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Journal articles on the topic 'Aluminium(I) Nucleophile'

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Author: Grafiati
Published: 10 December 2022
Last updated: 29 January 2023

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1

Hinz, Alexander, and Frank Breher. "An Anionic Aluminium Nucleophile." Angewandte Chemie International Edition 57, no. 29 (June 14, 2018): 8818–20. http://dx.doi.org/10.1002/anie.201804930.

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2

Nishi, Takafumi, Isao Mizota, and Makoto Shimizu. "Integrated reactions using addition to conjugated imines and iminium salts." Pure and Applied Chemistry 84, no. 12 (June 30, 2012): 2609–17. http://dx.doi.org/10.1351/pac-con-12-01-03.

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Recently, nucleophilic addition reactions to imino functions have been utilized in many crucial steps for the synthesis of bioactive and functional materials. This article summarizes the integrated “umpolung” reactions of α-imino esters and the use of iminium salts as reactive electrophiles. Regarding the umpolung reactions, the following five reactions are discussed: (1) N-alkylation/homocoupling; (2) tandem N-ethylation/C-allylation; (3) tandem N-ethylation/C-cyanation; (4) reduction of imines with tris(trimethylsilyl)aluminum; and (5) N-alkylation and Claisen rearrangement. Moreover, the generation and reactions of alkoxycarbonyl iminium species are also discussed. These are prepared easily from trisubstituted amino ketene silyl acetals by oxidation, and the subsequent nucleophilic addition of various nucleophiles readily affords the addition products.
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3

Zhang, Zhichao, Tianming Wang, Peng Xiang, Qinqin Du, and Shuang Han. "Syntheses, Characterization, and Application of Tridentate Phenoxyimino-Phenoxy Aluminum Complexes for the Coupling of Terminal Epoxide with CO2: From Binary System to Single Component Catalyst." Catalysts 11, no. 2 (January 20, 2021): 145. http://dx.doi.org/10.3390/catal11020145.

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A series of binuclear aluminum complexes 1–3 supported by tridentate phenoxyimino-phenoxy ligands was synthesized and used as catalysts for the coupling reaction of terminal epoxide with carbon dioxide. The aluminum complex 1, which is catalytically inactive toward the coupling of epoxide with CO2 by itself, shows moderate activity in the presence of excess nucleophiles or organic bases at high temperature. In sharp contrast to complex 1, bifunctional complexes 2 and 3, which incorporate tertiary amine groups as the built-in nucleophile, are able to efficiently transform terminal epoxide with CO2 to corresponding cyclic carbonates as a sole product by themselves at 100 °C. The number of amine groups on the ligand skeleton and the reaction temperature exert a great influence on the catalytic activity. The bifunctional complexes 2 and 3 are also active at low carbon dioxide pressure such as 2 atm or atmospheric CO2 pressure. Kinetic studies of the coupling reactions of chloropropylene oxide/CO2 and styrene oxide/CO2 using bifunctional catalysts under atmospheric pressure of CO2 demonstrate that the coupling reaction has a first-order dependence on the concentration of the epoxide.
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4

Cheng, Xu, Shuchen Pei, Chenchen Xue, Kaifei Cao, Li Hai, and Yong Wu. "Reactions of β-diketone compounds with nitriles catalyzed by Lewis acids: a simple approach to β-enaminone synthesis." RSC Adv. 4, no. 109 (2014): 63897–900. http://dx.doi.org/10.1039/c4ra10879e.

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5

Konshin, Valery V., Vitaly A. Shcherbinin, Ida A. Lupanova, and Dzhamilya N. Konshina. "Aluminum Triflate—Catalyzed Adamantylation of N-Nucleophiles." Proceedings 9, no. 1 (November 14, 2018): 21. http://dx.doi.org/10.3390/ecsoc-22-05661.

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An efficient method is proposed for N-adamantylation of primary carboxamides and sulfonamides, ethyl carbamate, and 4-nitroaniline using the stoichiometric amount of 1-adamantanol in the presence of 5 mol% aluminum triflate in nitromethane. Similarities and differences between adamantylation of some azoles catalyzed by aluminum triflate in nitromethane and the reaction catalyzed by Brønsted acids were revealed.
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6

Yamashita, Makoto. "Characteristic Reactions of Nucleophilic Aluminum Anion." Journal of Synthetic Organic Chemistry, Japan 79, no. 5 (May 1, 2021): 457–64. http://dx.doi.org/10.5059/yukigoseikyokaishi.79.457.

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7

Ranishenka, B. V., I. A. Chelnokova, and A. A. Poznyak. "Aluminium and mica azide surface functionalization." Proceedings of the National Academy of Sciences of Belarus, Chemical Series 58, no. 4 (November 29, 2022): 379–86. http://dx.doi.org/10.29235/1561-8331-2022-58-4-379-386.

