a comparison
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The reaction of aniline with aryl aldehydes in water has been investigated in the past, but contradictory results have been published. While only small amounts of imines 3 were detected by NMR analysis, isolation afforded high imine yields. A reinvestigat
- Saggiomo, Vittorio,Lüning, Ulrich
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- Synthesis, spectral studies and DFT calculation of copper(II) complexes with mixed ligands
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The reaction of copper(II) chloride with Schiff bases and alkanolamines in 1:1:1 molar ratio(s) resulted a series of mixed ligand copper(II) complexes of general formula [Cu(sb)(aa)] (1-6), [where sb = Schiff base; salicylidine-1-aminobenzene (sabH) (1,4)
- Kumar, Manoj,Anjum, Afreen,Jaiswal, Nitesh,Dubey, Raj Kumar
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- Redox-active copper triangles as an enzymatic molecular flask for light-driven hydrogen production
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A positively charged redox-active metal-organic triangle containing three redox-active copper centres was developed to encapsulate anionic organic dyes (fluorescein) through a weak host-guest interaction for photocatalytic hydrogen production. The unique
- Zhao, Liang,Wei, Jianwei,Zhang, Feili,He, Cheng,Zheng, Sijia,Duan, Chunying
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- Background defining during the imine formation reaction in FT-IR liquid cell
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Imine formation is a very important chemical reaction because of its relevance to biological process. Therefore, it is crucial to follow whole reaction process in detail. The current work performed to monitor the whole imination reaction in real time in l
- Namli, Hilmi,Turhan, Onur
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- Synergistic extraction of nickel(II) from a sulfate medium by a mixture of N-(2-hydroxybenzylidene)aniline and methyl–isobutyl ketone
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The synergistic solvent extraction of nickel(II) from a sulfate medium with N-(2-hydroxybenzylidene)aniline in the absence and presence of Methyl–Isobutyl Ketone (MIBK) in chloroform at 25°C has been studied. A synergistic effect is observed for the metal
- Almi,Adjel,Barkat
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- Copper complex based on 2-(phenylimino-methyl)-phenol as a high selective fluoresencent probe for hydrogen sulfide
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A Copper(II) complex of condensation production was synthesized and its crystal was also obtained by the reaction of 2-(phenylimino-methyl)-phenol with Cu(CH3COO)2·H2O. The crystal and molecular structure of the complex wa
- Ren, Kui,Shang, Xuefang,Fu, Jiajia,Zhao, Peipei,Zhang, Jinlian
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- In-Situ Photochromism Switching with Crystal Jumping through the Deammoniation of N-Salicylideneaniline Ammonium Salt
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N-Salicylideneaniline (SA) derivatives are traditional organic photochromic compounds whose properties are closely related to their molecular conformations and crystal structures. We herein present the photochromic property switching phenomenon of SA ammonium salt crystals using a deammoniation reaction. The N-salicylidene-4-carboxyaniline ammonium salt crystal (1-Sα) was found to exhibit photochromism upon irradiation with UV light. Upon heating, 1-Sα desorbed ammonia gas and transformed into a nonionic SA crystal (1-N) with non-photochromic properties. Surprisingly, this phase transition induced the "jumping crystal" phenomenon. Thus, the crystal structures both before and after the phase transition were determined, and it was revealed that the switching phenomenon of photochromism (photochromism switching) was caused by the crystal structural and molecular conformational changes that took place upon deammoniation. In addition, 1-N reverted to 1-Sα by exposure to aqua-ammonia vapor for a few minutes. These results suggested that such SA crystals could be applicable as switching materials or chemical sensors.
- Sugiyama, Haruki,Johmoto, Kohei,Sekine, Akiko,Uekusa, Hidehiro
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- A novel water-soluble multicolor halo- And photochromic switching system based on a nitrile-rich acceptor
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A directed synthesis of the first nitrile-rich dye showing visible-light-induced negative photochromism in aqueous medium was implemented. The possibility to change the color of an aqueous solution from yellow to magenta by varying the pH from 5 to 8 was
- Belikov, Mikhail Yu.,Ievlev, Mikhail Yu.,Bardasov, Ivan N.
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supporting information
p. 10287 - 10295
(2021/06/18)
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- A novel water-dispersible and magnetically recyclable nickel nanoparticles for the one-pot reduction-Schiff base condensation of nitroarenes in pure water
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In this work, a heterogeneous nanocatalyst called Ni-Fe3O4@Pectin~PPA ~ Piconal was first synthesized, which was investigated as a bifunctional catalyst containing nickel functional groups. On the other hand, this Ni-Fe3O4@Pectin~PPA ~ Piconal catalyst in aqueous solvents shows a very effective performance at ambient temperature for the nitroarene reduction reaction with sodium borohydride, for which NaBH4 is considered as a reducing agent. This is a novelty magnetic catalyst that was approved by various methods, including Fourier-transform infrared spectroscopy (FT-IR), X-ray powder diffraction (XRD), Dynamic light scattering (DLS), Transmission electron microscopy (TEM), vibrating sample magnetometer (VSM), Inductively coupled plasma (ICP), Energy-dispersive X-ray spectroscopy (EDX), and Field emission scanning electron microscopy (FESEM) analyses. From the satisfactory results obtained from the reduction of nitrogen, this catalytic system is used for a one-pot protocol containing a reduction-Schiff base concentration of diverse nitroarenes. It was corroborated with the heterogeneous catalytic experiments on the one-pot tandem synthesis of imines from nitroarenes and aldehydes. Finally, the novel Ni-Fe3O4@Pectin~PPA ~ Piconal catalyst could function as a more economically desirable and environmentally amicable in the catalysis field. The favorable products are acquired in good to high performance in the attendance of Ni-Fe3O4@Pectin~PPA ~ Piconal as a bifunctional catalyst. This catalyst can be recycled up to six steps without losing a sharp drop.
