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Journal articles on the topic 'Nucleophilic reaction'

Author: Grafiati

Published: 4 June 2021

Last updated: 8 February 2022

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1

Selimović, Enisa, and Tanja Soldatović. "Study on the reactions between dichlorido[2,2′:6′,2″-terpyridine] zinc(II) and biologically relevant nucleophiles in aqueous solution." Progress in Reaction Kinetics and Mechanism 44, no. 2 (2019): 105–13. http://dx.doi.org/10.1177/1468678319825724.

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Substitution reactions of square-pyramidal [ZnCl2(terpy)] complex (terpy = 2,2′:6′,2″-terpyridine) with biologically relevant nucleophiles such as imidazole, glutathione, 1,2,4-triazole, and pyrazine were investigated at pH 7.0 as a function of nucleophile concentration. The reactions were followed under pseudo first-order conditions by UV-Vis spectrophotometry. The substitution reactions comprised two steps of consecutive displacement of chlorido ligands. Different reaction pathways for the first reaction step of nucleophilic substitution were defined. The order of reactivity of the investiga

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2

Tsuji, Yutaka, and John P. Richard. "Swain–Scott relationships for nucleophile addition to ring-substituted phenonium ions." Canadian Journal of Chemistry 93, no. 4 (2015): 428–34. http://dx.doi.org/10.1139/cjc-2014-0337.

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The products of the reactions of 2-(4-methoxyphenyl)ethyl tosylate (MeO-1-OTs) and 2-(4-methyphenyl)ethyl tosylate (Me-1-OTs) with nucleophilic anions were determined for reactions in 50:50 (v/v) trifluoroethanol (TFE) / water at 25 °C. In many cases, the nucleophile selectivity kNu/ks ((mol/L)−1) for reactions of nucleophile and solvent, calculated from the ratio of product yields, depends upon [Nu−]. This demonstrates the existence of competing reaction pathways, which show different selectivities for reactions with nucleophiles. A 13C NMR analysis of the products of the reactions of substra

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3

Purwono, Bambang, and Estiana R. P. Daruningsih. "NUCLEOPHILIC SUBSTITUTION REACTION OF CYANIDE AND METHOXYDE IONS TO QUATERNARY MANNICH BASE FROM VANILLIN." Indonesian Journal of Chemistry 5, no. 3 (2010): 203–6. http://dx.doi.org/10.22146/ijc.21789.

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The nucleophilic substitution reaction to quaternary Mannich base from vanillin has been investigated. Mannich reaction to vanillin was carried out by refluxing mixture of vanillin, formaldehyde and dimethyl amine. Quaternary ammonium halide salt was obtained from reaction of Mannich vanillin base with methyl iodide in THF solvents and yielded 93.28 %. Nucleophilic substituion to the halide salts with cyanide nucleophile produced 4-hidroxy-3-methoxy-5-(cyano)methylbenzaldehyde in 54.39% yield. Reaction with methoxyde ion yielded 4-hydroxy- 3-methoxy-5-(methoxy) -methylbenzaldehyde in 67.80% yi

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4

Purwono, Bambang, and Estiana E. P. Daruningsih. "NUCHLEOPHILIC SUBSTITUTION REACTION OF CYANIDE AND METHOXYDE IONS TO QUATERNARY MANNICH BASE FROM VANILLIN." Indonesian Journal of Chemistry 7, no. 1 (2010): 58–60. http://dx.doi.org/10.22146/ijc.21713.

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The nucleophilic substitution reaction to quaternary Mannich base from vanillin has been investigated. Mannich reaction to vanillin was carried out by refluxing mixture of vanillin, formaldehyde and dimethyl amine. Quaternary ammonium halide salt was obtained from reaction of Mannich vanillin base with methyl iodide in THF solvents and yielded 93.28%. Nucleophilic substituion to the halide salts with cyanide nucleophile produced 4-hidroxy-3-methoxy-5-(cyano)methylbenzaldehyde in 54.39% yield, with methoxyde ion obtained 4-hidroxy- 3-methoxy-5-(methoxy)-methyl-benzaldehide in 67.80% yield. The

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5

Vilotijevic, Ivan, Markus Lange, and You Zi. "Latent (Pro)Nucleophiles in Enantioselective Lewis Base Catalyzed Allylic Substitutions." Synlett 31, no. 13 (2020): 1237–43. http://dx.doi.org/10.1055/s-0040-1707130.

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The use of latent nucleophiles, which are molecules that are not nucleophilic but can be activated to act as a nucleophile at an opportune time during the reaction, expands the scope of Lewis base catalyzed reactions. Here, we provide an overview of the concept and show examples of applications to N- and C-centered nucleophiles in allylic substitutions. N- and C-silyl compounds are superior latent (pro)nucleophiles in Lewis base catalyzed reactions with allylic fluorides in which the formation of the strong Si–F bond serves as the driving force for the reactions. The latent (pro)nucleophiles e

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6

Dust, Julian M., та Erwin Buncel. "Reactions of the super-electrophile, 2-(2′,4′-dinitrophenyl)-4,6-dinitrobenzotriazole 1-oxide, with methoxide and tert-butoxide: basicity and steric hindrance as factors in σ-complex formation versus nucleophilic displacement". Canadian Journal of Chemistry 69, № 6 (1991): 978–86. http://dx.doi.org/10.1139/v91-143.

