623-26-7Relevant academic research and scientific papers
Solvent effects in simple fast electron transfer reactions
Winkler, Krzysztof,Baranski, Andrzej S.,Fawcett, W. Ronald
, p. 3899 - 3904 (1996)
The kinetics of the one-electron reduction of p-dicyanobenzene and the oxidation of nickelocene have been studied by ac voltammetry in different aprotic solvents at mercury and platinum ultramicroelectrodes. The observed electron transfer rate constants have been corrected for the double-layer effect. The solvent dependences of the electron transfer rate constants and activation enthalpy are interpreted within the context of contemporary theory. The charge transfer process was found to be perfectly adiabatic for both studied systems. Solvent dynamic and Gibbs activation energy effects on the rate constants were also investigated.
The self-assembly and metal adatom coordination of a linear bis-tetrazole ligand on Ag(111)
Knecht, Peter,Suryadevara, Nithin,Zhang, Bodong,Reichert, Joachim,Ruben, Mario,Barth, Johannes V.,Klyatskaya, Svetlana,Papageorgiou, Anthoula C.
, p. 10072 - 10075 (2018)
We employ a linear linker molecule consisting of a benzene functionalised with two tetrazole moieties at para positions. Its self-assembly and coordination with the native silver adatoms and codeposited Fe adatoms on a Ag(111) surface under ultra high vacuum conditions are investigated by means of scanning tunnelling microscopy and X-ray photoelectron spectroscopy. We discover a rich spectrum of room-temperature stable Ag and Fe2+ coordination nodes depending on the formation temperature.
Electrochemically Catalyzed Aromatic Nucleophilic Substitution. Reactivity of Cyanide Ions toward Aryl Radicals in Liquid Ammonia
Amatore, Christian,Combellas, Catherine,Robveille, Sabine,Saveant, Jean-Michel,Thiebault, Andre
, p. 4754 - 4760 (1986)
The mechanism of the substitution of a series of aromatic halides by cyanide ion under electrochemical induction is described as a function of the substrate.The rate constants of the addition of cyanide ion on eight aryl radicals have been determined by using either a direct or a competitive electrochemical method.The variation of the reactivity toward the CN- ions with the structure of the aryl radicals is discussed.
Synthesis, Biological Activity, and Molecular Docking Assessment of Some New Sulfonylated Tetrazole Derivatives
Arshad,Khan,Nami
, p. 1851 - 1858 (2019)
The designed molecular structures have been subjected to computational analysis for calculating their physicochemical properties and drug likeness. The calculated data indicate that most of the compound possess the bioactivity score in the active zone. Synthetic approach to the target compounds is straightforward and easy to handle. Structures of the new compounds are supported by FT-IR, 1H, and 13C NMR, and mass spectra. Antimicrobial tests of the products against pathogens (S. aureus, S. epidermidis, E. coli, and P. mirabilis) indicate the products as active or highly active. Their cyto-toxicity is determined to be 92–98% at concentration of 3.125 μmol/L. The molecular docking analysis carried out for the target compounds against the receptor Glc-N-6P exhibits low binding energy and various binding sites of those.
Synthesis, Characterization, and Catalytic Study of Caffeine-Derived N-heterocyclic Carbene Palladium Complexes
Chen, Haiqun,Huynh, Han Vinh,Liu, Ziwei,Lu, Yuchen,Meng, Qi,Teng, Qiaoqiao,Yuan, Dan,Zhao, Yaru
, p. 161 - 168 (2022/02/07)
Homo- and heterodicarbene palladium complexes bearing caffeine-derived N-heterocyclic carbene ligands were synthesized and fully characterized by NMR spectroscopy, mass spectrometry, and X-ray diffraction analysis. The superior acidity of the alkylated ca
Nitrile Synthesis via Desulfonylative-Smiles Rearrangement
Abe, Masahiro,Nitta, Sayasa,Miura, Erina,Kimachi, Tetsutaro,Inamoto, Kiyofumi
, p. 4460 - 4467 (2022/03/15)
Herein, we designed a simple nitrile synthesis from N-[(2-nitrophenyl)sulfonyl]benzamides via base-promoted intramolecular nucleophilic aromatic substitution. The process features redox-neutral conditions as well as no requirement of toxic cyanide species and transition metals. Our process shows broad scope and various functional group compatibility, affording a variety of (hetero)aromatic nitriles in good to excellent yields.