- Ghamari Kargar, Pouya,Ravanjamjah, Asiye,Bagherzade, Ghodsieh
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p. 1916 - 1933
(2021/07/10)
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- Structural studies and applications of water soluble (phenoxy)imine palladium(II) complexes as catalysts in biphasic methoxycarbonylation of 1-hexene
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Reactions of the ligands; sodium 4?hydroxy-3-((phenylimino)methyl)benzenesulfonate (L1), sodium 3-(((2,6-dimethylphenyl)imino)methyl)-4-hydroxybenzenesulfonate (L2) and sodium 3-(2,6-diisopropylphenyl)imino)methyl)-4-hydroxybenzenesulfonate (L3) with Pd(OAc)2 afforded the respective palladium(II) complexes [Pd(L1)2] (PdL1), [Pd(L2)2] (PdL2) and [Pd(L3)2] (PdL3). In addition, treatment of the non-water soluble ligands 2-((phenylimino)methyl)phenol (L4), 2-(((2,6-dimethylphenyl)imino)methyl)phenol (L5) and 2-((2,6-diisopropylphenyl)imino)methyl)phenol (L6) with Pd(OAc)2 gave the corresponding complexes [Pd(L4)2] (PdL4), [Pd(L5)2] (PdL5) and [Pd(L6)2] (PdL6) in good yields. Solid state structures of complexes PdL1 and PdL4 established the formation of bis(chelated) square planar neutral compounds. All the complexes formed active catalysts in the methoxycarbonylation of 1-hexene, affording yields of up to 92% within 20 h and regioselectivity of 73% in favour of linear esters. The catalytic activity and selectivity of the complexes depended on the steric encumbrance around the coordination centre. The water soluble complexes displayed comparable catalytic behaviour to the non-water soluble systems. The complexes could be recycled five times with minimal changes in both the catalytic activities and regio-selectivity.
- Akiri, Saphan O.,Ojwach, Stephen O.
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supporting information
(2021/04/27)
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- Spectroscopic identification of hydrogen bond vibrations and quasi-isostructural polymorphism in n-salicylideneaniline
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The ortho-hydroxy aryl Schiff base 2-[(E)-(phenylimino)methyl]phenol and its deutero-derivative have been studied by the inelastic incoherent neutron scattering (IINS), infrared (IR) and Raman experimental methods, as well as by Density Functional Theory
- Hetmańczyk, ?ukasz,Goremychkin, Eugene A.,Waliszewski, Janusz,Vener, Mikhail V.,Lipkowski, Pawe?,Tolstoy, Peter M.,Filarowski, Aleksander
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- Schiff-base molecules and COFs as metal-free catalysts or silver supports for carboxylation of alkynes with CO2
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Carboxylation of terminal alkynes with CO2 to produce propiolic acids is an atom economical and high-value route for CO2 fixation and utilization, but the conversion under mild conditions needs transition metal catalysts. In this article, we demonstrated for the first time the transition-metal-free organocatalysts for the reaction. The efficient catalysts are Schiff bases derived from 1,3,5-triformylphloroglucinol (Tp), either homogeneous (discrete molecules) or heterogeneous (covalent organic frameworks, COFs). The key catalytic sites are phenoxo and imine groups, which activate CO2 through phenoxo-CO2 complexation and also activate the C(sp)-H bond through bifurcate C-H?Nimine and C-H?Ophenoxo hydrogen bonds. The 2,2′-bipyridyl sites in the COF also contribute to the catalytic performance. The COF catalyst is less active than the molecular one but has the advantages of heterogeneous catalysis. Higher performance was also demonstrated by combining silver nanoparticles (AgNPs) with the intrinsically catalytic COF. This work opens up the potential of developing transition-metal-free catalysts for the CO2 conversion reaction and demonstrates the new prospects of COFs as tailorable platforms for heterogeneous catalysis.
- Bu, Ran,Gao, En-Qing,Liu, Xiao-Yan,Mu, Peng-Fei,Zhang, Lin
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supporting information
p. 7620 - 7629
(2021/10/12)
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- Facile synthesis, solublization studies and anti-inflammatory activity of amorphous zinc(Ii) centered aldimine complexes
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In this study, Zn(II) centered complexes with aldimine derivatives were synthesized using green solvent, polyethylene glycol (PEG-400) and amorphous complexes were characterized by FT-IR, multinuclear (1H and13C NMR), elemental and thermal analysis. Thermogravimetric analysis indicated the extended thermal stability of the synthesized complexes. All the Zn(II) complexes show very significant photoexcitation in the range of 318 – 384 nm and photoemission in the range of 502 – 562 nm. Among all the complexes, Zn(II) complex (3Zn) showed minimum band gap value, 2.35 eV. These amorphous complexes have been reported for their wide applications in biomedical sciences. The synthesized aldimine ligands and Zn(II) complexes were investigated for anti-inflammatory activity and these complexes showed more anti-inflammatory potential than the corresponding aldimine ligands. The solubilization of zinc complexes in sodium dodecyl sulphate was also investigated to reveal the interaction of metal complexes by using UV-Visible spectroscopy and electrical conductivity measurements.