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The course of the reactions of methoxide and tert-butoxide with 2-(2′,4′-dinitrophenyl)-4,6-dinitrobenzotriazole 1-oxide (4) clearly shows that the C-7 electrophilic site is significantly more reactive than the C-1′ site of the substrate. The reaction pathways of these alkoxides, which differ in basicity (as a measure of nucleophilicity) and steric bulk, were followed by 400 MHz 1H nuclear magnetic resonance spectroscopy. While both alkoxides lead to immediate formation of the respective C-7 anionic σ-adducts, a greater percentage of C-7 adduct formation occurs with methoxide as attacking nucl

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7

Fang, Yao-ren, Zhu-gen Lai, and Kenneth Charles Westaway. "Isotope effects in nucleophilic substitution reactions X. The effect of changing the nucleophilic atom on ion-pairing in an SN2 reaction." Canadian Journal of Chemistry 76, no. 6 (1998): 758–64. http://dx.doi.org/10.1139/v98-056.

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The effect of ion-pairing in an SN2 reaction is very different when the nucleophilic atom is changed from sulfur to oxygen, i.e., changing the nucleophile from thiophenoxide ion to phenoxide ion. When the nucleophile is sodium thiophenoxide, ion-pairing markedly alters the secondary α -deuterium kinetic isotope effect (transition state structure) and the substituent effect found by changing the para substituent on the nucleophile. When the nucleophile is sodium phenoxide, ion-pairing does not significantly affect the secondary α -deuterium or the chlorine leaving group kinetic isotope effects

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8

Zhang, Xiao, Guo-ping Lu, and Chun Cai. "Facile aromatic nucleophilic substitution (SNAr) reactions in ionic liquids: an electrophile–nucleophile dual activation by [Omim]Br for the reaction." Green Chemistry 18, no. 20 (2016): 5580–85. http://dx.doi.org/10.1039/c6gc01742h.

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9

Imada, Yasushi, Yukihiro Arakawa, Shun Ueta, Takuma Okamoto, and Keiji Minagawa. "Nucleophilic Addition to Nitrones Using a Flow Microreactor." Synlett 31, no. 09 (2020): 866–70. http://dx.doi.org/10.1055/s-0039-1691601.

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Nucleophilic addition reactions of soft carbon nucleophiles to nitrones in a flow microreactor are reported for the first time. Under microflow conditions at 30 to 0 °C, a range of nitrones can be efficiently transformed into the corresponding oxyiminium ions by reaction with either acyl halides or trialkylsilyl triflates. These can subsequently undergo the addition of nucleophiles including allyltributylstannane, ketene methyl tert-butyldimethylsilyl acetal, and N-silyl ketene imines to afford the corresponding adducts in high yields; such reactions at a similar temperature under batch condit

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10

Zhang, Xiao, Guo-ping Lu, and Chun Cai. "Correction: Facile aromatic nucleophilic substitution (SNAr) reactions in ionic liquids: an electrophile–nucleophile dual activation by [Omim]Br for the reaction." Green Chemistry 18, no. 22 (2016): 6143. http://dx.doi.org/10.1039/c6gc90108e.

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Correction for ‘Facile aromatic nucleophilic substitution (S<sub>N</sub>Ar) reactions in ionic liquids: an electrophile–nucleophile dual activation by [Omim]Br for the reaction’ by Xiao Zhang, et al., Green Chem., 2016, 18, 5580–5585.

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11

Damas, Liliana, Rui M. B. Carrilho, Sandra C. C. Nunes, et al. "A novel Pd-catalysed sequential carbonylation/cyclization approach toward bis- N -heterocycles: rationalization by electronic structure calculations." Royal Society Open Science 5, no. 9 (2018): 181140. http://dx.doi.org/10.1098/rsos.181140.

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An unprecedented palladium-catalysed sequential aminocarbonylation/cyclization synthetic strategy, using carbon monoxide and structurally different aliphatic diamines as N -nucleophiles, gives access, in one pot, to a new family of indole-based N -heterocyclic derivatives (hydropyrazinones, benzodiazepinones and hydroquinoxalines). Optimization of the reaction conditions towards double carbonylation ( P CO = 30 bar, T = 80°C, iodoindole/diamine ratio = 1 : 1.5, toluene as solvent) allowed the target cyclic products, which are formed in situ via intramolecular cyclization of the ketocarboxamide

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12

Liljenberg, Magnus, Tore Brinck, Tobias Rein та Mats Svensson. "Utilizing the σ-complex stability for quantifying reactivity in nucleophilic substitution of aromatic fluorides". Beilstein Journal of Organic Chemistry 9 (23 квітня 2013): 791–99. http://dx.doi.org/10.3762/bjoc.9.90.

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A computational approach using density functional theory to compute the energies of the possible σ-complex reaction intermediates, the “σ-complex approach”, has been shown to be very useful in predicting regioselectivity, in electrophilic as well as nucleophilic aromatic substitution. In this article we give a short overview of the background for these investigations and the general requirements for predictive reactivity models for the pharmaceutical industry. We also present new results regarding the reaction rates and regioselectivities in nucleophilic substitution of fluorinated aromatics.