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Aluminium and mica (muscovite) plates have been functionalized with azide groups by a protocol which includes (3-chloropropyl) trichlorosilane modification followed by chlorine atom nucleophilic substitution by azide. The azide groups have been transformed to dimethoxytrityl (DMT) ones by [3+2] azide-alkyne cycloaddition reaction. This made it possible to determine their number per surface unit photometrically, based on the absorption of the DMT cation. The functionalization method allowed to achieve high surface load of the materials by azide groups, which was 2.2 and 2.7 nm-2 for mica and aluminium, respectively. The mica plates have been additionally functionalized by 25 kDa branched polyethylenimine. The samples have shown a capability for adsorptive nanoand microobjects immobilization. The feature could be useful for atomic force microscopy, which have been demonstrated with erythrocytes and exosomes.
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8

Esrafili, Mehdi D. "A DFT study on electronic structure and local reactivity descriptors of pristine and carbon-substituted AlN nanotubes." Canadian Journal of Chemistry 91, no. 8 (August 2013): 711–17. http://dx.doi.org/10.1139/cjc-2013-0103.

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A density functional theory study was carried out to investigate the structural and electronic structure properties of pristine and carbon-substituted (6,0) aluminum nitride nanotubes (AlNNTs). We examine the usefulness of local reactivity descriptors to predict the reactivity of AlN atomic sites on the external surface of the tubes. The properties determined include the Fukui function f(k) and local softness s(k) on the surfaces of the investigated tubes. According to the values of f(k) and s(k) for the pristine AlNNT, the aluminum atoms are highly preferred sites for nucleophile addition. More especially, the aluminum atoms in middle portion show different reactivity pattern from those at the edge or cap regions of the nanotube. Our results indicate that the nitrogen atoms adjacent to the substituted carbon atoms are less reactive toward atomic hydrogen chemisorption than those in the pristine one. There is an acceptable correlation between chemisorption energies and reactivity indexes, indicating that f(k) and s(k) provide an effective means for rapidly and economically assessing the relative reactivities of finite-sized AlNNTs.
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9

Cullen, Adam, Alfred J. Muller, and D. Bradley G. Williams. "Protecting group-free use of alcohols as carbon electrophiles in atom efficient aluminium triflate-catalysed dehydrative nucleophilic displacement reactions." RSC Advances 7, no. 67 (2017): 42168–71. http://dx.doi.org/10.1039/c7ra08784e.

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10

Kasal, Alexander, and Jaroslav Zajíček. "Solvolysis of Westphalen-type compounds." Collection of Czechoslovak Chemical Communications 51, no. 7 (1986): 1462–75. http://dx.doi.org/10.1135/cccc19861462.

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Action of some nucleophilic reagents (CH3COOAg, CH3COOK, LiAlH4) on 6β-chloro- and 6β-methanesulfonyloxy-5-methyl-19-nor-5β-cholest-9-enes VIII - XII affords predominantly A-homo-B,19-dinor-5β-cholest-9-ene derivatives, arising by rearrangement and substitution (XIII, XXIV) or rearrangement and elimination (e.g. XX). Hydrogenolysis of compounds of the type VIII with lithium aluminium hydride gives, in addition, a product of rearrangement, fragmentation and further reduction (XXVI), and 5-methyl-6α,10-cyclo-19-nor-5β,9β,10α-cholestan-3β-ol (XXX).
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11

Veselý, Ivan, and Václav Dědek. "Reactivity of 2,2-difluoro-3-methyl-3-butenal toward some O-, N- and C-nucleophiles." Collection of Czechoslovak Chemical Communications 50, no. 12 (1985): 2730–42. http://dx.doi.org/10.1135/cccc19852730.

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Addition of nucleophiles to 2,2-difluoro-3-methyl-3-butenal (I) is complicated by its spontaneous polymerization. Compound I afforded neither hydrate nor dimethyl acetal but reacted with ethylene glycol to give the cyclic acetal II. Reaction with acetyl chloride and acetic anhydride led to the respective acetate III and diacetate IV. Satisfactory reaction with N-nucleophiles was observed only in the case of hydroxylamine and dinitrophenylhydrazine. Diethylamine reacted with I only at 150 °C to give the reduction product VI and the ethylaldimine VII. The compound I added nitromethane and sodium cyanide (giving X and XI, respectively); the adducts or products of their reduction with lithium aluminium hydride were hydroxylated at the double bond to give analogues of alcoholic sugars with difluoromethylene group in position 3. Hydroxylation of the butenal I or the acetate III afforded 3,3-difluoro-2,4-dihydroxy-4-methyloxolane (XIX) which was prepared also by cleavage of the acetal XVIII obtained from II by hydroxylation. Addition of bromine to the double bond in III and IV gave the dibromo derivatives XV and XVI; the attempted replacement of bromine in XV and XVI by acetate anion failed. Bromination of I in aqueous medium afforded 3-bromo-2,2-difluoro-3-methyl-4-butanolide (XIV).
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12

Mesías-Salazar, Ángela, Yersica Rios Yepes, Javier Martínez, and René S. Rojas. "Highly Active CO2 Fixation into Cyclic Carbonates Catalyzed by Tetranuclear Aluminum Benzodiimidazole-Diylidene Adducts." Catalysts 11, no. 1 (December 22, 2020): 2. http://dx.doi.org/10.3390/catal11010002.