- Ali, Uzma,Alshater, Heba,Imran, Muhammad,Maalik, Aneela,Noor, Sadia,Qureshi, Ahmad Kaleem,Raheel, Ahmad,Sharif, Muhammad,Taj, Muhammad Babar,Tirmizi, Syed Ahmad
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p. 929 - 941
(2021/06/26)
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- In silico, in vitro and in vivo studies indicate resveratrol analogue as a potential alternative for neuroinflammatory disorders
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Inflammaging is known as an imbalance between pro-inflammatory and anti-inflammatory immune mechanisms, being related to the onset of neurological disorders, such as major depression and Alzheimer's disease. Considering the known disadvantages regarding the FDA approved drug to manage such illnesses, resveratrol emerges as a natural drug candidate, despite its low bioavailability. In this study, resveratrol analogues were evaluated for their capacity of inhibiting acetylcholinesterase in silico, in vitro, and in vivo. Molecular docking simulations pointed out RSVA1 and RSVA6 as potent inhibitors, even more than resveratrol. Ellman's assay demonstrated RSVA6 as capable of inhibiting 92.4% of the enzyme activity. Further, male Swiss mice were pretreated with RSVA6 (100 mg kg?1) 60 min before receiving scopolamine (1 mg kg?1). The Novel Recognition Object (NOR), Object Location (OLT), and Buried Pellet tests (BPL) demonstrated an RSVA6 neuroprotective effect. In the second round of tests, mice received a single intraperitoneal injection of lipopolysaccharide (0.5 mg kg?1) 24 h before treatment with RSVA6 (1, 10, and 100 mg kg?1). The Open Field (OFT), Tail Suspension (TST), and Splash tests (ST) were evaluated. LPS had no significant effect on the crossing and rearing number, indicating an association between the immobility time and anhedonia observed in the TST and ST, respectively, with depressive-like behavior. RSVA6 significantly reduced the depressive-like behavior triggered by LPS in the TST and ST. Altogether, our data suggest RSVA6 as a potential drug candidate for the treatment of neuroinflammatory conditions.
- Dutra, Rafael Cypriano,Goliatt, Priscila Vanessa Zabala Capriles,Marion, Gabriel Macedo,Meinel, Raissa Soares,Nunes, Vinicius Schmitz Pereira,da Silva, Adilson David,Fávero, Amanda,Menegasso, Jaíne Ferrareis,Raposo, Nádia Rezende Barbosa,de Assis, Pollyana Mendon?a
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- Blue Highly Fluorescent Boranil Derived From Anil Ligand: Synthesis, Characterization, Experimental and Theoretical Evaluation of Solvent Effect on Structures and Photophysical Properties
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In this study, we report the design and the synthesis of a Schiff base; Anil and its corresponding Boron Difluoride complexe; Boranil. The synthesis procedure was carried out adopting new, optimized reaction conditions. The Boranil dye presents the advantage to be emissive in solution. 1H and 19F NMR along with FTIR confirmed both compound's structure. To gain a better understanding of the solvatochromic behavior of Anil and Boranil, the dependence of the absorption spectra on the solvent's polarity was studied in depth. Thus, UV–Vis spectroscopy was performed in five selected solvents. In addition to the solvent's polarity effect, the influence of BF2 moiety introduction on the molecule's photophysical properties was also evaluated. When examining different absorption spectra, we found that the title fluorescent dye exhibited weak solvatochromic (11 nm in THF) as well as a slight redshift broader and relatively more structured absorption spectra after complexation. Besides, we investigate the obtained key structure–property relationships through DFT and TD-DFT calculations using a 6–311++ G (d, p) basis set. Quantum chemical calculations allowed confirming proposed structures and understanding their electronic structure in larger details. Theoretical results also showed good agreement with the experimental findings. Finally, the frontier molecular orbitals were investigated to illustrate the pi-conjugation and charge transfer effect.
- Agren, Soumaya,Chaabene, Marwa,Allouche, Abdul-Rahman,Ben Chaabane, Rafik,Lahcinie, Mohamed,Baouab, Mohamed Hassen V
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- Ruthenium N-Heterocyclic Carbene Complexes for Chemoselective Reduction of Imines and Reductive Amination of Aldehydes and Ketones
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Chemoselective reduction of imines to secondary amines is catalyzed efficiently by tethered and untethered, half-sandwich ruthenium N-heterocyclic carbene (NHC) complexes at room temperature. The untethered Ru-NHC complexes are more efficient as catalysts for the reduction of aldimines and ketimines than the tethered complexes. Using the best untethered complex as a catalyst, electronic and steric demands on the reaction was probed using a series of imines. Chemoselectivity of the catalyst towards imine reduction was tested by performing inter and intramolecular competitive reactions in a variety of ways. The catalyst exhibits a very high TON and TOF under anaerobic conditions.
- Kathuria, Lakshay,Samuelson, Ashoka G.
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supporting information
(2020/06/17)
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- Simple synthesis of the novel Cu-MOF catalysts for the selective alcohol oxidation and the oxidative cross-coupling of amines and alcohols
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A novel porous metal–organic framework {Cu2(bbda)0.5(Hbbda)1.5(OAc)1.5.8H2O} (UoB-5) was synthesized under ultrasound irradiation by employing a new Schiff base ligand H2bbda (4,4'(1,4-phenylene bis (azanylylidene)) bis (methanylylidene))dibenzoic acid) and was fully characterized. The microporous nature of UoB-5 was confirmed by gas-sorption measurements. This framework acted as a highly effective heterogeneous catalyst for the alcohol oxidation reaction with tert-butyl hydroperoxide (t-BuOOH) as an oxidant. The presence of coordinatively unsaturated metal sites in UoB-5 could be the reason for high performance in this reaction. Furthermore, using the long linker with the free -NC group and uncoordinated -N atom on the wall of the pores created UoB-5 an excellent candidate for the catalytic activities without activation of the framework. It was confirmed with the heterogeneous catalytic experiments on the one-pot tandem synthesis of imines from benzyl alcohols and anilines. Eventually, the new Cu-MOF (UoB-5) could be an alternative catalyst as a more economically favorable and environmentally friendly in the catalysis field.