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13

Nudelman, Norma Sbarbati, Cecilia E. Silvana Alvaro, Monica Savini, Viviana Nicotra, and Jeannette Yankelevich. "Effects of the Nucleophile Structure on the Mechanisms of Reaction of 1-Chloro-2,4-dinitrobenzene with Aromatic Amines in Aprotic Solvents." Collection of Czechoslovak Chemical Communications 64, no. 10 (1999): 1583–93. http://dx.doi.org/10.1135/cccc19991583.

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The kinetics of reactions of 1-chloro-2,4-dinitrobenzene with aniline and several substituted aromatic amines, B, in toluene shows a quadratic dependence of the second-order rate constant, kA, on [B], which is preserved even in the presence of increasing amounts of dimethylaniline, while the reaction with N-methylaniline shows a linear dependence of kA vs [B]. All these results are interpreted by the "dimer nucleophile" mechanism, and confirmed by the effects of a non-nucleophilic hydrogen bond acceptor tertiary amine which show the relevance of the structure of the nucleophile and the role of

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14

Zhang, Xin, Jingyun Ren, Siu Min Tan, Davin Tan, Richmond Lee, and Choon-Hong Tan. "An enantioconvergent halogenophilic nucleophilic substitution (SN2X) reaction." Science 363, no. 6425 (2019): 400–404. http://dx.doi.org/10.1126/science.aau7797.

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Bimolecular nucleophilic substitution (SN2) plays a central role in organic chemistry. In the conventionally accepted mechanism, the nucleophile displaces a carbon-bound leaving group X, often a halogen, by attacking the carbon face opposite the C–X bond. A less common variant, the halogenophilic SN2X reaction, involves initial nucleophilic attack of the X group from the front and as such is less sensitive to backside steric hindrance. Herein, we report an enantioconvergent substitution reaction of activated tertiary bromides by thiocarboxylates or azides that, on the basis of experimental and

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15

Crossley, Maxwell J., Lionel G. King, Simon M. Pyke, and Charles W. Tansey. "Reaction of 5-nitro-octaethylporphyrins with nucleophiles." Journal of Porphyrins and Phthalocyanines 06, no. 11 (2002): 685–94. http://dx.doi.org/10.1142/s1088424602000816.

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An investigation of the reactions of metallo-5-nitro-2,3,7,8,12,13,17,18-octaethylporphyrins with Grignard reagents, benzyl oxide, phenoxide and benzenethiolate nucleophiles shows that, except for benzenethiolate reactions, they are less efficient than related reactions of metallo-2-nitro-5,10,15,20-tetraarylporphyrins. Treatment of free-base and nickel(II) 5-nitro-octaethylporphyrin with the “soft” nucleophile benzenethiolate in DMF affords the corresponding 5-phenylthioporphyrins in 61 and 72% yield, respectively, by ipso-substitution of the nitro group. In contrast, with methylmagnesium iod

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16

Yutilova, Kseniia, Yuliia Bespal’ko, and Elena Shved. "A Computational Study of 2-(chloromethyl)oxirane Ring Opening by Bromide and Acetate Anions Considering Electrophilic Activation with Cations of Alkali Metals." Croatica chemica acta 92, no. 3 (2019): 357–67. http://dx.doi.org/10.5562/cca3505.

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Ring opening of 2-(chloromethyl)oxirane via the nucleophilic substitution with bromide and acetate anions was investigated using density functional theory (DFT) calculations. It was shown that the geometry of the transition states and the activation parameters of the reactions correspond to those of SN2-like mechanism. The nature of localized transition states was analyzed using More O’Ferrall – Jencks plots. The quantum chemical simulations of the potential energy surface for the ring-opening reaction of oxirane by nucleophiles confirmed the theoretical assumptions about the favored path of i

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17

Bruneau, Christian, Jean-Luc Renaud, and Bernard Demerseman. "Ruthenium catalysts for selective nucleophilic allylic substitution." Pure and Applied Chemistry 80, no. 5 (2008): 861–71. http://dx.doi.org/10.1351/pac200880050861.

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Recent developments in the chemistry of η3-allylruthenium(IV) complexes are due to their straightforward synthesis resulting from oxidative addition of allylic substrates to a ruthenium(II) center. Subsequent reaction with a nucleophile is the basis of their involvement in the catalytic allylic substitution reaction. We focus here on ruthenium-catalyzed substitution of allylic substrates by C-, N-, and O-nucleophiles and show that selected ligands make regio- and enantioselective reactions possible.

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18

Ameri, Aliakbar Muhamdi. "Principles of Nucleophilic Substitution." American International Journal of Cancer Studies 1, no. 1 (2019): 11–18. http://dx.doi.org/10.46545/aijcs.v1i1.48.

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The work reported in this theoretical paper deals with types of substitution reaction ( sn1 , sn2 , conditions of both reactions , methods of both reactions , diagram of reactions , energy for reactions, types of reactants , products, rate of reactions , steps of reactions, transition state for reaction) and other reactions.

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19

Keddie, Neil S., Pier Alexandre Champagne, Justine Desroches, Jean-François Paquin, and David O'Hagan. "Stereochemical outcomes of C–F activation reactions of benzyl fluoride." Beilstein Journal of Organic Chemistry 14 (January 9, 2018): 106–13. http://dx.doi.org/10.3762/bjoc.14.6.