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A set of tetranuclear alkyl aluminum adducts 1 and 2 supported by benzodiimidazole-diylidene ligands L1, N,N’-(1,5-diisopropylbenzodiimidazole-2,6-diylidene)bis(propan-2-amine), and L2, N,N’-(1,5-dicyclohexyl-benzodiimidazole-2,6-diylidene)dicyclohexanamine were synthetized in exceptional yields and characterized by spectroscopic methods. These compounds were studied as catalysts for cyclic carbonate formation (3a–o) from their corresponding terminal epoxides (2a–o) and carbon dioxide utilizing tetrabutylammonium iodide as a nucleophile in the absence of a solvent. The experiments were carried out at 70 °C and 1 bar CO2 pressure for 24 h and adduct 1 was the most efficient catalyst for the synthesis of a large variety of monosubstituted cyclic carbonates with excellent conversions and yields.
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13

Deora, Nipa, and Paul R. Carlier. "A computational study of regioselectivity in aluminum hydride ring-opening of cis- and trans-4-t-butyl and 3-methylcyclohexene oxides." Organic & Biomolecular Chemistry 17, no. 37 (2019): 8628–35. http://dx.doi.org/10.1039/c9ob01675a.

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14

Wong, C. M., P. M. Gordon, A. G. Chen, and H. Y. P. Lam. "The total synthesis of (±)-4-demethoxy-10-nordaunomycinone." Canadian Journal of Chemistry 65, no. 6 (June 1, 1987): 1375–79. http://dx.doi.org/10.1139/v87-232.

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4-Demethoxy-10-nordaunomycinone (4) is synthesized starting with 4,7-dimethoxy-1-indanone (8). Nucleophilic addition of ethynyl magnesium bromide to 8 followed by mercuric acetate oxidation and iron pentacarbonyl – tri-n-butyltin hydride reduction gave 4,7-dimethoxy-1-acetylindane (16). Condensation of 16 with phthalic anhydride followed by methylation with dimethylsulfate and oxidation gave 22, which was epimerized to 24 by 2,2-dimethoxypropane and trifluoroacetic acid. Demethylation of 24 with aluminum chloride gave the 4-demethoxy-10-nordaunomycinone (4).
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15

Erb, William, Florence Mongin, Nahida Brikci-Nigassa, and Ghenia Bentabed-Ababsa. "In Situ ‘Trans-Metal Trapping’: An Efficient Way to Extend the Scope of Aromatic Deprotometalation." Synthesis 50, no. 18 (March 8, 2018): 3615–33. http://dx.doi.org/10.1055/s-0036-1591953.

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Deprotometalation is an efficient method to functionalize regioselectively aromatic compounds including heterocycles. This short review shows how it is possible to intercept aryllithiums (and other polar arylmetals) as soon as they are formed by in situ ‘trans-metal trapping’. The approach avoids long contact between aryllithiums and sensitive substrates. In addition, it allows less activated substrates to be deprotonated by non-nucleophilic lithium amides. While using chloro­silanes and borates still arouses the interest of chemists, more recently, methods based on zinc, aluminum and gallium have appeared, enabling this chemistry to grow dramatically.1 Introduction2 Silicon-Based In Situ Traps3 Boron-Based In Situ Traps4 Zinc-Based In Situ Traps5 Aluminum- and Gallium-Based In Situ Traps6 Other In Situ Traps7 Continuous-Flow In Situ ‘Trans-Metal Trapping’8 Conclusion
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16

Saito, Susumu, Toshihiko Sone, Masaaki Murase, and Hisashi Yamamoto. "Aluminum Tris(2,6-diphenylphenoxide)-ArCOCl Complex for Nucleophilic Dearomatic Functionalization." Journal of the American Chemical Society 122, no. 41 (October 2000): 10216–17. http://dx.doi.org/10.1021/ja0014382.

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17

Harder, Sjoerd, and Jan Spielmann. "Unprecedented reactivity of an aluminium hydride complex with ArNH2BH3: nucleophilic substitution versus deprotonation." Chemical Communications 47, no. 43 (2011): 11945. http://dx.doi.org/10.1039/c1cc14689k.

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18

Saito, Susumu, Toshihiko Sone, Masaaki Murase, and Hisashi Yamamoto. "ChemInform Abstract: Aluminum Tris(2,6-diphenylphenoxide)-ArCOCl Complex for Nucleophilic Dearomatic Functionalization." ChemInform 32, no. 7 (May 30, 2010): no. http://dx.doi.org/10.1002/chin.200107075.

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19

Sudhakar, Kolanu, Atif Mahammed, Natalia Fridman, and Zeev Gross. "Iodinated cobalt corroles." Journal of Porphyrins and Phthalocyanines 21, no. 12 (December 2017): 900–907. http://dx.doi.org/10.1142/s108842461750095x.