- Ghamari Kargar, Pouya,Aryanejad, Sima,Bagherzade, Ghodsieh
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- AIPE-active platinum(ii) complexes with tunable photophysical properties and their application in constructing thermosensitive probes used for intracellular temperature imaging
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Aggregation-induced phosphorescent emission (AIPE) luminogens based on phosphorescent transition metal complexes have many application advantages in bioimaging compared with fluorescent organic dyes because of their long excitation lifetime and reduced ph
- Lin, Shengheng,Pan, Honghao,Li, Lin,Liao, Rui,Yu, Shengzhen,Zhao, Qiang,Sun, Huibin,Huang, Wei
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supporting information
p. 7893 - 7899
(2019/07/10)
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- Switching the N-Alkylation of Arylamines with Benzyl Alcohols to Imine Formation Enables the One-Pot Synthesis of Enantioenriched α-N-Alkylaminophosphonates
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The selective N-alkylation of anilines with benzylic alcohols can be switched in favor of the dehydrogenative condensation process using the nitrile-ligated Kn?lker's complex by conducting the reaction either in a closed system under inert conditions, or in an open system in air. The selective formation of imines, containing reactive C=N bonds, provides an opportunity towards further functionalization. Indeed, a one-pot three-component condensation of alcohols, amines and phosphites, promoted by an iron-based Kn?lker-type complex in combination with a chiral BINOL-based phosphoric acid, provides access to enantioenriched α-N-alkylaminophosphonates.
- Hofmann, Natalie,Hultzsch, Kai C.
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supporting information
p. 3105 - 3111
(2019/06/08)
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- Single-Pot Synthesis Method of 2-Hydroxybenzylidene-4-[(aza, thio)xanthenyl]anilines and Their Plant Growth Regulator Activity
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The synthesis of 2-hydroxybenzylidene-4-[(aza, thio)xantenyl]anilines has been carried out via the reaction of 2-hydroxybenzaldehyde, aniline, and (aza, thio)xanthydrol in acetic acid or ethanol medium. Two competing pathways leading the formation of 2-hy
- Gorokhov, V. Yu.,Bykov, Ya. V.,Batuev,Lystsova,Gorokhova,Yaganova
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p. 663 - 667
(2019/06/05)
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- A new bifunctional heterogeneous nanocatalyst for one-pot reduction-Schiff base condensation and reduction-carbonylation of nitroarenes
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In this work, synthesis of Pd-NHC-γ-Fe2O3-n-butyl-SO3H and its activity as a bifunctional heterogeneous nanocatalyst containing Pd-NHC and acidic functional groups, are described. This newly synthesized nanomagnetic catalyst is fully characterized by different methods such as FT-IR, XPS, TEM, VSM, ICP and TG analysis. At first, the catalytic activity of Pd-NHC-γ-Fe2O3-n-butyl-SO3H is evaluated for the reduction of nitroarenes in aqueous media using NaBH4 as a clean source of hydrogen generation at ambient temperature. Using the promising results obtained from the nitroarene reduction, this catalytic system is used for two one-pot protocols including reduction-Schiff base condensation and reduction-carbonylation of various nitroarenes. In these reactions the in situ formed amines are further reacted with aldehydes to yield imines or carbonylated to amides. The desired products are obtained in good to high yields in the presence of Pd-NHC-γ-Fe2O3-n-butyl-SO3H as a bifunctional catalyst. The catalyst is reused with the aid of a magnetic bar for up to six consecutive cycles without any drastic loss of its catalytic activity.
- Sobhani, Sara,Chahkamali, Farhad Omarzehi,Sansano, José Miguel
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p. 1362 - 1372
(2019/01/24)
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- Conversion of aldimines to secondary amines using iron-catalysed hydrosilylation
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Iron-catalyzed hydrosilylation of imines to amines using a well-defined iron complex is reported. This method employs relatively mild conditions, by reaction of imine, (EtO)3SiH in a 1 : 2 ratio in the presence of 1 mol% precatalyst ([BIAN]Fe(η6-toluene), 3, BIAN = bis(2,6-diisopropylaniline)acenaphthene) at 70 °C. A broad scope of imines was readily converted into the corresponding secondary amines without the need for precatalyst activators.
- Saini, Anu,Smith, Cecilia R.,Wekesa, Francis S.,Helms, Amanda K.,Findlater, Michael
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supporting information
p. 9368 - 9372
(2019/01/03)
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- Method of synthesizing imine and amine compounds by means of borrowing-hydrogen reduction coupling
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The invention belongs to energy and chemical industry and particularly relates to a method of synthesizing imine and amine compounds by means of borrowing-hydrogen reduction coupling by using a nitrogen-doped hierarchical-porous biomass-based carbon material supported catalyst. The method includes the steps of: under a seal reaction condition, adding a nitro-aromatic hydrocarbon compound, benzyl alcohol compounds with different substituent groups, the supported catalyst, methylbenzene and potassium tert-butoxide; performing a reaction at 50-150 DEG C for 4-24 h, cooling the product to room temperature and filtering a reaction liquid to obtain the imine compound represented in the formula (1) or the amine compound represented in the formula (2). The raw materials of the catalyst are regenerable resources, are widely distributed, are green and environment-friendly, are easy to prepare and abundant in sources, and are low in cost; the catalyst can be recycled without deactivation and is stable to air, water and heat. By means of the supported metal catalyst, the conversion rate of the borrowing-hydrogen reduction coupling reaction on the nitro-compound and alcohol to prepare the iminecompounds is higher than 99%, and yield can reach 90-60%; the conversion rate of same to prepare the amine compounds is higher than 99%, and yield can reach 90-60%.
