788-24-9Relevant academic research and scientific papers
Structure and Photochemistry of N-Salicylidene-p-carboxyaniline Isolated in Solid Argon
Avadanei, Mihaela,Ku?, Nihal,Cozan, Vasile,Fausto, Rui
, p. 9121 - 9132 (2015)
Infrared matrix isolation spectroscopy and DFT/B3LYP/6-311++G(d,p) calculations have been used to characterize the conformational space of the enol-imine and keto-amine tautomers of N-salicylidene-p-carboxyaniline (SCA) in both their E and Z isomeric forms. Monomers of SCA were isolated in an argon matrix (15 K), which was shown to contain only the most stable conformer of the E-enol isomer of the compound. The matrix-isolated E-enol was then subjected to in situ UV irradiation (λ = 335; 345 nm, provided by a laser/MOPO system, or λ > 235 nm, provided by a Hg(Xe) broad-band source), and the photoinduced processes probed by infrared spectroscopy. Two photoreaction channels were observed, with a branching ratio of ~1:1, corresponding to E-enol → Z-enol isomerization and E-enol → E-keto tautomerization. Both processes were found to be rather effective, with practically complete consumption of the reactant after broad-band irradiation by 1 min only. Identification among the photoproduced species of the Z-enol conformer that differs from the reactant only by E-to-Z isomerization suggests the initial photoproduction of this conformer, which subsequently decays into the lowest energy Z-enol conformer (also identified experimentally). The E-enol → E-keto tautomerization requires an excited state intramolecular proton transfer and twisting about the exocyclic CC bond of the molecule. These processes most probably take place sequentially. However, in the present study the Z-keto isomer, which should act as intermediate in this sequence of processes, could not be detected, most probably due to its short lifetime under the used experimental conditions. On the contrary, the detailed structural and vibrational characterization of the photoproduced E-keto form was successfully achieved. (Figure Presented).
Development of an off-on selective fluorescent sensor for the detection of Fe3+ ions based on Schiff base and its Hirshfeld surface and DFT studies
Singh, Gurpreet,Sindhu, Jayant,Manisha,Kumar, Vinod,Sharma, Vishal,Sharma, Suresh Kumar,Mehta, Surinder Kumar,Mahnashi, Mater H.,Umar, Ahmad,Kataria, Ramesh
, (2019)
Herein, a Schiff base, 4-(2-hydroxybenzylideneamino) benzoic acid (HBBA) was synthesized and characterized by FT-IR, 1H NMR and single crystal X-ray. The geometrical parameters calculated for the structure prepared using DFT methods were in clo
Catena-Poly[[[pyridine-copper(II)]bis-[μ3-4-(2-oxidobenzyl- ideneamino)-benzoato]] dimethyl-formamide disolvate], a polymer composed of dimeric dicopper building units
Ni, Qing-Ling,Li, Fa-Si,Wang, Xiu-Jian,Bi, Xian-Su,Liao, Sen
, p. m416-m418 (2007)
The title compound, {[Cu(C14H9NO3)(C5H5N)]·C3H7NO} n or {[Cu2 L 2(py)2]·2DMF} n [py is pyridine, L is 4-(salicylidene-amino)benzoate and DMF is dimethyl-formamide], is composed of dimeric dicopper [CuL(py)]2 building units, which are inter-linked into a o
Mechanochemistry in action: Exploitation of internal acid catalysis in Solvent-free synthesis of imines and evaluation of radical scavenging activities of imino derivatives
Sarma, Madhushree Das,Ghosh, Subhojit
, p. 345 - 349 (2021/02/02)
Mechanochemical protocol has been exploited to accomplish the synthesis of imino derivatives from aromatic amines with acidic functionalities and different aromatic aldehydes in excellent to nearly quantitative yields. Presence of acidic groups in the aromatic amines has been found to have profound influence on the course of the reaction. The prepared imines were screened for in vitro antioxidant activity using 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical. Some of the prepared imino derivatives displayed good to moderate antioxidant property when compared with standard natural antioxidant (L-ascorbic acid).
Novel Schiff base DOPO phosphorus-nitrogen flame retardant as well as synthesis method and application thereof
-
Paragraph 0037-0039; 0044-0046; 0048-0050, (2021/10/05)
The invention discloses a novel Schiff base DOPO phosphorus-nitrogen flame retardant, and the structural formula is as follows. The flame retardant uses salicylaldehyde. The corresponding Schiff base is synthesized from p-aminobenzoic acid, and then react
4-aminobenzoic acid derivatives: Converting folate precursor to antimicrobial and cytotoxic agents
Brablíková, Michaela,Jan?ourek, Ond?ej,Janou?ek, Ji?í,Kone?ná, Klára,Krátky, Martin,Stola?íková, Ji?ina,Trejtnar, Franti?ek,Vin?ová, Jarmila
, (2020/01/25)
4-aminobenzoic acid (PABA), an essential nutrient for many human pathogens, but dispensable for humans, and its derivatives have exhibited various biological activities. In this study, we combined two pharmacophores using a molecular hybridization approach: this vitamin-like molecule and various aromatic aldehydes, including salicylaldehydes and 5-nitrofurfural, via imine bond in one-step reaction. Resulting Schiff bases were screened as potential antimicrobial and cytotoxic agents. The simple chemical modification of non-toxic PABA resulted in constitution of antibacterial activity including inhibition of methicillin-resistant Staphylococcus aureus (minimum inhibitory concentrations, MIC, from 15.62 μM), moderate antimycobacterial activity (MIC ≥ 62.5 μM) and potent broad-spectrum antifungal properties (MIC of ≥ 7.81 μM). Some of the Schiff bases also exhibited notable cytotoxicity for cancer HepG2 cell line (IC50 ≥ 15.0 μM). Regarding aldehyde used for the derivatization of PABA, it is possible to tune up the particular activities and obtain derivatives with promising bioactivities.