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Cobalt(III) complexes of selectively [Formula: see text]-pyrrole-iodinated corroles were prepared and characterized for the first time. X-ray crystallographic data reveals that the corrole macrocycle remains quite planar despite of the presence of multiple iodine substituents. The redox potentials increase linearly with the number of iodine substituents, much more for reduction than for oxidation, in a similar pattern to that of previously reported gold(III), gallium(III), and aluminum(III) complexes of [Formula: see text]-pyrrole-iodinated corroles. Their effect on reduction potential is much larger than what is observed for analogous gallium(III) and aluminum(III) corroles, wherein the chelated element is not redox active. Interestingly, the effect of iodine is similar to that of the much more electronegative halides, which is attributed to a stronger [Formula: see text]-back donation by the latter. One advantage of achieving selective iodination, in terms of the number and positioning, is that is provides an entry to further functionalization of the corrole skeleton via nucleophilic aromatic substitution.
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20

Colby, David, Francis Barrios, Brannon Springer, and Robert Hazlitt. "Effect of Substituents and Stability of Transient Aluminum–Aminals­ in the Presence of Nucleophiles." Synthesis 47, no. 02 (December 5, 2014): 175–80. http://dx.doi.org/10.1055/s-0034-1379635.

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21

El-Samahy, Fatma A. "A stereochemical investigation of the nucleophilic addition of methyl ethyl ketone to (E)-alkyloxindolylideneacetates." Journal of Chemical Research 2005, no. 1 (January 2005): 62–66. http://dx.doi.org/10.3184/0308234053431031.

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The reaction of (E)-(2-oxo-1,2-dihydroindol-3-ylidene)acetic acid esters (1) with methyl ethyl ketone in the presence of morpholine as a catalyst gave 4-oxo-2-(2-oxo-2,3-dihydro-1H-indole-3-yl)hexanoic acid esters, a diastereomeric mixture of two isomers (2A and 2B). Using aluminium oxide as a catalyst for the above reaction led to the formation of 4-oxo-3-methyl-2-(2-oxo-2,3-dihydro–1H-indole-3-yl)-pentanoic acid esters as a mixture of three isomers 3A, 3B and 3C, which upon methylation with methyl iodide in acetone and in the presence of anhydrous potassium carbonate yield the corresponding methylated products. The structural assignments of the new compounds are based on their chemical and spectroscopic properties. The stereochemical structures of 5aA, 5bB and 5aC are identified by X-ray analysis.
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22

Eisch, John J. "Emergence of electrophilic alumination as the counterpart of established nucleophilic lithiation: an academic sojourn in organometallics with William Kaska as fellow traveler." Dalton Transactions 44, no. 15 (2015): 6671–79. http://dx.doi.org/10.1039/c4dt01036a.

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23

Mercer, Frank W. "Synthesis and Properties of Aromatic Poly(Ether Ketone Pyridazine)s." High Performance Polymers 5, no. 4 (August 1993): 275–83. http://dx.doi.org/10.1088/0954-0083/5/4/002.

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A general method for the preparation of pyridazine-containing aromatic poly(ether ketone)s has been developed. Polymerization is based on a ketone-activated nucleophilic halo displacement in pyridazine containing bis(4-fluorobenzoyl) moieties by phenoxides. 3,6-Bis(4-fluorobenzoyl-4'-phenoxy-4"-phenoxy)pyridazine was prepared by reaction of 4-fluorobenzoyl chloride with 3,6-bis(4-phenoxyphenoxy)pyrfdazine in dichloromethane in the presence of aluminum chloride. Reaction 3,6-bis(4-fluorobenzoyl-(4-phenoxy-4phenoxy)pyridazine with diphenols in an aprotic solvent in the presence of potassium carbonate gave a series of aromatic poly(ether ketone pyridazine)s. Films of the aromatic poly(ether ketone pyrdazine)s displayed good thermal stability, flexibility, and T. values ranging from 159 to 198 'C. The dielectric constants of the films were characterized as a function of relative humidity (RH).
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24

Wang, Kang-Kyun, Bong-Jin Kim, Si-Hwan Ko, Dong Hoon Choi, and Yong-Rok Kim. "Fabrication of Photofunctional Nanoporous Membrane and Its Photoinactivation Effect of Vesicular Stomatitis Virus." Journal of Nanomaterials 2012 (2012): 1–7. http://dx.doi.org/10.1155/2012/454507.

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Fabrication and photophysical study of photofunctional nanoporous alumina membrane (PNAM) were performed, and its application of photodynamic antimicrobial chemotherapy (PACT) was investigated. Nanoporous alumina membrane (NAM) was fabricated by two-step aluminium anodic oxidation process. Surface of the fabricated NAM was modified with organo-silane agent to induce covalent bonding between NAM and a photosensitizer (PtCP: [5,10,15-triphenyl-20-(4-methoxycarbonylphenyl)-porphyrin] platinum). PtCP was covalently bonded to the surface of the modified NAM by nucleophilic acyl substitution reaction process. The morphology and the photophysical properties of the fabricated PNAM were confirmed with field emission scanning electron microscope (FE-SEM), steady-state spectroscopies, and nanosecond laser-induced time-resolved spectroscopy. For the efficacy study of PNAM in PACT, an enveloped animal virus, vesicular stomatitis virus (VSV), was utilized as a target organism. Antiviral effect of the PNAM-PACT was measured by the extent of suppression of plaque-forming units (PFU) after the light irradiation. In the cultures inoculated with PACT-treated VSV, the suppression of PFU was prominent, which demonstrates that PNAM is a potential bio clean-up tool.
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25

Zhang, Zaihui, T. L. Thomas Hui, and Chris Orvig. "One-pot synthesis of N-substituted-3-hydroxy-4-pyridinone chelate complexes of aluminum, gallium, and indium." Canadian Journal of Chemistry 67, no. 11 (November 1, 1989): 1708–10. http://dx.doi.org/10.1139/v89-263.