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Paragraph 0043; 0044; 0045; 0046; 0049
(2018/11/04)
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- PdCl2(Ph3P)2/Salicylaldimine Catalyzed Diarylation of Anilines with Unactivated Aryl Chlorides
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Triphenylphosphine and salicylaldimine could be used as a mixed ligand system to obtain a high catalytic activity for palladium catalyzed diarylation of primary anilines with unactivated aryl chlorides by the synergistic effect of ligands. The activity and selectivity of the catalytic system could be improved by modifying the structure of salicylaldimine. In refluxing o-xylene, PdCl2(Ph3P)2 with 2,5-ditrifluoromethyl N-phenylsalicylaldimine as a coligand shows high efficiency for the diarylation of various anilines. The catalytic system shows good toleration for the steric hindrance of the substrates. The facile catalytic system works as well on the multiple arylation of 1,1′-biphenyl- 4,4′-diamine with aryl chlorides to afford N,N,N′,N′-tetraaryl-1,1′-biphenyl-4,4′-diamines which are important intermediates of organic light emitting diode (OLED) hole transport materials.
- Tao, Xiaochun,Li, Lei,Zhou, Yu,Qian, Xuanying,Zhao, Min,Cai, Liangzhen,Xie, Xiaomin
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p. 1749 - 1754
(2017/10/06)
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- An erasable photo-patterning material based on a specially designed 4-(1,2,2-triphenylvinyl)aniline salicylaldehyde hydrazone aggregation-induced emission (AIE) molecule
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Luminescent molecules with photochromic properties show strong potential in molecular switches, molecular logic gates, photo-controllable materials, bio-imaging, anti-counterfeiting, photo-patterning, etc. However, research is still scarce in such molecul
- Wang, Lili,Li, Yuanyuan,You, Xuejiao,Xu, Kui,Feng, Qi,Wang, Jinmin,Liu, Yuanyuan,Li, Kai,Hou, Hongwei
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- Rhodium-catalysed hydroformylation of 1-octene using aryl and ferrocenyl Schiff base-derived ligands
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Monometallic and heterobimetallic complexes of Rh(I) bearing chelating N,O-bidentate aryl- and ferrocenyl-derived ligands have been synthesised via Schiff base condensation reactions, and characterised fully using 1H NMR, 13C{1H} NMR and Fourier transform infrared spectroscopies, elemental analysis and mass spectrometry. The new monometallic and heterobimetallic complexes were evaluated as potential catalyst precursors in the hydroformylation of 1-octene at 95°C and 40?bar. The ferrocenylimine mononuclear compounds were inactive in the hydroformylation experiments. The Rh(I) monometallic and the ferrocene–Rh(I) heterobimetallic pre-catalysts displayed good activity and conversion of 1-octene as well as outstanding chemoselectivity towards aldehydes in the hydroformylation reaction.
- Siangwata, Shepherd,Chulu, Sisasenkosi,Oliver, Clive L.,Smith, Gregory S.
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- Carbocation Organocatalysis in Interrupted Povarov Reactions to cis-Fused Pyrano- and Furanobenzodihydropyrans
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Tritylium cation-catalyzed interrupted Povarov reactions afforded cis-4-aminobenzodihydropyrans in excellent yields (90 %) within 10 min by low catalyst loadings (1 mol-%). A mechanism involving Lewis acidic catalysis by a carbocation was proposed and val
- Liu, Jingjing,Xu, Jiaxi,Li, Zhenjiang,Huang, Yu,Wang, Haixin,Gao, Yu,Guo, Tianfo,Ouyang, Pingkai,Guo, Kai
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p. 3996 - 4003
(2017/07/28)
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- Nanosilica-anchored Pd(II)-Schiff base complex as efficient heterogeneous catalyst for activation of aryl halides in Suzuki–Miyaura cross-coupling reaction in water
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A nanosilica (derived from rice husk)-anchored Pd(II)–Schiff base complex has been synthesized and characterized. This immobilized complex has been found to be a very effective and recyclable heterogeneous catalyst for the Suzuki–Miyaura cross-coupling reaction of various aryl halides with arylboronic acid in aqueous medium under mild conditions. The products were identified using 1H NMR and mass spectral studies. This complex can be easily filtered out from the reaction medium and reused up to six times without significant loss of catalytic activity. Since the reaction proceeds under mild conditions in aqueous medium as well as the catalyst being recyclable, it provides an environmentally benign alternative route to the existing protocols for the Suzuki–Miyaura reaction.
- Gogoi, Nibedita,Bora, Utpal,Borah, Geetika,Gogoi, Pradip K.
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- Catalyst-free allylation of 2-aminophenol–derived aldimines with allyltrichlorosilane under thermal conditions
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Allylation of 2-aminophenol-derived aldimines using allyltrichlorosilane under catalyst free conditions has been developed. This reaction afforded the corresponding homoallylic amines in good to excellent yields (68–94%). The salicylaldehyde-derived aldimines as well as benzoylhydrazone also found to react with allyltrichlorosilane smoothly under the same conditions, to furnish the corresponding homoallylic amine derivatives. This study suggests that the phenolic –OH group acts as an anchoring group for the transfer of allyl group from allyl silane reagent.