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In recent years, the highly polar C–F bond has been utilised in activation chemistry despite its low reactivity to traditional nucleophiles, when compared to other C–X halogen bonds. Paquin’s group has reported extensive studies on the C–F activation of benzylic fluorides for nucleophilic substitutions and Friedel–Crafts reactions, using a range of hydrogen bond donors such as water, triols or hexafluoroisopropanol (HFIP) as the activators. This study examines the stereointegrity of the C–F activation reaction through the use of an enantiopure isotopomer of benzyl fluoride to identify whether

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20

Ge, Wen-Zheng, Bao-Ming Wu, and Wei-Yuan Huang. "Nucleophilic substitution reaction in polyfluoroaromatics: I. Reactions with secondary amine nucleophiles." Acta Chimica Sinica 3, no. 4 (1985): 349–55. http://dx.doi.org/10.1002/cjoc.19850030410.

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21

Oh, Young-Ho, Hyoju Choi, Chanho Park, Dong Wook Kim, and Sungyul Lee. "Harnessing Ionic Interactions and Hydrogen Bonding for Nucleophilic Fluorination." Molecules 25, no. 3 (2020): 721. http://dx.doi.org/10.3390/molecules25030721.

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We review recent works for nucleophilic fluorination of organic compounds in which the Coulombic interactions between ionic species and/or hydrogen bonding affect the outcome of the reaction. SN2 fluorination of aliphatic compounds promoted by ionic liquids is first discussed, focusing on the mechanistic features for reaction using alkali metal fluorides. The influence of the interplay of ionic liquid cation, anion, nucleophile and counter-cation is treated in detail. The role of ionic liquid as bifunctional (both electrophilic and nucleophilic) activator is envisaged. We also review the SNAr

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22

Giraudeau, Alain, та Lana El Kahef. "β-Substitution de la méso-tétraphénylporphyrine de zinc par voie électrochimique". Canadian Journal of Chemistry 69, № 7 (1991): 1161–65. http://dx.doi.org/10.1139/v91-173.

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The electrochemical oxidation of the zinc tetraphenylporphyrin complex in a mixed acetonitrile–dichloroethane solution in the presence of nucleophiles (Py, 3-Pic, [Formula: see text], SCN−) leads to the formation of the corresponding monosubstituted metalloporphyrin. For each of these nucleophiles the substitution occurs at a pyrrole carbon atom (β-substitution). The electrochemical conditions of these substitutions are discussed and an overall reaction is proposed. Key words: porphyrins, electrochemical reactions, nucleophilic substitution.

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23

Arcadi, Antonio, Giancarlo Fabrizi, Andrea Fochetti, et al. "Palladium-catalyzed Tsuji–Trost-type reaction of benzofuran-2-ylmethyl acetates with nucleophiles." RSC Advances 11, no. 2 (2021): 909–17. http://dx.doi.org/10.1039/d0ra09601f.

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24

Eom, Ga-eul, and Seokhee Kim. "Identification of Nucleophilic Probes for Protease-Mediated Transpeptidation." Molecules 23, no. 9 (2018): 2109. http://dx.doi.org/10.3390/molecules23092109.

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Proteases have evolved to mediate the hydrolysis of peptide bonds but may perform transpeptidation in the presence of a proper nucleophilic molecule that can effectively compete with water to react with the acyl-enzyme intermediate. There have been several examples of protease-mediated transpeptidation, but they are generally inefficient, and little effort has been made to systematically control the transpeptidation activity of other proteases with good nucleophiles. Here, we developed an on-bead screening approach to find a probe that functions efficiently as a nucleophile in the protease-med

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25

Christoffers, Jens, and David Kieslich. "Cyanide Anions as Nucleophilic Catalysts in Organic Synthesis." Synthesis 53, no. 19 (2021): 3485–96. http://dx.doi.org/10.1055/a-1499-8943.

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AbstractThe nucleophilic addition of a cyanide anion to a carbonyl group is the basis for several cyanide-catalyzed organic reactions, which are summarized in this review. Since cyanide is also a good leaving group, it is an excellent catalyst for transacylation reactions. As an electron-withdrawing group, it also stabilizes a negative charge in its α-position, thus allowing the umpolung of aldehydes to formyl anion equivalents. The two leading examples are the benzoin condensation and the Michael–Stetter reaction furnishing α-hydroxy ketones and 1,4-dicarbonyl compounds, which are both cataly

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26

Kochetova, Ludmila B., Tatyana P. Kustova, and Alyona A. Kruglyakova. "Quantum-chemical study of mechanisms of sulfonation of benzoic and benzenesulfonic acids hydrazides in the gas phase." Butlerov Communications 62, no. 5 (2020): 107–15. http://dx.doi.org/10.37952/roi-jbc-01/20-62-5-107.

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Quantum-chemical simulation of the mechanisms of 3-nitrobenzenesulfonyl chloride interaction with benzhydrazide (RHF/6-31G(d)) and benzenesulfohydrazide (DFT//B3LYP/6 311G(d,p)) in the gas phase was carried out. Three-dimensional potential energy surfaces of these processes are calculated in the coordinates of the angle of attack of the nucleophile and the distance between the reacting molecules. It has been established that in the both cases considered, reactions can proceed in the gas phase along a single route, through a single saddle point corresponding to a single transition state; proces

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27

Birdsall, A. W., C. R. Miner, L. E. Mael, and M. J. Elrod. "Mechanistic study of secondary organic aerosol components formed from nucleophilic addition reactions of methacrylic acid epoxide." Atmospheric Chemistry and Physics Discussions 14, no. 14 (2014): 19917–54. http://dx.doi.org/10.5194/acpd-14-19917-2014.