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A series of tris(3-hydroxy-2-methyl-4-pyridinonato)metal(III) and tris(3-hydroxy-6-hydroxymethyl-4-pyridinonato)metal(III) complexes have been prepared in water by one-pot synthesis directly from maltol and kojic acid, respectively, and the metal ion (M = Al, Ga, In) with an appropriate amine. The pyridinones have substituents at the ring nitrogen atom (CH3, C2H5). The tris(3-hydroxy-4-pyronato)metal(III) complexes are formed insitu and these undergo nucleophilic attack by the primary amine; the appropriate tris(3-hydroxy-4-pyridinonato)metal(III) complexes are obtained. This method bypasses the sequential syntheses of ligand and metal complex, and has improved the yields of the tris(ligand)metal complexes, in particular by making them much more easily accessible. The electronic effects of binding the pyrone to the metal ions and of the substituents on the pyrone ring on the reactivity are discussed. Keywords: 3-hydroxy-4 pyridinone complexes, group 13 metal ions, one-pot synthesis.
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26

Shimizu, Makoto, Chiaki Yamauchi, and Toshiki Ogawa. "Double Nucleophilic Addition of Azide and Tetramethallyltin to α,β-Unsaturated Aldimines Promoted by Aluminum Chloride." Chemistry Letters 33, no. 5 (May 2004): 606–7. http://dx.doi.org/10.1246/cl.2004.606.

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27

Power, Michael B., Andrew R. Barron, Simon G. Bott, and Jerry L. Atwood. ".pi.-Face selectivity of coordinated ketones to nucleophilic additions: the importance of aluminum-oxygen .pi.-bonding." Journal of the American Chemical Society 112, no. 9 (April 1990): 3446–51. http://dx.doi.org/10.1021/ja00165a031.

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28

Tian, Guocai, Huanhuan Du, and Hongmei Zhang. "First Principle Analysis on Pyridine Amide Derivatives’ Adsorption Behavior on the Pt (111) Surface." Crystals 11, no. 2 (January 24, 2021): 98. http://dx.doi.org/10.3390/cryst11020098.

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The reactivity and adsorption behavior of three pyridine amide additives (Nicotinamide, Pyridine-2-formamide and Pyridine-4-formamide) on the Pt (111) surface was studied by First principle methods. The quantum chemical calculations of molecular reactivity show that the frontier orbitals of the three additives are distributed around the pyridine ring, oxygen atom of carbonyl and nitrogen atom of amino, and the nucleophilic and electrophilic active centers are located on the nitrogen atoms of pyridine ring, oxygen atom of carbonyl and nitrogen atom of amino. All three molecules were adsorbed with the chemical adsorption on the Pt (111) surface, and the order of adsorption was Nicotinamide > Pyridine-2-formamide > Pyridine-4-formamide. The C and N atoms of three derivatives forms C-Pt and N-Pt bonds with the Pt atoms of the Pt (111) surface, which makes derivatives stably adsorb on the Pt surface and form a protective film. The protective film inhibits the diffusion of atoms to the surface of the growth center, so as to inhibit the formation of dendrite and obtain a smooth aluminum deposition layer.
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29

BARRIUSO, E., J. M. PORTAL, and F. ANDREUX. "CINÉTIQUE ET MÉCANISME DE L'HYDROLYSE ACIDE DE LA MATIÈRE ORGANIQUE D'UN SOL HUMIFÈRE DE MONTAGNE." Canadian Journal of Soil Science 67, no. 3 (August 1, 1987): 647–58. http://dx.doi.org/10.4141/cjss87-061.

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From the surface horizon of an organic-rich mountain soil, humic and fulvic acids, and organo-mineral compounds including clay and hydroxy-metal colloids, were separated and purified. Each of these fractions was hydrolyzed in 3.0 M HCl under reflux, then the reaction parameters related to the solubilization of carbon and nitrogen and to the kinetics of hydrolysis were calculated. Acid hydrolysis was interpreted as the result of two successive steps: first a rapid electrophilic attack of heteroatomic C-O and C-N bonds by protons, then a slow nucleophilic hydration of the protonated bonds. Electron delocalization in these bonds, which increased with the polycondensation degree of organic compounds, and with their adsoprtion on mineral surfaces, resulted in an increase in their stability to hydrolysis. Fulvic acids were found to be the less stable material, and lead to predominantly anionic hydrolysis products. Clay-sized humin was the most stable material and yielded mainly cationic hydrolysates. The stability to hydrolysis and the humification degree of organic matter in the fractions generally coincided, and decreased in the following order: fine clay-sized humin > alkali dispersible organo-mineral colloids > > humic acids > hydroxy-ferric organic colloids > hydroxy-aluminium organic colloids = fulvic acids. Key words: Organo-mineral complex, humic substances, acid hydrolysis, carbon, nitrogen
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30

Maruoka, Keiji, Masahiro Ito, and Hisashi Yamamoto. "Unprecedented nucleophilic addition of organolithiums to aromatic aldehydes and ketones by complexation with aluminum tris(2,6-diphenylphenoxide)." Journal of the American Chemical Society 117, no. 35 (September 1995): 9091–92. http://dx.doi.org/10.1021/ja00140a036.