- Venkatanna, Kesa,Ramanathan, Chinnasamy Ramaraj
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supporting information
p. 3650 - 3653
(2017/08/22)
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- Oxazine Ring-Related Vibrational Modes of Benzoxazine Monomers Using Fully Aromatically Substituted, Deuterated, 15N Isotope Exchanged, and Oxazine-Ring-Substituted Compounds and Theoretical Calculations
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Polymerization of benzoxazine resins is indicated by the disappearance of a 960-900 cm-1 band in infrared spectroscopy (IR). Historically, this band was assigned to the C-H out-of-plane bending of the benzene to which the oxazine ring is attach
- Han, Lu,Iguchi, Daniela,Gil, Phwey,Heyl, Tyler R.,Sedwick, Victoria M.,Arza, Carlos R.,Ohashi, Seishi,Lacks, Daniel J.,Ishida, Hatsuo
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p. 6269 - 6282
(2017/09/01)
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- Abnormal effect of hydroxyl on the longest wavelength maximum in ultraviolet absorption spectra for bis-aryl Schiff bases
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Two sets of bis-aryl Schiff bases that contain 4(or 4′)-OH and 2(or 2′)-OH were synthesized. The first set consists of 4-HOArCH=NArY and XArCH=NArOH-4′, and the second set consists of 2-HOArCH=NArY and XArCH=NArOH-2′. Their ultraviolet absorption spectra were measured and investigated. A very interesting phenomenon was observed by analyzing their wave number νmax (cm?1) of longest wavelength maximum λmax (nm) of ultraviolet. Compared with the change regularity of the νmax of XArCH=NArY (where the X and Y excluded OH), the 4′-position hydroxyl (4′-OH) and 2′-position hydroxyl (2′-OH) have abnormal performance. The details are the following: the 4′-OH contributes an additional red shift to the νmax of XArCH=NArOH-4′ (λmax increase), whereas the 2′-OH contributes an additional blue shift to the νmax of XArCH=NArOH-2′ (λmax decrease). In addition, there are ortho steric effects of all 2-OH and 2′-OH on the νmax for 2-HOArCH=NArY and XArCH=NArOH-2′, and the ortho steric effect contributes a red shift to their νmax. These experimental facts can provide an important theoretical reference for us using aryl Schiff base compounds as optical materials and performing the molecular design.
- Cao, Chao-Tun,Zhou, Wei,Cao, Chenzhong
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- Remarkable difference between five- and six- number-membered ring transition states for intramolecular proton transfer in excited state
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In this study, a range of organic dyes were prepared to investigate difference between five- and six- number-membered ring transition states for internal proton transfer in excited state. Different strength intramolecular hydrogen bond in the target dyes
- Qin, Xiaozhuan,Ding, Ge,Wang, Zhenqiang,Zhang, Shengtao,Li, Hongru,Luo, Ziping,Gao, Fang
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- Schiff base type compound, and preparation method and pharmaceutical purpose thereof
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The invention discloses a Schiff base type compound with a structural formula shown as a formula I, a preparation method and application to medicine preparation by using the compound shown as the formula I or biological acceptable salt as active ingredients. The Schiff base type compound achieves a good effect for inhibiting the tumor cell growth when being applied to medicine for treating tumor diseases. The formula I is shown in the description.
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Paragraph 0056-0060; 0062
(2017/08/31)
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- Preparation method for imine compounds
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The invention relates to a preparation method for imine compounds. The preparation method comprises the following concrete steps: with toluene or derivatives thereof and aminated compounds as reaction substrates, adding an oxygen source under the action of a catalyst; putting the above-mentioned substances into a pressure container, enclosing the pressure container and carrying out a stirring reaction at 50 to 150 DEG C for 6 to 24 h; and carrying out oxidative condensation so as to prepare the imine compounds. The method is characterized in that a metal oxide is used as the catalyst. According to the method, raw materials are cheap and easily available; the prepared imine compounds are easily separable from the catalyst; the catalyst can be cyclically used; reaction process is simple, controllable and easy to operate; and the yield of the imine compounds is as high as 90%.
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Paragraph 0124; 0125
(2017/10/25)
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- Synthetic method of imine
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The invention relates to a method for preparing imine from an azo compound and an alcohol compound through hydrogen transition coupling. The method specifically comprises: dispersing and dissolving an azo compound and an alcohol compound which are taken as substrates in an organic solvent, adding a nickel-based catalyst, putting the obtained mixture in a synthesis kettle, leading inert gas in to replace internal air, performing sealing and stirring, carrying out a heating reaction, performing centrifugation to remove the catalyst after the reaction is over, performing rotary evaporation to remove the solvent, and performing purification through recrystallization to obtain the sample. In the catalytic action of different multi-phase nickel-based catalysts, the reaction is high in conversion rate and imine selectivity. The method is an atom economic reaction.
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Paragraph 0073; 0074
(2017/06/02)
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- Synthesis of (NHC)Pd(salicylaldimine)Cl complexes through template-directed ortho-aromatic metaloxylation of NHC-palladacycles derived from arylimines
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Reactions of imidazoliums with palladacycles afforded NHC-palladacycle complexes. The reactivity of the NHC-palladacycles was explored and the results demonstrated that they could be template-directed ortho-aromatic metaloxylated in the presence of tert-b
- Yang, Jin
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p. 5003 - 5007
(2017/04/17)
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- Synthesis, structure and catalytic activity of bis(phenoxyiminato)iron(III) complexes in coupling reaction of CO2 and epoxides
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Here we described the synthesis and characterization of a series of new bis(phenoxyiminato)Fe(III)-chloro complexes using a variety of techniques, including: elemental analysis, IR-, MS(EI), UV-Vis-spectroscopy, and X-ray diffraction. A solid-state structure of bis(N-salicylidene-3-phenylpropylamine)iron(III)chloride reveals a distorted square-pyramid coordination with crystallographic C2-symmetry wherein chloride occupies the axial position. Isolated complexes were also evaluated as catalysts for a coupling reaction of CO2 and various epoxides, including propylene, 1-hexene, cyclohexene and styrene oxides to form corresponding cyclic carbonates. Accordingly, the ligand structure and the solvent used influenced the catalytic activity and marked enhancement in the activity was observed using DMF as a solvent. Under optimized reaction conditions (145 °C and 10 bar of CO2) bis(N-salicylidene-2-phenylethylamine)iron(III)chloride gave cyclopropylene carbonate with considerable high TON value (1029) within 3 h.