Water-Dispersible Pd–N-Heterocyclic Carbene Complex Immobilized on Magnetic Nanoparticles as a New Heterogeneous Catalyst for Fluoride-Free Hiyama, Suzuki–Miyaura and Cyanation Reactions in Aqueous Media
Chahkamali, Farhad Omarzehi,Sansano, José Miguel,Sobhani, Sara
, (2021/11/10)
Abstract: Pd–N-heterocyclic carbine complex immobilized on magnetic nanoparticles is synthesized and characterized by different techniques such as FT-IR, XPS, TEM, EDX, FESEM, VSM, TGA, and ICP. The synthesized catalyst was used as a new water dispersible heterogeneous catalyst in the fluoride-free Hiyama, Suzuki–Miyaura and cyanation reactions in pure water. By this method, different types of biaryls and aryl nitriles were synthesized in good to high yields by the reaction of a variety of aryl iodides, bromides and chlorides with triethoxyphenylsilane, phenylboronic acid and K4[Fe(CN)6]·3H2O, respectively. The presence of sulfonates as hydrophilic groups on the surface of the catalyst confers a highly water dispersible, active and yet magnetically recoverable Pd catalyst. The possibility to perform the reaction in water as a green medium, ease of the catalyst recovery and reuse by magnetic separation, and the absence of any additives or co-solvents make this method as an eco-friendly and economical protocol for the synthesis of biaryl derivatives and aryl nitriles. Graphic Abstract: A new water dispersible heterogeneous Pd–N-heterocyclic carbene for the efficient fluoride-free Hiyama, Suzuki–Miyaura and cyanation reactions in pure water is developed.[Figure not available: see fulltext.].
Copper-Catalyzed One-Pot Synthesis of Quinazolinones from 2-Nitrobenzaldehydes with Aldehydes: Application toward the Synthesis of Natural Products
Pal, Shantanu,Sahoo, Subrata
, p. 18067 - 18080 (2021/12/06)
A novel, efficient, and atom-economical approach for the construction of quinazolinones from 2-nitrobenzaldehydes has been unveiled via copper-catalyzed nitrile formation, hydrolysis, and reduction in one pot for the first time. In this reaction, urea is used as a source of nitrogen for nitrile formation, hydrazine hydrate is used for both the reduction of the nitro group and the hydrolysis of nitrile, and atmospheric oxygen is used as the sole oxidant. The method portrays a wide substrate scope with good functional group tolerances. Moreover, this method was applied for the synthesis of schizocommunin, tryptanthrin, phaitanthrin-A, phaitanthrin-B, and 8H-quinazolino[4,3-b]quinazolin-8-one.
A Molecular Iron-Based System for Divergent Bond Activation: Controlling the Reactivity of Aldehydes
Chatterjee, Basujit,Jena, Soumyashree,Chugh, Vishal,Weyhermüller, Thomas,Werlé, Christophe
, p. 7176 - 7185 (2021/06/30)
The direct synthesis of amides and nitriles from readily available aldehyde precursors provides access to functional groups of major synthetic utility. To date, most reliable catalytic methods have typically been optimized to supply one product exclusively. Herein, we describe an approach centered on an operationally simple iron-based system that, depending on the reaction conditions, selectively addresses either the C=O or C-H bond of aldehydes. This way, two divergent reaction pathways can be opened to furnish both products in high yields and selectivities under mild reaction conditions. The catalyst system takes advantage of iron's dual reactivity capable of acting as (1) a Lewis acid and (2) a nitrene transfer platform to govern the aldehyde building block. The present transformation offers a rare control over the selectivity on the basis of the iron system's ionic nature. This approach expands the repertoire of protocols for amide and nitrile synthesis and shows that fine adjustments of the catalyst system's molecular environment can supply control over bond activation processes, thus providing easy access to various products from primary building blocks.
Facile dehydration of primary amides to nitriles catalyzed by lead salts: The anionic ligand matters
Ruan, Shixiang,Ruan, Jiancheng,Chen, Xinzhi,Zhou, Shaodong
, (2020/12/09)
The synthesis of nitrile under mild conditions was achieved via dehydration of primary amide using lead salts as catalyst. The reaction processes were intensified by not only adding surfactant but also continuously removing the only by-product, water from the system. Both aliphatic and aromatic nitriles can be prepared in this manner with moderate to excellent yields. The reaction mechanisms were obtained with high-level quantum chemical calculations, and the crucial role the anionic ligand plays in the transformations were revealed.