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31

Morse, Graham E., and Timothy P. Bender. "Aluminum Chloride Activation of Chloro-Boronsubphthalocyanine: a Rapid and Flexible Method for Axial Functionalization with an Expanded Set of Nucleophiles." Inorganic Chemistry 51, no. 12 (May 29, 2012): 6460–67. http://dx.doi.org/10.1021/ic2016935.

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32

Baer, Hans H., and Miroslawa Mekarska-Falicki. "Stereochemical dependence of the mechanism of deoxygenation, with lithium triethylborohydride, in 4,6-O-benzylidenehexopyranoside p-toluenesulfonates." Canadian Journal of Chemistry 63, no. 11 (November 1, 1985): 3043–52. http://dx.doi.org/10.1139/v85-505.

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Lithium triethylborohydride was shown to react with methyl 4,6-O-benzylidene-α-D-hexopyranoside 2- and 3-tosylates, and 2,3-ditosylates, in the manno, allo, and altro configurational series both by O—S fission (O-desulfonylation) and by C—O fission (C-desulfonyloxylation), to produce carbinol and deoxy functions, respectively. The results were compared with those previously obtained with the corresponding gluco and galacto isomers, and the degree of facility of the cleavage reactions was seen to depend on the position of the sulfonic ester groups and the overall configuration of the molecules. The mechanism of reductive desulfonyloxylation also depended on configuration and was demonstrated to involve intermediary epoxide formation or displacement by internal hydride shift as the principal paths; competing elimination and direct nucleophilic displacement were found to occur in the allo series, whereas reduction accompanied by ring contraction has thus far been encountered only in the conformationally less constrained, cis-fused acetal system of the galacto series. Like the borohydride reagent, lithium aluminum hydride was found to react (though much more slowly) with the altro 2,3-ditosylate by the epoxide-mediated mechanism, although the latter hydride is known to desulfonyloxylate the α-D-gluco-isomer by a different, intramolecular reduction mechanism.
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33

Shimizu, Makoto, Toshiki Ogawa, and Takafumi Nishi. "Double nucleophilic addition reaction to α,β-unsaturated aldimines promoted by aluminum chloride and a limited amount of water." Tetrahedron Letters 42, no. 32 (August 2001): 5463–66. http://dx.doi.org/10.1016/s0040-4039(01)01021-8.

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34

Shimizu, Makoto, Makiko Kamiya, and Iwao Hachiya. "Double Nucleophilic Addition of Trimethylsilyl Cyanide to α,β-Unsaturated Aldimines Promoted by Aluminum Chloride: Preparation of 2-Aminopentanedinitrile." Chemistry Letters 34, no. 10 (October 2005): 1456–57. http://dx.doi.org/10.1246/cl.2005.1456.

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35

MARUOKA, K., M. ITO, and H. YAMAMOTO. "ChemInform Abstract: Unprecedented Nucleophilic Addition of Organolithiums to Aromatic Aldehydes and Ketones by Complexation with Aluminum Tris(2,6- diphenylphenoxide)." ChemInform 26, no. 52 (August 13, 2010): no. http://dx.doi.org/10.1002/chin.199552052.

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36

Sugimoto, Hiroshi, Takuzo Aida, and Shohei Inoue. "Lewis acid-promoted living anionic polymerization of alkyl methacrylates initiated with aluminum porphyrins. Importance of steric balance between a nucleophile and a Lewis acid." Macromolecules 27, no. 13 (June 1994): 3672–74. http://dx.doi.org/10.1021/ma00091a033.

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37

Dmowski, Wojciech. "Nucleophilic reactions of fluoroolefins. VI. Reactions of 1-phenylpentafluoropropene with lithium aluminium hydride. Regio- and stereoselective substitution of vinylic fluorines by hydrogen." Journal of Fluorine Chemistry 29, no. 3 (September 1985): 273–86. http://dx.doi.org/10.1016/s0022-1139(00)82327-1.

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38

Shimizu, Makoto, Makiko Kamiya, and Iwao Hachiya. "Double Nucleophilic Addition of Ketene Silyl (Thio)acetals and Trimethylsilyl Cyanide to α,β-Unsaturated Aldimines Promoted by Aluminum Chloride." Chemistry Letters 32, no. 7 (July 2003): 606–7. http://dx.doi.org/10.1246/cl.2003.606.