- Al-Qaisi, Feda'a,Genjang, Nevil,Nieger, Martin,Repo, Timo
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- Altering the Photochromic Properties of N-Salicylideneanilines Using a Co-Crystal Engineering Approach
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In this work photochromic properties of N-salicylideneanilines were modified using a crystal engineering approach. Co-crystallization allowed modification of the structural arrangement and electronic properties of the target compounds altering its photoch
- Mercier, Gabriel M.,Robeyns, Koen,Leyssens, Tom
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p. 3198 - 3205
(2016/06/14)
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- Influence of ferrocene and transition metals on the biological activities of Schiff bases
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A series of organic and organometallic Schiff bases bearing phenylferrocene and their six transition metal complexes have been prepared and tested for their potential biological applications by using antifungal, antibacterial, antitumor activities, toxici
- Shah, Faiz Ullah,Jamil, Maryam,Aslam, Javaria,Gul, Asghari,Akhter, Zareen,Mirza, Bushra
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p. 1112 - 1120
(2017/01/25)
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- Extraction behavior of copper(II) with salicylidene aniline and salicylidene toluidine isomers in chloroform from sulfate medium
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The solvent extraction of copper(II) from aqueous sulfate solutions was studied using salicylideneaniline and the three isomeric salicylidenetoluidine diluted with chloroform at 25°C. The molecules of these extractants are studied theoretically using ab i
- Almi, Sana,Benakcha, Rachid,Barkat, Djamel
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p. 274 - 279
(2015/10/12)
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- Activation of aryl chlorides in water for Suzuki coupling with a hydrophilic salen-Pd(II) catalyst
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For exploiting aqueous condition, we have designed a simple water-soluble palladium Schiff-base catalyst for Suzuki-Miyaura reactions of aryl halides with arylboronic acids. The reactions could be performed in neat water with aryl bromides and iodides at room temperature and with aryl chlorides at 100 °C. Good-to-excellent yields of cross-coupling products were obtained with a diverse range of aryl halides including heteroaryl halides. Interestingly, the homogeneous catalyst could be conveniently recycled with aryl bromides or chlorides for at least four times, although a progressive decrease in the product yields were noticed.
- Shahnaz, Nasifa,Puzari, Amlan,Paul, Bidisha,Das, Pankaj
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- ELECTROLUMINESCENT DEVICE USING AZOMETHINE-LITHIUM-COMPLEX AS ELECTRON INJECTION LAYER
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In OLEDs, improved efficiency is obtained by compounds which can form inter alia electron injection layers of the formula (I) wherein R1 is a 1-5 ring aryl (including polycyclic), aralkyl or heteroaryl group which is optionally substituted with one or mor
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Paragraph 0162 - 0164
(2016/10/07)
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- Schiff base metal manganese complex and preparation method and application thereof
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The invention discloses a Schiff base metal manganese complex and a preparation method and application thereof.The method includes the steps of making salicylaldehyde and aniline react to obtain N-phenyl salicylaldehyde imine, making N-phenyl salicylaldehyde imine react with sulfamic acid and sodium carbonate with urea as the catalyst to obtain sulfo salicylic aldehyde, making sulfo salicylic aldehyde react with cyanide urea to obtain sulfo salicylic aldehyde condensation cyanide urea ligand, and coordinating ligand with metal manganese salt to obtain the Schiff base metal manganese complex.Sulfo salicylic aldehyde condensation cyanide urea ligand obtained through the technical scheme has excellent water solubility; the metal manganese complex obtained by coordinating ligand with metal manganese salt has high capacity for catalyzing peroxide hydrogen decomposition and producing many bleaching activity components; the complex further contains amido bonds or like amido bonds and cyano groups, so hydrogen peroxide decomposition can be accelerated to produce bleaching activity substances; due to cyano groups of short carbon chains, peroxide hydrogen decomposition can be easily catalyzed by the Schiff base metal manganese complex, the complex can be applied for bleaching peroxide hydrogen of fabric at low temperature, and the processed fabric has the advantages of being high in whiteness and excellent in capillary effect.
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Paragraph 0011; 0017
(2016/10/09)
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- The effect of solvent on electronic absorption bands of some Benzylideneanilines
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In the present investigation the effects of solvents of varied polarities on the UV–visible spectral bands of some substituted benzylideneanilines and their o/p-hydroxy derivatives were explored. The analyses of the electronic absorption bands indicated t
- Panigrahi, Sagarika,Misra, Pramila K.
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- Palladium-Catalyzed Regioselective C-Benzylation via a Rearrangement Reaction: Access to Benzyl-Substituted Anilines
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An unprecedented C-benzylation rearrangement reaction, catalyzed by palladium, is reported. The reaction proceeds by rearrangement leading to the direct synthesis of para or ortho benzyl-substituted N-methylanilines. The product is obtained in high regioselectivity, without the need to use a ligand for the catalytic process.
- Amézquita-Valencia, Manuel,Alper, Howard
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supporting information
p. 16774 - 16778
(2016/11/17)
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- The evaluation of the role of C-H?F hydrogen bonds in crystal altering the packing modes in the presence of strong hydrogen bond
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Interactions involving fluorine is an area of contemporary research. To unravel the importance of weak C-H?F hydrogen bonds and C-H?π interactions in organic compounds in the presence of strong hydrogen bond, a series of N-benzylideneanilines with simultaneously hydroxyl (-OH) and fluorine substitutions were synthesized for structural analysis. These compounds have been studied through experimental single crystal X-ray diffraction analysis and computational methods (Gaussian09 and AIM2000). The hydroxyl group present in all the molecules were found to form strong O-H?N hydrogen bond, but the spatial arrangement of the molecules connected by this hydrogen bond have been found to be controlled by the weak C-H?F and C-H?O hydrogen bonds, weak C-H?π and π?π interactions. This manuscript illustrates the importance of several weaker interactions in altering the packing modes in the presence of strong hydrogen bonds.