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Abstract. Recently, methacrylic acid epoxide (MAE) has been proposed as a precursor to an important class of isoprene-derived compounds found in secondary organic aerosol (SOA): 2-methylglyceric acid (2-MG) and a set of oligomers, nitric acid esters and sulfuric acid esters related to 2-MG. However, the specific chemical mechanisms by which MAE could form these compounds have not been previously studied. In order to determine the relevance of these processes to atmospheric aerosol, MAE and 2-MG have been synthesized and a series of bulk solution-phase experiments aimed at studying the reactivi

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28

Birdsall, A. W., C. R. Miner, L. E. Mael, and M. J. Elrod. "Mechanistic study of secondary organic aerosol components formed from nucleophilic addition reactions of methacrylic acid epoxide." Atmospheric Chemistry and Physics 14, no. 23 (2014): 12951–64. http://dx.doi.org/10.5194/acp-14-12951-2014.

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Abstract. Recently, methacrylic acid epoxide (MAE) has been proposed as a precursor to an important class of isoprene-derived compounds found in secondary organic aerosol (SOA): 2-methylglyceric acid (2-MG) and a set of oligomers, nitric acid esters, and sulfuric acid esters related to 2-MG. However, the specific chemical mechanisms by which MAE could form these compounds have not been previously studied with experimental methods. In order to determine the relevance of these processes to atmospheric aerosol, MAE and 2-MG have been synthesized and a series of bulk solution-phase experiments aim

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29

Mahajan, Dinesh, Varun Kumar, Anil Rana, Chhuttan Lal Meena, Nidhi Sharma, and Yashwant Kumar. "Electrophilic Activation of Carboxylic Anhydrides for Nucleophilic Acylation Reactions." Synthesis 50, no. 19 (2018): 3902–10. http://dx.doi.org/10.1055/s-0037-1609564.

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Nucleophilic acylation of symmetrical carboxylic anhydrides has inherited limitation of reaction efficiency along with relatively poor reactivity. Traditionally, one equivalent carboxylic acid is generated during nucleophilic acylation of a symmetrical anhydride, which always limits the yield of final product to 50% or less. This is a major drawback, which discourages the use of anhydrides for laboratory or industrial applications. Electrophilic activation of carboxylic anhydride using methanesulfonyl chloride is found to be an efficient method for nucleophilic acylation, which increases produ

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Bunce, Nigel J., and Karen Labonte Stephenson. "Nucleophilic photosubstitutions of o-methoxynitrobenzenes." Canadian Journal of Chemistry 67, no. 2 (1989): 220–26. http://dx.doi.org/10.1139/v89-037.

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We report a new synthesis of 3-nitroveratrole, based on the directed lithiation of veratrole, and photochemical substitutions of both 3-nitroveratrole and o-nitroanisole with several nucleophiles. Both aromatic substrates undergo photocyanation meta to the nitro group. With hydroxide ion, 3-nitroveratrole reacts meta to the nitro group, but 2-nitroanisole undergoes replacement of either substituent, the proportion of reaction at each site depending upon the OH− concentration. 3-Nitroveratrole undergoes an inefficient reaction with butylamine at each methoxy group; this reaction is apparently s

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31

Abd-El-Aziz, Alaa S., Adam Piórko, Choi Chuck Lee, and Ronald G. Sutherland. "Studies on some selective and competitive substitution reactions of cyclopentadienyliron complexed chloronitrobenzenes with amines as nucleophiles." Canadian Journal of Chemistry 67, no. 10 (1989): 1618–23. http://dx.doi.org/10.1139/v89-247.

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Nucleophilic substitution reactions of the (η6-o-, -m-, or -p-chloronitrobenzene)(η5-cyclopentadienyl)iron cation (2a, 2b, or 2c, respectively) with aniline, n-butylamine, or pyrrolidine as nucleophile were investigated. It was found that only selective displacement of the nitro group occurred for reactions with aniline. For reaction with n-butylamine or pyrrolidine, o-isomer 2a resulted in the selective displacement of only the chloro group, giving rise to the (η6-o-n-butylaminonitrobenzene)(η5-cyclo-pentadienyl)iron cation (5a) or the (η6-o-nitro-N-pyrrolidinylbenzene)(η5-cyclopentadienyl)ir

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32

Deady, LW, and DM Werden. "Nucleophilic-Substitution Reactions in Benzo[C][1,8]Naphthyridines." Australian Journal of Chemistry 39, no. 4 (1986): 667. http://dx.doi.org/10.1071/ch9860667.

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The reactions of 1-chloro-3-methyl-6-(p- methylphenoxy ) benzo [c][1,8] naphthyridine with a variety of nucleophiles are reported. The relative reactivity of the 1- and 6-positions depends on the nucleophile and reaction conditions. Anilines, and alkyl and aryl thioxides react at position 1, alkylamines and alkoxide at position 6, and acidified alcohol at both 1 and 6. Some possible reasons for these positional reactivities are discussed.