Schiff base synthesis as a capping agent for green synthesized silver nanoparticles
Almashal,Al-Abdullah,Jassem
, p. 813 - 821 (2020/04/17)
A SCHIFF base 3 was synthesized and used as a new capping agent for synthesis of silver nanoparticles through preventing overgrowth of silver oxide. Schiff base 3 helps to enhance the structural properties of the resulted silver nanoparticles in a disting
Catalytic isomerization-hydroformylation of olefins by rhodium salicylaldimine pre-catalysts
Sekoto, Pamela N.,Magengenene, Tseliso M.,Matsinha, Leah C.,Tia, Richard,Darkwa, James,Makhubela, Banothile C. E.
, p. 8751 - 8762 (2020/06/08)
A series of new Schiff-base rhodium(i) water-soluble complexes (C1-C3), were prepared and characterized. These complexes served as catalyst precursors for the hydroformylation of 1-octene and resulted in excellent substrate conversions (>98%) with 100% chemoselectivities to aldehydes, under mild conditions. Notably, good regioselectivities towards branched aldehydes were observed clearly demonstrating the catalysts’ ability in thermodynamically favoured isomerization followed by hydroformylation (n/iso ratio ranging between 0.7-1.2). Interestingly, catalystC1uniquely promoted contra-thermodynamic isomerization of 2-octene to 1-octene with up to 50% conversion. The efficacy of catalystC1was further evaluated in the hydroformylation of longer chain olefins (C10-C12), methyl acrylate, ethyl acrylate and styrene. The catalyst displayed conversions >99% with the long chain substrates and much lower conversions with the acrylates. These water-soluble (pre)catalysts were recycled up to three times with no significant loss in catalytic activity and selectivity. Mercury poisoning tests were conducted and the experiments revealed that the conversion of the substrates into aldehydes was due to molecular active catalysts and not as a result of colloidal particles that could have formedin situthrough the decomposition of the catalyst precursor. Finally, the molecular catalyst responsible for activity was established using preliminary computational calculations.
Strategic modification of ligands for remarkable piezochromic luminescence (PCL) based on a neutral Ir(iii) phosphor
Li, Dan,Li, Guangfu,Xie, Jiaxin,Zhu, Dongxia,Su, Zhongmin,Bryce, Martin R.
supporting information, p. 10876 - 10880 (2019/09/19)
A new aggregation-induced emission (AIE)-active neutral Ir(iii) complex has been rationally designed and synthesized by introducing carboxyl and F substituents into the ancillary and cyclometalating ligands, respectively, to construct different kinds of i
Design, synthesis and evaluation of some N-methylenebenzenamine derivatives as selective acetylcholinesterase (AChE) inhibitor and antioxidant to enhance learning and memory
Shrivastava, Sushant K.,Srivastava, Pavan,Upendra,Tripathi, Prabhash Nath,Sinha, Saurabh K.
, p. 1471 - 1480 (2017/02/10)
Series of some 3,5-dimethoxy-N-methylenebenzenamine and 4-(methyleneamino)benzoic acid derivatives comprising of N-methylenebenzenamine nucleus were designed, synthesized, characterized, and assessed for their acetylcholinesterase (AChE), butyrylcholinesterase (BChE) inhibitory, and antioxidant activity thereby improving learning and memory in rats. The IC50values of all the compound along with standard were determined on AChE and BChE enzyme. The free radical scavenging activity was also assessed by in vitro DPPH (2,2-diphenyl-1-picryl-hydrazyl) and hydrogen peroxide radical scavenging assay. The selective inhibitions of all compounds were observed against AChE in comparison with standard donepezil. The enzyme kinetic study of the most active compound 4 indicated uncompetitive AChE inhibition. The docking studies of compound 4 exhibited the worthy interaction on active-site gorge residues Phe330 and Trp279 responsible for its high affinity towards AChE, whereas lacking of the BChE inhibition was observed due to a wider gorge binding site and absence of important aromatic amino acids interactions. The ex vivo study confirmed AChE inhibition abilities of compound 4 at brain site. Further, a considerable decrease in escape latency period of the compound was observed in comparison with standard donepezil through in vivo Spatial Reference Memory (SRM) and Spatial Working Memory (SWM) models which showed the cognition-enhancing potential of compound 4. The in vivo reduced glutathione (GSH) estimation on rat brain tissue homogenate was also performed to evaluate free radical scavenging activity substantiated the antioxidant activity in learning and memory.
