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Journal articles on the topic 'Nucleofuge effect'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Um, Ik-Hwan, Ji-Youn Lee, Sun-Young Bae та Erwin Buncel. "Effect of modification of the electrophilic center on the α effect". Canadian Journal of Chemistry 83, № 9 (2005): 1365–71. http://dx.doi.org/10.1139/v05-157.

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We report on a nucleophilic study of esters R-C(=X)-Y-Ar in which the electrophilic center has been modified by replacing O by S in the leaving group or carbonyl center: 4-nitrophenyl acetate (1), S-4-nitrophenyl thioacetate (2), 4-nitrophenyl benzoate (3), and O-4-nitrophenyl thionobenzoate (4). The studies include O and S nucleophiles as well as α nucleophiles in H2O at 25.0 ± 0.1 °C. The sulfur nucleophile (4-chlorothiophenoxide, 4-ClPhS) exhibits significant enhanced reactivity for the reactions with thiol and thione esters 2 and 4 compared with their oxygen analogues 1 and 3. On the co

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2

Humeres, Eduardo, Valdir Soldi, Marilene Klug, Mauricéa Nunes, Célia MS Oliveira, and Patrick J. Barrie. "Hydrolysis and aminolysis of alkyl xanthate esters and cellulose analogues." Canadian Journal of Chemistry 77, no. 5-6 (1999): 1050–56. http://dx.doi.org/10.1139/v99-107.

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The hydrolysis and aminolysis of a series of S-substituted O-alkylxanthate esters was studied in 20% v/v aqueous methanol at 35°C. The pH-rate profiles of the hydrolyses showed water and hydroxide-ion-catalyzed reactions. The reaction of 2,4-dinitrophenyl cellulose xanthate (CelXDNP) and p-nitrobenzyl cellulose xanthate (CelXNB) with polyalanine and lysozyme produced a covalent bond between the polypeptide and the cellulose matrix, as shown by solid-state 13C NMR. However, the nature of the bonding could not be identified. The reaction of nucleophiles (H2O, OH-, RNH2) and xanthic esters was co

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3

Glancy, John H., Daniel M. Lee, Emily O. Read, and Ian H. Williams. "Computational simulation of mechanism and isotope effects on acetal heterolysis as a model for glycoside hydrolysis." Pure and Applied Chemistry 92, no. 1 (2020): 75–84. http://dx.doi.org/10.1515/pac-2019-0221.

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AbstractDFT calculations for the equilibrium isotope effect for deuterium substitution at the anomeric centre Cα in 2-(p-nitrophenoxy)tetrahydropyran with continuum solvation show significant variation in the range of relative permittivity 2 ≤ ε ≤ 10. One-dimensional scans of potential energy (with implicit solvation by water) or of free energy (from QM/MM potentials of mean force with explicit aqueous solvation with a hybrid AM1/OPLS method) for heterolysis of the bond between Cα and the nucleofuge do not show a transition state. A two-dimensional free-energy surface that considers also the d

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4

Gurudas, Bhattacharjee, Kumar Singh Ashok, Singh Rupam, and Gairola Priti. "Nucleofuge effect : the kinetic and mechanistic studies of the reactions of some O-aryloximes and phenyl naphthyl ether with n-butylamine in acetonitrile." Journal of Indian Chemical Society Vol. 80, Feb 2003 (2003): 95–99. https://doi.org/10.5281/zenodo.5836528.

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Department of Chemistry, Indian Institute of Technology - Roorkee, Roorkee-24 7 667, India <em>E-mail :</em> wordgfcy@iitr.ernet.in <em>Manuscript received 2 September 2002, accepted 25 November 2002</em> The aminolysis reactions of <em>O</em>-(2',4'-dinitrophenyl)-2-naphthol (DNPN), <em>O</em>-(2',4'-dinitrophenyl)indanoneoxime (DNPIO), and <em>O</em>-(2,4-dinitrophenyl)propanoneoxime (DNPPO) have been carried out with <em>n</em>-butylamine in acetonitrile at 35 ± 0.1º. The coloured product obtained in each case was <em>N</em>-(2,4-dinitrophenyl)butylamine, in addi

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5

Cao, Weiguo, Ihsan Erden, Richard H. Grow, et al. "Article." Canadian Journal of Chemistry 77, no. 5-6 (1999): 1009–34. http://dx.doi.org/10.1139/v99-061.