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33

Rosenberg, Michal, Štefan Baláž, Ernest Šturdík, and Anton Kuchár. "Reactivity of 2-furylethylenes with nucleophilic groups and its biological significance." Collection of Czechoslovak Chemical Communications 52, no. 2 (1987): 425–30. http://dx.doi.org/10.1135/cccc19870425.

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The paper describes addition-nucleophilic reactions of 1-(5-R1-2-furyl)-2-R2-R3-ethylenes with SH (thioglycolic acid), NH2 (glycine) and OH (phenol) nucleophiles, and with hydroxyl ions in aqueous media. The determined rate constants, of second order (dm3 mol-1 s-1), show that in the physiological conditions the preferential reaction will be that with thiols. The amino acid composition of proteins modified with 1-(5-nitro-2-furyl)-2-nitro-2-methoxycarbonylethylene has revealed that the only group affected was the SH group of cysteine. This finding points out the significance of addition-nucleo

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34

Dust, Julian M., and Richard A. Manderville. "Carbon versus oxygen nucleophilic selectivity in the reaction of the aryloxide ions, 2,6- and 3,5-di-tert-butylphenoxide, with the 2-[(nitro)\dn6 xaryl]-4,6-dinitrobenzotriazole 1-oxide series of super-electrophiles. Stereoelectronic factors on C-7 Meisenheimer complex formation versus C-1' SNAr displacement." Canadian Journal of Chemistry 76, no. 6 (1998): 662–71. http://dx.doi.org/10.1139/v98-028.

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The 2-[(nitro)xaryl]-4,6-dinitrobenzotriazole 1-oxides (1, Pi-DNBT (x = 3); 2, DNP-DNBT (x = 2); 3, NP-DNBT (x = 1)) are electron-deficient nitro-substituted heteroaromatic substrates that possess two sites for nucleophilic attachment: C-7 and C-1'. Generally, attack at the super-electrophilic C-7 site yields spectroscopically observable anionic sigma -bonded adducts, whereas attack at C-1' leads to displacement products in an overall process of nucleophilic aromatic substitution (SNAr). To gain an understanding of the factors affecting C-1' versus C-7 attack by potentially ambident aryloxide

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35

Mathew, George, P. Viswanathan Pillai, and A. P. Kuriakose. "Studies on a New Binary Accelerator System for the Sulfur Vulcanization of Styrene—Butadiene Rubber." Rubber Chemistry and Technology 65, no. 2 (1992): 277–92. http://dx.doi.org/10.5254/1.3538611.

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Abstract The chemical reactions involved when a binary accelerator system is used in rubber vulcanization varies with the systems used. The exact mechanism of these reactions is not fully understood even now. Accelerators in which sulfur is combined as S—S, C—S—C, or S—N are generally inactive at low vulcanization temperatures because of the high thermal stability of their sulfur bonds. But sulfur-containing nucleophiles such as thiourea or its derivatives enable accelerators like TMTD or CBS to operate at lower vulcanization temperature, indicating a nucleophilic reaction mechanism in these v

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36

Cuesta, Sebastián A., F. Javier Torres, Luis Rincón, José Luis Paz, Edgar A. Márquez, and José R. Mora. "Effect of the Nucleophile’s Nature on Chloroacetanilide Herbicides Cleavage Reaction Mechanism. A DFT Study." International Journal of Molecular Sciences 22, no. 13 (2021): 6876. http://dx.doi.org/10.3390/ijms22136876.

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In this study, the degradation mechanism of chloroacetanilide herbicides in the presence of four different nucleophiles, namely: Br−, I−, HS−, and S2O3−2, was theoretically evaluated using the dispersion-corrected hybrid functional wB97XD and the DGDZVP as a basis set. The comparison of computed activation energies with experimental data shows an excellent correlation (R2 = 0.98 for alachlor and 0.97 for propachlor). The results suggest that the best nucleophiles are those where a sulfur atom performs the nucleophilic attack, whereas the other species are less reactive. Furthermore, it was obs

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37

Santos, A. Mafalda, M. Fernanda N. N. Carvalho, Adelino M. Galvão, and Armando J. L. Pombeiro. "Reactivity Trends in the Reaction of Alkynes with 3-Oxo-camphorsulfonylimine." Zeitschrift für Naturforschung B 57, no. 6 (2002): 691–98. http://dx.doi.org/10.1515/znb-2002-0616.

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Abstract The regioselective addition of deprotonated alkynes (phenyl-1-propyne, propargyl ether or tetrahydropyran-protected 3-butyn-1-ol) to the imine group was identified as a competitive process to the nucleophilic addition to the keto group of (1S)-3-oxo-camphorsulfonylimine. The selectivity of the process depends on the characteristics of the nucleophile and the reaction conditions. In the case of propargyl ether it was possible to render the imine addition the main process.The structural characterization of compounds 1, 2, 6 by X-ray diffraction analysis show that the C2 - C3 bond become

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38

Katritzky, Alan R., and Bogumil Brycki. "Kinetics and mechanism of nucleophilic displacements with heterocycles as leaving groups. Part 23. Studies at the borderlines between reactions proceeding (i) via free carbocations, (ii) via rate-determining formation of ion–molecule pairs, and (iii) via rate-determining nucleophilic attack on ion–molecule pairs." Canadian Journal of Chemistry 64, no. 6 (1986): 1161–69. http://dx.doi.org/10.1139/v86-192.

