Relevant bibliographies by topics / Nucleofuge effect

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Academic literature on the topic 'Nucleofuge effect'

Author: Grafiati
Published: 5 June 2025
Last updated: 1 August 2025

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Journal articles on the topic "Nucleofuge effect"

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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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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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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&#39;,4&#39;-dinitrophenyl)-2-naphthol (DNPN), <em>O</em>-(2&#39;,4&#39;-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 &plusmn; 0.1&ordm;. The coloured product obtained in each case was <em>N</em>-(2,4-dinitrophenyl)butylamine, in addi
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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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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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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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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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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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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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Book chapters on the topic "Nucleofuge effect"

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Okusecyama, Tadashi, and Howard Maskill. "Nucleophilic Substitution Reactions of Haloalkanes and Related Compounds." In Organic Chemistry. Oxford University Press, 2013. http://dx.doi.org/10.1093/hesc/9780199693276.003.0012.

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This chapter covers the substitution reactions of haloalkanes and related compounds under nucleophilic/basic conditions. It emphasizes that haloalkanes and related compounds containing a single bond from a saturated (sp3) carbon to a heteroatom can be represented generically as RY, where R is alkyl and Y is a halogen. The chapter then highlights the two most characteristic reactions of RY (substitution and elimination) under nucleophilic/basic conditions, both involve heterolysis of the bond from the electrophilic carbon to the heteroatom and departure of the nucleofuge. In substitutions, the
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Conference papers on the topic "Nucleofuge effect"

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Peixoto, Bárbara Pereira, José Walkimar de M. Carneiro, and Rodolfo Goetze Fiorot. "Substituição nucleofílica alifática: qual o mecanismo preferencial? Estudo computacional dos efeitos da estrutura do substrato e solvente." In VIII Simpósio de Estrutura Eletrônica e Dinâmica Molecular. Universidade de Brasília, 2020. http://dx.doi.org/10.21826/viiiseedmol2020122.

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Nucleophilic aliphatic substitution reactions constitute important steps in the synthesis of substances with biological activity and industrial appeal, beyond to participating in steps in biosynthetic routes of natural products. Unimolecular (SN1) and bimolecular (SN2) pathways can be understood as limiting cases of a mechanistic continuum. In between them, borderline mechanisms are proposed. The preference for one path over another depends on several factors, such as the structure of the substrate, the nucleophile and the solvent used. This plurality is still a topic of discussion and needs f
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