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Equilibrium and rate constants have been determined for the acid-catalyzed heterolysis of two alcohols, 9-xanthydrol and p-anisyldiphenylmethanol, and two sulfides, (9-xanthyl) methyl sulfide and (7-tropyl) methyl sulfide. These data together with literature information are compared with rate constants for acid-catalyzed C-C heterolysis of several (9-xanthyl) compounds, (7-tropyl) compounds, a set of 3-arylcyclobutanones, and two 2-arylnitrocyclopropanes, all of which fragment to carbocations plus a carbon-centered nucleofuge. The fragmentation mechanisms are shown to be A1 or A1(ion pair) exc

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6

Denegri, Bernard, Mirela Matić, and Olga Kronja. "Impact of Electronic Effects on the Nucleofugality of Leaving Groups." Synthesis 49, no. 15 (2017): 3422–32. http://dx.doi.org/10.1055/s-0036-1590792.

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A short review of the development of nucleofugality and electrofugality scales based on solvolysis rates of benzhydryl derivatives is presented. Accordingly, the rate of the heterolytic step in the SN1 displacement reaction and the leaving group ability (nucleofugality) in a given solvent are related with the special linear free-energy relationship (LFER) equation: log k = s f (N f + E f). The impact of electronic effects in the leaving group (nucleofuge) on the overall SN1 reactivity of the substrate is given. The importance of inductivity, resonance, polarity and field effects in the leaving

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7

Blanco Trillo, Roberto, Jörg M. Neudörfl, and Bernd Goldfuss. "An unusually stable chlorophosphite: What makes BIFOP–Cl so robust against hydrolysis?" Beilstein Journal of Organic Chemistry 11 (March 4, 2015): 313–22. http://dx.doi.org/10.3762/bjoc.11.36.

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Two chlorophosphites, the biphenyl-based BIFOP–Cl and the diphenyl ether-based O–BIFOP–Cl, exhibit striking differences regarding their reaction with water. While BIFOP–Cl is nearly completely unreactive, its oxo-derivative O–BIFOP–Cl reacts instantly with water, yielding a tricyclic hydrocarbon unit after rearrangement. The analysis of the crystal structure of O–BIFOP–Cl and BIFOP–Cl revealed that the large steric demand of encapsulating fenchane units renders the phosphorus atom nearly inaccessible by nucleophilic reagents, but only for BIFOP–Cl. In addition to the steric effect, a hypervale

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8

Kang, Ji-Sun, and Ik-Hwan Um. "Kinetics and Reaction Mechanism for Aminolysis of Benzyl 4-Pyridyl Carbonate in H2O: Effect of Modification of Nucleofuge from 2-Pyridyloxide to 4-Pyridyloxide on Reactivity and Reaction Mechanism." Bulletin of the Korean Chemical Society 33, no. 7 (2012): 2269–73. http://dx.doi.org/10.5012/bkcs.2012.33.7.2269.

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9

Dvorko, G. F., I. V. Koshchii, and E. A. Ponomareva. "Kinetics and mechanism of unimolecular heterolysis of cage-like compounds: XIX. Effect of the nucleofuge nature on the activation parameters of heterolysis of 1-halo-1-methylcyclohexanes in cyclohexane. Heterolysis rate ratio in aprotic and protic solvents." Russian Journal of Organic Chemistry 43, no. 1 (2007): 50–55. http://dx.doi.org/10.1134/s1070428007010046.

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10

Doroshkevich, Victor S., Oksana V. Baranova, Aleksandr N. Shendrik, Aleksandr S. Doroshkevich, Olena S. Lygina, and Svitlana B. Lyubchyk. "Study of Extraction Equilibria in the Reaction of Alkaline Hydrolysis of Activated Amino Acid Esters / Badanie Równowag Ekstrakcji W Reakcji Zasadowej Hydrolizy Aktywowanych Estrów Aminokwasów." Chemistry-Didactics-Ecology-Metrology 19, no. 1-2 (2014): 69–77. http://dx.doi.org/10.1515/cdem-2014-0006.

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Abstract Correlation between observed kinetic effects of phase-transfer catalytic reaction of the alkaline hydrolysis of 4-nitrophenyl ester of N-benzyloxycarbonylglycine-4 in the two-phase system chloroform-borate buffer pH = 10 and a content of ionic forms of catalyst was investigated. The phosphonium salts QX (X = Cl¯, Br¯, I¯) shows high catalytic reactivity. Dependence of the reaction kinetics discussed in the framework of the extraction mechanism with a competitive extraction of a nucleophile ОН¯, nucleofuge 4-NO2C6H4O¯ and anion X¯ of the phase-transfer catalyst.