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Evidence is presented to demonstrate that at the borderline between first-order reaction via nucleophilic trapping of intimate ion–molecule pairs and first-order reaction via the formation of free carbocations, both mechanisms proceed independently, without merging. Similarly at the borderline between first-order (rate-determining formation) and second-order (rate-determining nucleophilic attack) reactions of intimate ion–molecule pairs, both reactions again proceed independently.

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39

Kochetova, Ludmila B., Tatyana P. Kustova, and Al’ona A. Kruglyakova. "Quantum-chemical study of mechanisms of benzamide and benzenesulfonamide reactions with 3-nitrobenzenesulfonic acid chloride in the gas phase." Butlerov Communications 63, no. 8 (2020): 86–93. http://dx.doi.org/10.37952/roi-jbc-01/20-63-8-86.

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Quantum-chemical simulation of mechanisms of 3-nitrobenzenesulfonic acid chloride interactions with benzoic and benzenesulfonic acids amides in the gas phase was carried out by calculating the three-dimensional potential energy surfaces of these reactions (DFT//B3LYP/6-311G(d,p) level). It was found that in both of the processes considered, a single route can be realized containing a single saddle point and starting as an axial attack of the nucleophile. Further approach of the reagent molecules proceeds with a decrease in the angle of nucleophilic attack to ≈ 130o in the reaction transition s

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40

Salamov, Ali Kh, Abdulakh K. Mikitaev, Aues A. Beev, Julietti A. Beeva, Mukhamed Kh Ligidov, and Sergey I. Pakhomov. "POLYARYLENEETHERKETONES OBTAINING WITH REACTION OF NUCLEOPHILIC SUBSTITUTION." IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENIY KHIMIYA KHIMICHESKAYA TEKHNOLOGIYA 59, no. 7 (2018): 4. http://dx.doi.org/10.6060/tcct.20165907.5389.

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The article deals with the study of influence of the synthesis conditions on the molecular weight of polyaryleneetherketones (PAEK), received with nucleophilic substitution reaction of activated aryl halide. The synthesis of PAEK with the nucleophilic substitution reaction carried out as partially hydrolyzed homopolycondensation of phenolates and aromatic dihalides containing a carbonyl group in the molecule and derivatives of polycondensation of aromatic bisphenols with activated aromatic dihalides, and aromatic nitro compounds. The nucleophilic substitution of halogen in aryldihalogens proce

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41

Sukhorukov, Alexey, Yana Naumovich, Aleksandr Kokuev та Sema Ioffe. "Synthesis of α-Thiooximes by Addition of Thiols to N,N-Bis(oxy)-enamines: A Comparative Study of S-, N-, and O-Nucleophiles in Michael Reaction with Nitrosoalkene Species". Synlett 29, № 10 (2018): 1334–39. http://dx.doi.org/10.1055/s-0036-1591973.

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Nucleophilic addition of thiols to N,N-bis(oxy)enamines (nitrosoalkene acetals) produce valuable α-thiooximes in a highly efficient manner. The reaction was found to be solvent-dependent, likely because of distinct mechanisms operating in nonpolar and basic solvents (involving either Brønsted acid or Lewis base catalysis). By performing a series of competition experiments, the relative reactivity of S-, N-, and O-nucleophiles in reaction with N,N-bis(oxy)enamines was determined for the first time. Interestingly, the relative nucleophilicity was found to be highly dependent on the solvent, whic

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42

Cheng, Huayu, Xiaofan Zhou, Anjing Hu, et al. "Thioether-functionalized trifluoromethyl-alkynes, 1,3-dienes and allenes: divergent synthesis from reaction of 2-trifluoromethyl-1,3-conjugated enynes with sulfur nucleophiles." RSC Advances 8, no. 59 (2018): 34088–93. http://dx.doi.org/10.1039/c8ra07834c.

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A divergent synthesis of thioether-functionalized trifluoromethyl-alkynes, 1,3-dienes and allenes viaregioselective nucleophilic addition of sulfur nucleophiles to 2-trifluoromethyl-1,3-conjugated enynes was developed.

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43

Zima, Vítězslav, Oldřich Pytela, Jaromír Kaválek, and Miroslav Večeřa. "Reactivity of nucleophiles in dimethyl sulfoxide and its comparison with nucleophilic reactivity in protic medium." Collection of Czechoslovak Chemical Communications 54, no. 10 (1989): 2715–20. http://dx.doi.org/10.1135/cccc19892715.

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Reactions of 2,4-dinitrophenyl acetate and 2,4-dinitrofluorobenzene as model substrates with 12 nucleophiles have been studied in dimethyl sulfoxide. The rate constants obtained have been discussed with regard to the nucleophilic reactivity differences in dimethyl sulfoxide and protic solvents inclusive of the different manifestation of the charge of nucleophiles. The applicability of an earlier-suggested correlation equation to the data obtained has been verified. The reaction medium markedly affects the reactivity of nucleophiles, the effect of charge being substantially greater in aprotic s

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Garçon, Martí, Clare Bakewell, Andrew J. P. White, and Mark R. Crimmin. "Unravelling nucleophilic aromatic substitution pathways with bimetallic nucleophiles." Chemical Communications 55, no. 12 (2019): 1805–8. http://dx.doi.org/10.1039/c8cc09701a.