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39

Takeda, Norihiko, Erika Futaki, Yukiko Kobori, Masafumi Ueda, and Okiko Miyata. "Nucleophilic Arylation of N ,O -Ketene Acetals with Triaryl Aluminum Reagents: Access to α-Aryl Amides through an Umpolung Process." Angewandte Chemie International Edition 56, no. 51 (November 27, 2017): 16342–46. http://dx.doi.org/10.1002/anie.201708665.

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40

Takeda, Norihiko, Erika Futaki, Yukiko Kobori, Masafumi Ueda, and Okiko Miyata. "Nucleophilic Arylation of N ,O -Ketene Acetals with Triaryl Aluminum Reagents: Access to α-Aryl Amides through an Umpolung Process." Angewandte Chemie 129, no. 51 (November 27, 2017): 16560–64. http://dx.doi.org/10.1002/ange.201708665.

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41

Kuroki, Masakatsu, Tsuyoshi Watanabe, Takuzo Aida, and Shohei Inoue. "Steric separation of nucleophile and Lewis acid providing dramatically accelerated reaction. High-speed polymerization of methyl methacrylate with enolate-aluminum porphyrin/sterically crowded organoaluminum systems." Journal of the American Chemical Society 113, no. 15 (July 1991): 5903–4. http://dx.doi.org/10.1021/ja00015a077.

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42

Ramsden, Nigel G., George W. J. Fleet, and Sung Keon Namgoong. "Interception of an iminium ion equivalent by intramolecular nucleophilic attack by a silyl ether during lithium aluminium hydride reduction of a tertiary lactam." Journal of the Chemical Society, Perkin Transactions 2, no. 12 (1991): 1991. http://dx.doi.org/10.1039/p29910001991.

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43

Olah, George A., Imre Bucsi, Christian Lambert, Robert Aniszfeld, Nirupam J. Trivedi, Dilip K. Sensharma, and G. K. Surya Prakash. "Chlorination and bromination of fullerenes. Nucleophilic methoxylation of polychlorofullerenes and their aluminum trichloride catalyzed Friedel-Crafts reaction with aromatics to polyarylfullerenes." Journal of the American Chemical Society 113, no. 24 (November 1991): 9385–87. http://dx.doi.org/10.1021/ja00024a063.

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44

Park, Seung Un, Sung Kee Chung, and Martin Newcomb. "Evidence supporting two-electron nucleophilic displacement in reactions of unhindered alkyl bromides and iodides with boron and aluminum hydride reducing agents." Journal of Organic Chemistry 52, no. 15 (July 1987): 3275–78. http://dx.doi.org/10.1021/jo00391a017.

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45

Shimizu, Makoto, Toshiki Ogawa, and Takafumi Nishi. "ChemInform Abstract: Double Nucleophilic Addition Reaction to α,β-Unsaturated Aldimines Promoted by Aluminum Chloride and a Limited Amount of Water." ChemInform 32, no. 43 (May 24, 2010): no. http://dx.doi.org/10.1002/chin.200143075.

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46

Reheim, Mohamed A. M. A., Ibrahim S. A. Hafiz, and Hend S. E. A. Rady. "Utility of Diketone in Heterocyclic Synthesis: Synthesis of New Substituted Pyrimidines and Fused Pyrimidine of Potential Biosignificant Interest." Current Organic Synthesis 15, no. 8 (December 17, 2018): 1171–81. http://dx.doi.org/10.2174/1570179415666180918161101.

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Aim and Objective: In this study, a new series of iminopyrimidine derivatives were synthesized from the reaction of the key intermediate 2-imino-6-phenyl-2,3-dihydropyrimidin-4(5H)-one 4 with a variety of electrophilic and nucleophilic reagents under a variety of mild conditions. The structures of the newly synthesized compounds were characterized on the basis of their elemental analysis and spectroscopic data. The antimicrobial activity of this series was evaluated in vitro and they showed either weak or moderate activities. Materials and Methods: All melting points were measured using Akofler Block instrument and are uncorrected. IR spectra (KBr) were recorded on FTIR 5300 spectrometer (υ, cm-1). The 1H NMR spectra were recorded on a Varian Gemini spectrometer. The 1H NMR spectra were run at 400 MHz and 13C NMR spectra were run at 100 MHz in DMSO-d6 as a solvent. The chemical shifts are expressed in parts per million (ppm) by using tetramethylsilane (TMS) as an internal reference. 1000 EX mass spectrometer at 70 eV. The purity of synthesized compounds was checked by Thin Layer Chromatography (TLC) (aluminum sheets) using n-hexane, ethyl acetate (7:3, V/V) eluent. Elemental analysis was carried out by the Microanalytical Research Center, Faculty of Science, and Microanalytical Unit, Faculty of Pharmacy, Cairo University, Egypt. Conclusion: In conclusion, compounds 4, 5 and 12 were used as efficient precursors for the synthesis of new heterocycles including 2-imino-2,3-dihydropyrimidine moiety with expected biological activities.
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47

Nayl, AbdElAziz A., Ashraf A. Aly, Wael A. A. Arafa, Ismail M. Ahmed, Ahmed I. Abd-Elhamid, Esmail M. El-Fakharany, Mohamed A. Abdelgawad, Hendawy N. Tawfeek, and Stefan Bräse. "Azides in the Synthesis of Various Heterocycles." Molecules 27, no. 12 (June 9, 2022): 3716. http://dx.doi.org/10.3390/molecules27123716.