- Kaur, Gurpreet,Singh, Sandhya,Sreekumar, Amritha,Choudhury, Angshuman Roy
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p. 154 - 169
(2015/11/18)
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- Triggering effect caused by elemental sulfur as a mean to reduce the polymerization temperature of benzoxazine monomers
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Mixtures of different benzoxazine resins and elemental sulfur (S8) are prepared and then reacted at 120 °C, below the temperature for radical formation of sulfur. The progress of the reaction and the chemical structures of the main products are monitored and characterized by proton nuclear magnetic resonance spectroscopy (1H NMR) and Fourier transform infrared spectroscopy (FT-IR). Thermal analysis of all reactive systems are also performed and studied by differential scanning calorimetry (DSC). The introduction of S8 into benzoxazines generates a new structure bearing a Schiff base and a phenolic -OH within the reactive system, which then triggers the reduction of the polymerization temperature in about 15% when as low as 5 mol% of S8 is added.
- Arza, Carlos Rodriguez,Froimowicz, Pablo,Ishida, Hatsuo
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p. 35144 - 35151
(2016/05/19)
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- Ruthenium (II) complexes of NO ligands: Synthesis, characterization and application in transfer hydrogenation of carbonyl compounds
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New Schiff base ligands including azo group such as (4-((E)-(4-ethylphenyl)diazenyl)-2-((E)-(phenylimino)methyl)phenol 2, 4-((E)-(4-ethylphenyl)diazenyl)-2-((E)-(naphthalen-1-ylimino)methyl)phenol 3, 2-((E)-(benzylimino)methyl)-4-((E)-(4-ethylphenyl)diazenyl)phenol 4 and azo group-free ligand (E)-2-((benzylimino)methyl)phenol 8 and their ruthenium complexes 5-7 and 9 with [RuCl2(p-cymene)] were synthesized and characterized by spectroscopic techniques including 1H and 13C NMR, FT-IR and UV-Vis. According to the UV-visible, IR and NMR data, the Ru (II) complexes 5-7 and 9 are formed by the coordination of N, O atoms of the ligands. Molecular structures of the complex 7 and complex 9 were determined by single crystal X-ray diffraction studies. These Ruthenium (II) complexes 5-7 and 9 were used as catalysts for the transfer hydrogenation of a series of ketones and benzaldehyde in 2-propanol. Following the comparison of complex 9 with the other three azo containing complexes 5-7, it was observed that azo group has got remarkable increasing effect on the catalytic activity. The results showed that the complex 5 is efficient than the other Ru (II) complexes.
- ?alik, Hatice Selvi,Ispir, Esin,Karabuga, ?emistan,Aslantas, Mehtet
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p. 122 - 129
(2015/11/18)
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- Efficient one-pot synthesis of trans-Pt(ii)(salicylaldimine)(4-picoline)Cl complexes: Effective agents for enhanced expression of p53 tumor suppressor genes
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A series of trans-Pt(ii)(salicylaldimine)(4-picoline)Cl complexes were synthesized in 78-87% yield using a one-pot procedure from commercially available precursors. The structures of these complexes were characterized by 1H, 19F and
- Rahman, Faiz-Ur,Ali, Amjad,Guo, Rong,Wang, Wei-Kun,Wang, Hui,Li, Zhan-Ting,Lin, Yuejian,Zhang, Dan-Wei
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supporting information
p. 9872 - 9880
(2015/06/02)
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- Metal and ligand-substituent effects in the immortal polymerization of rac -lactide with Li, Na, and K phenoxo-imine complexes
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A series of lithium, sodium, and potassium complexes with phenoxo-imine ligands M[(O-2-(RN=CH)C6H4] [R = C6H5; 2-tBuC6H5; 2,6-iPr2C6H3
- Garca-Valle, Francisco M.,Estivill, Robert,Gallegos, Carlos,Cuenca, Toms,Mosquera, Marta E. G.,Tabernero, Vanessa,Cano, Jess
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p. 477 - 487
(2015/02/05)
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- Selectively catalytic epoxidation of α-pinene with dry air over the composite catalysts of Co-MOR(L) with Schiff-base ligands
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Twelve bi-/tridentate Schiff-base ligands (L1-L12) have been designed, synthesized and coordinated with ion-exchanged Co-MOR (Mordenite) forming a series of Co-MOR(L) composite catalysts, for which various analyzes and characterizations are conducted. Selectively catalytic epoxidation of α-pinene with dry air over Co-MOR(L) catalysts has been carried out, where uses TBHP in small amounts as the initiator. Among these Co-MOR(L) catalysts, Co-MOR(L8) exhibits the best activity for the titled reaction to obtain 85.8 mol% conversion and 90.8% selectivity of epoxide. Some factors such as the structure of ligands, the oxidants, the solvents, the catalyst amount, the reaction temperature and time play important roles in controlling the epoxidation. The recyclable stability of the Co-MOR(L8) catalyst is confirmed. The studies on the electrochemical behaviors of Co species in Co-MOR(L8) reveal the importance of reversible change between Co oxidation states for the epoxidation.
- Lu,Lei,Wei,Ma,Zhang,Hu,Zhou,Xia
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- Experimental and theoretical study of antioxidative properties of some salicylaldehyde and vanillic Schiff bases
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The antioxidative capacity and structure-activity relationships of ten Schiff bases were investigated experimentally and theoretically. All compounds contain the aniline moiety, while the aldehyde part is either salicylaldehyde or vanillin. The DPPH assay was used to test the potential antioxidative activity of these compounds, and DFT study was used to investigate their electronic structures and provide insight into their structure-activity relationships. The effect of the position of the hydroxy, as well other groups present, on the antioxidative activity was examined. The possible radical scavenging mechanism was determined in polar (water and methanol), and nonpolar (benzene) solvents. Based on the experimental and computational results, compounds 7 and 8 exhibit the highest radical scavenging properties.
- Petrovi?, Zorica D.,Orovi?, Jelena,Simijonovi?, Du?ica,Petrovi?, Vladimir P.,Markovi?, Zoran
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p. 24094 - 24100
(2015/03/30)
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