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Reaction of nucleophiles containing polar (Fe–Mg) and apolar (Mg–Mg) bonds with 2-(pentafluorophenyl)pyridine are calculated to proceed by stepwise and concerted S<sub>N</sub>Ar pathways respectively.

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Mąkosza, Mieczysław. "How Does Nucleophilic Aromatic Substitution in Nitroarenes Really Proceed: General Mechanism." Synthesis 49, no. 15 (2017): 3247–54. http://dx.doi.org/10.1055/s-0036-1588444.

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On the basis of previously published experimental studies and ab initio calculations, a general corrected mechanism of nucleophilic aromatic substitution was formulated. It was shown that conventional nucleophilic substitution of halogens is a slow secondary reaction whereas nucleophilic substitution of hydrogen is the fast primary process. The general mechanism embraces both of these alternative and complementary reactions.

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Jin, Fengyan, Tao Yang, Xian-Rong Song, et al. "TMSBr-Promoted Cascade Cyclization of ortho-Propynol Phenyl Azides for the Synthesis of 4-Bromo Quinolines and Its Applications." Molecules 24, no. 21 (2019): 3999. http://dx.doi.org/10.3390/molecules24213999.

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Difficult-to-access 4-bromo quinolines are constructed directly from easily prepared ortho-propynol phenyl azides using TMSBr as acid-promoter. The cascade transformation performs smoothly to generate desired products in moderate to excellent yields with good functional groups compatibility. Notably, TMSBr not only acted as an acid-promoter to initiate the reaction, and also as a nucleophile. In addition, 4-bromo quinolines as key intermediates could further undergo the coupling reactions or nucleophilic reactions to provide a variety of functionalized compounds with molecular diversity at C4

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Schmidt, Andreas, and Thorsten Mordhorst. "Synthesis of Pyridine-Thioethers via Mono- and Tricationic Pyridinium Salts." Zeitschrift für Naturforschung B 60, no. 6 (2005): 683–87. http://dx.doi.org/10.1515/znb-2005-0613.

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On nucleophilic substitution with S-nucleophiles at room temperature, 1-(4-dimethylamino)- [2,3,5,6-tetrachloropyridin-4-yl]pyridinium chloride (2) yielded tetrachloro-4-sulfanylpyridines and 2,3,5-trichloro-4,6-disulfanylpyridines depending on the reaction conditions. Similarly, the tricationic (3,5-dichloropyridine-2,4,6-triyl)-1,1’,1”-tris[4-(dimethylamino)pyridinium] trichloride 3 was reacted with S-nucleophiles to give the corresponding 3,5-trichloro-2,4,6-trisulfanylpyridines under mild conditions.

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48

Ding, Yan. "A Brief Discussion on Nucleophilic Substitution Reaction on Saturated Carbon Atom." Applied Mechanics and Materials 312 (February 2013): 433–37. http://dx.doi.org/10.4028/www.scientific.net/amm.312.433.

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Nucleophilic substitution reaction is an important reaction of haloalkane. By such a reaction, halogen functional group can turn into various other functional groups. Therefore, it is widely used in organic synthesis and there are many researches on its reaction mechanism. Hydrolysis reaction of bromoalkane is especially a nucleophilic substitution reaction that is studied quite fully. This paper mainly discusses the nucleophilic substitution reaction on saturated carbon atom.

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Havránková, Eva, Jozef Csöllei, and Pavel Pazdera. "New Approach for the One-Pot Synthesis of 1,3,5-Triazine Derivatives: Application of Cu(I) Supported on a Weakly Acidic Cation-Exchanger Resin in a Comparative Study." Molecules 24, no. 19 (2019): 3586. http://dx.doi.org/10.3390/molecules24193586.

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An efficient and simple methodology for Ullmann Cu(I)-catalyzed synthesis of di- and trisubstituted 1,3,5-triazine derivatives from dichlorotriazinyl benzenesulfonamide and corresponding nucleophiles is reported. Cations Cu(I) supported on macroporous and weakly acidic, low-cost industrial resin of polyacrylate type were used as a catalyst. The reaction times and yields were compared with traditional synthetic methods for synthesis of substituted 1,3,5-triazine derivatives via nucleophilic substitution of chlorine atoms in dichlorotriazinyl benzenesulfonamide. It was found that Ullmann-type re

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Bernasconi, Claude F., Rodney J. Ketner, Xin Chen, and Zvi Rappoport. "Detection and kinetic characterization of SNV intermediates. Reactions of thiomethoxybenzylidene Meldrum's acid with thiolate ions, alkoxide ions, OH-, and water in aqueous DMSO." Canadian Journal of Chemistry 77, no. 5-6 (1999): 584–94. http://dx.doi.org/10.1139/v99-009.

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The reaction of thiomethoxybenzylidene Meldrum's acid (5-SMe) with thiolate and alkoxide ion nucleophiles is shown to proceed by the two-step addition-elimination SNV mechanism in which the tetrahedral intermediate accumulates to detectable levels. For the reactions with thiolate ions, rate constants for nucleophilic addition (k1RX), its reverse (k-1RX), and for conversion of the intermediate to products (k2RX) were determined. For the reactions with alkoxide ions, only k1RX and k-1RX could be obtained; the intermediate in these reactions did not yield the expected substitution products, and h

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