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In this review, we focus on some interesting and recent examples of various applications of organic azides such as their intermolecular or intramolecular, under thermal, catalyzed, or noncatalyzed reaction conditions. The aforementioned reactions in the aim to prepare basic five-, six-, organometallic heterocyclic-membered systems and/or their fused analogs. This review article also provides a report on the developed methods describing the synthesis of various heterocycles from organic azides, especially those reported in recent papers (till 2020). At the outset, this review groups the synthetic methods of organic azides into different categories. Secondly, the review deals with the functionality of the azido group in chemical reactions. This is followed by a major section on the following: (1) the synthetic tools of various heterocycles from the corresponding organic azides by one-pot domino reaction; (2) the utility of the chosen catalysts in the chemoselectivity favoring C−H and C-N bonds; (3) one-pot procedures (i.e., Ugi four-component reaction); (4) nucleophilic addition, such as Aza-Michael addition; (5) cycloaddition reactions, such as [3+2] cycloaddition; (6) mixed addition/cyclization/oxygen; and (7) insertion reaction of C-H amination. The review also includes the synthetic procedures of fused heterocycles, such as quinazoline derivatives and organometal heterocycles (i.e., phosphorus-, boron- and aluminum-containing heterocycles). Due to many references that have dealt with the reactions of azides in heterocyclic synthesis (currently more than 32,000), we selected according to generality and timeliness. This is considered a recent review that focuses on selected interesting examples of various heterocycles from the mechanistic aspects of organic azides.
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48

Hirabe, Tomoatsu, Masato Takagi, Kiyoshige Muraoka, Masatomo Nojima, and Shigekazu Kusabayashi. "Lithium aluminum hydride reduction of 1-aryl-3-halopropenes, 1-aryl-3-halobutenes, and (9-anthryl)arylmethyl halides. Nucleophilic substitution vs. single electron transfer." Journal of Organic Chemistry 50, no. 11 (May 1985): 1797–802. http://dx.doi.org/10.1021/jo00211a002.

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49

RAMSDEN, N. G., G. W. J. FLEET, and S. K. NAMGOONG. "ChemInform Abstract: Interception of an Iminium Ion Equivalent by Intramolecular Nucleophilic Attack by a Silyl Ether During Lithium Aluminum Hydride Reduction of a Tertiary Lactam." ChemInform 23, no. 13 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199213302.

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50

Viñals, F., X. Testar, M. Palacín, and A. Zorzano. "Inhibitory effect of fluoride on insulin receptor autophosphorylation and tyrosine kinase activity." Biochemical Journal 291, no. 2 (April 15, 1993): 615–22. http://dx.doi.org/10.1042/bj2910615.

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Fluoride is a nucleophilic reagent which has been reported to inhibit a variety of different enzymes such as esterases, asymmetrical hydrolases and phosphatases. In this report, we demonstrate that fluoride inhibits tyrosine kinase activity of insulin receptors partially purified from rat skeletal muscle and human placenta. Fluoride inhibited in a similar dose-dependent manner both beta-subunit autophosphorylation and tyrosine kinase activity for exogenous substrates. This inhibitory effect of fluoride was not due to the formation of complexes with aluminum and took place in the absence of modifications of insulin-binding properties of the insulin receptor. Fluoride did not complete with the binding site for ATP or Mn2+. Fluoride also inhibited the autophosphorylation and tyrosine kinase activity of receptors for insulin-like growth factor I from human placenta. Addition of fluoride to the pre-phosphorylated insulin receptor produced a slow (time range of minutes) inhibition of receptor kinase activity. Furthermore, fluoride inhibited tyrosine kinase activity in the absence of changes in the phosphorylation of prephosphorylated insulin receptors, and the sensitivity to fluoride was similar to the sensitivity of the unphosphorylated insulin receptor. The effect of fluoride-on tyrosine kinase activity was markedly decreased when insulin receptors were preincubated with the copolymer of glutamate/tyrosine. Prior exposure of receptors to free tyrosine or phosphotyrosine also prevented the inhibitory effect of fluoride. However, the protective effect of tyrosine or phosphotyrosine was maximal at low concentrations, suggesting the interaction of these compounds with the receptor itself rather than with fluoride. These data suggest: (i) that fluoride interacts directly and slowly with the insulin receptor, which causes inhibition of its phosphotransferase activity; (ii) that the binding site of fluoride is not structurally modified by receptor phosphorylation; and (iii) based on the fact that fluoride inhibits phosphotransferase activity in the absence of alterations in the binding of ATP, Mn2+ or insulin, we speculate that fluoride binding might affect the transfer of phosphate from ATP to the tyrosine residues of the beta-subunit of the insulin receptor and to the tyrosine residues of exogenous substrates.
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