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11

Rappoport, Zvi, and Alain Topol. "Nucleophilic attacks on carbon-carbon double bonds. Part 39. Nucleophile and nucleofuge effects, catalysis and stereochemistry in vinylic substitution of electrophilic nitro olefins." Journal of Organic Chemistry 54, no. 25 (1989): 5967–77. http://dx.doi.org/10.1021/jo00286a033.

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12

Khazaei, Kobra, Juliana H. F. Yeung, Margo M. Moore, and Andrew J. Bennet. "Inhibitory efficiencies for mechanism-based inactivators of sialidases." Canadian Journal of Chemistry 93, no. 11 (2015): 1207–13. http://dx.doi.org/10.1139/cjc-2015-0245.

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Here we describe the measurement of the inactivation rate constants for the mechanism-based inactivator 2,3-difluorosialic acid acting upon the sialidase from Micromonospora viridifaciens. Using double mixing stopped-flow experiments conducted in a 3-(N-morpholino)propanesulfonic acid buffer (100 mmol/L, pH 7.00) at 25 °C, the derived kinetic parameters are kinact/Ki = (3.9 ± 0.8) × 106 (mol/L)–1 s–1 and Ki = 1.7 ± 0.4 μmol/L. We demonstrate that the inhibitory efficiency of the inactivation event is similar to the catalytic efficiency for this sialidase acting upon a typical substrate, 4-meth

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13

Montecinos, Rodrigo, Marcela Gazitúa, and José G. Santos. "The effect of the electrophilic group on the hierarchy of nucleofuges in the aminolysis reactions of thiol- and dithiocarbonates with secondary alicyclic amines: A kinetic and theoretical study." New Journal of Chemistry 43, no. 16 (2019): 6372–79. http://dx.doi.org/10.1039/c9nj00385a.

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Thiol- and dithiocarbonates react with amines, forming tetrahedral intermediates and then different product ratios. Theoretical results show that the product ratio depends on the water microsolvation of the electrophilic group in the anionic intermediate.

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14

Avramovitch, Bianca, Peter Weyerstahl, and Zvi Rappoport. "Nucleophilic attacks on carbon-carbon double bonds. 34. Intramolecular elements effect in competitive expulsion of two halide nucleofuges as a tool for investigating the rapid step of nucleophilic vinylic substitution." Journal of the American Chemical Society 109, no. 22 (1987): 6687–97. http://dx.doi.org/10.1021/ja00256a023.

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15

Dvorko, G. F., I. V. Koshchii, and E. A. Ponomareva. "Kinetics and Mechanism of Monomolecular Heterolysis of Commercial Organohalogen Compounds: XXXVII.1Effect of Nucleofuge and Solvent of the Relative Rates of Heterolysis of 1-Halo-1-methylcyclopentanes and 1-Halo-1-methylcyclohexanes. Correlation Analysis of Solvation Effects." Russian Journal of General Chemistry 73, no. 9 (2003): 1426–33. http://dx.doi.org/10.1023/b:rugc.0000015993.04565.ee.

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16

"Dehalogenation of polychlorinated biphenyls (PCB) by nucleofile reactants at the presence of ionic liquids and under application of microwaves." Issue 1 13, no. 1 (2013): 59–64. http://dx.doi.org/10.30955/gnj.000668.

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Laboratory-scale experiments were performed in order to examine the effect of microwave field on the effectiveness of KPEG method (nucleophilic substitution of the chlorine atoms in a molecule of PCBs by alkaline polyethylene glycol PEG) in the removal of PCBs from highly contaminated mineral oils with the content of indicator congeners (No 28,52,101,53,138 and 180) above 5500 mg kg-1. Results show that the microwave field significantly increases the reaction rate and the method’s effectiveness in the removal of chlorine from the molecules of PCBs. Addition of a s

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17

AVRAMOVITCH, B., P. WEYERSTAHL, and Z. RAPPOPORT. "ChemInform Abstract: Nucleophilic Attacks on Carbon-Carbon Double Bonds. Part 34. Intramolecular Element Effect in Competitive Expulsion of Two Halide Nucleofuges as a Tool for Investigating the Rapid Step of Nucleophilic Vinylic Substitution." ChemInform 19, no. 7 (1988). http://dx.doi.org/10.1002/chin.198807077.

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