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Journal articles on the topic 'Mechanism of aromatic nucleophilic'

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Published: 5 June 2025

Last updated: 1 August 2025

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1

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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2

Lu, Xiaosong, and John Warkentin. "Mechanism of ipso aromatic substitution by reaction of aryloxy(methoxy)carbenes and diaryloxycarbenes with DMAD." Canadian Journal of Chemistry 79, no. 4 (2001): 364–69. http://dx.doi.org/10.1139/v01-029.

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Some aryloxy(methoxy)carbenes and diaryloxycarbenes attack dimethyl acetylenedicarboxylate (DMAD) with aryl group transfer to an alkyne carbon of DMAD. In this study diaryloxycarbenes with different aryl groups that could be transferred competitively, were generated in the presence of DMAD to probe for the mechanism of that ipso aromatic substitution. It was found that a para electron-withdrawing substituent, relative to an electron-donating substituent, facilitated migration of an aryl group. Mechanisms in accord with these findings involve initial nucleophilic attack by the carbene at an alk

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3

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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4

Onuoha, Goddy N., Ikenna Onyido, and Jack Hirst. "Mechanism of aromatic nucleophilic substitution in aprotic solvents." Journal of the Chemical Society, Perkin Transactions 2, no. 6 (1988): 971. http://dx.doi.org/10.1039/p29880000971.

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5

Sharma, Nishant, Rupayan Biswas, and Upakarasamy Lourderaj. "Dynamics of a gas-phase SNAr reaction: non-concerted mechanism despite the Meisenheimer complex being a transition state." Physical Chemistry Chemical Physics 22, no. 45 (2020): 26562–67. http://dx.doi.org/10.1039/d0cp05567k.

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6

Marquet, Jorge, Francisco Casado, Maria Cervera, et al. "Reductively activated 'polar' nucleophilic aromatic substitution. A new mechanism in aromatic chemistry?" Pure and Applied Chemistry 67, no. 5 (1995): 703–10. http://dx.doi.org/10.1351/pac199567050703.

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7

Newmark, H. L. "Plant phenolics as inhibitors of mutational and precarcinogenic events." Canadian Journal of Physiology and Pharmacology 65, no. 3 (1987): 461–66. http://dx.doi.org/10.1139/y87-079.

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Initiation of chemical carcinogenesis involves the intracellular formation of a highly reactive electrophile that can attack many chemical nucleophiles in the cell, including DNA, a process that seems to be a central mechanism of initiation. Competing chemical nucleophiles in the cell, such as endogenous glutathione, can act as protecting or blocking agents against the attack on DNA. There are chemical substances in our food supply that may act as anticarcinogens or antimutagens by blocking or trapping ultimate carcinogen electrophiles in a nucleophilic chemical reaction, to form innocuous pro

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8

Chupakhin, Oleg N., and Valery N. Charushin. "Nucleophilic C–H functionalization of arenes: a new logic of organic synthesis." Pure and Applied Chemistry 89, no. 8 (2017): 1195–208. http://dx.doi.org/10.1515/pac-2017-0108.

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AbstractDirect metal-free C–H functionalization of arenes with nucleophiles is a new chapter in the chemistry of aromatics. Comprehensive studies on nucleophilic substitution of hydrogen in arenes (the SNH reactions), including mechanisms, intermediates, mathematic and electrochemical modeling, kinetics, electron-transfer, etc. have shown that this is not the hydride ion, but C–H proton is departed, and this process is facilitated by the presence of an appropriate oxidant or an auxiliary group. The SNH reactions, as a part of the general C–H functionalization concept, change the logic of organ

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9

Gazitúa, Marcela, Ricardo A. Tapia, Renato Contreras, and Paola R. Campodónico. "Mechanistic pathways of aromatic nucleophilic substitution in conventional solvents and ionic liquids." New J. Chem. 38, no. 6 (2014): 2611–18. http://dx.doi.org/10.1039/c4nj00130c.

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10

Tanaka, Kiyoshi, Makoto Deguchi, and Satoru Iwata. "Ab initio Study of Nucleophilic Aromatic Substitution of Polyfluorobenzene." Journal of Chemical Research 23, no. 9 (1999): 528–29. http://dx.doi.org/10.1177/174751989902300905.

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Calculations at ab initio levels of theory of the nucleophilic aromatic substitution of pentafluoronitrobenzene with amines demonstrate an addition–elimination mechanism (SNAr), with the rate-determining step at the second transition state involving C–F bond breaking, and support the ortho-selectivity of the reactions based on the stability of the second transition states.

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11

Casella, Girolamo, Maurizio Casarin, Vadim Kukushkin, and Maxim Kuznetsov. "Reaction between Indazole and Pd-Bound Isocyanides—A Theoretical Mechanistic Study." Molecules 23, no. 11 (2018): 2942. http://dx.doi.org/10.3390/molecules23112942.

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The mechanism of the addition of indazole (Ind)—a bifunctional aromatic N,NH-nucleophile—to cyclohexyl isocyanide coordinated to the palladium(II) center in the model complex cis-[PdCl2(CNMe)(CNCy)] (1) to give the corresponding aminocarbene ligand was investigated in detail by theoretical (DFT) methods. The most plausible mechanism of this reaction is that of the associative type involving nucleophilic attack of Ind by its unprotonated N atom at the isocyanide carbon atom followed by the stepwise proton transfer from the nucleophile molecule to the isocyanide N atom via deprotonation/protonat

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12

Bao, Xingping, Guangyu Xu, Jinzhong Yao, and Hongwei Zhou. "Aromatic Pummerer reaction for the remote para- or ortho-benzyl nucleophilic functionalization." Organic Chemistry Frontiers 5, no. 6 (2018): 1019–21. http://dx.doi.org/10.1039/c7qo00970d.

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The classic Pummerer reaction involves an α-substituted sulfide via an elimination/addition of a thionium ion. In this paper, we reported a remote para- or ortho-benzyl nucleophilic functionalization using an aromatic Pummerer process. A plausible mechanism involving a quinone thionium intermediate was proposed to explain this reaction.

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13

Langhals, Heinz, and Maximilian Rauscher. "NIR Absorption of Perylene Dyes and Fluorescence with Large Stokes’ Shift by Simple Deprotonation." Zeitschrift für Naturforschung B 68, no. 5-6 (2013): 683–86. http://dx.doi.org/10.5560/znb.2013-3090.

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A brightly red fluorescent 1-hydroxyperylene bisimide was prepared by a nucleophilic aromatic displacement reaction. The deprotonation of the hydroxy group shifts the absorption and the strong fluorescence into the NIR. A selected medium promotes an ESPT mechanism and induces a large Stokes’ shift of nearly 200 nm in the NIR

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14

Cunningham, Ian D. "Kinetics and mechanism of nucleophilic addition of hydroxide to aromatic isocyanides." Journal of the Chemical Society, Perkin Transactions 2, no. 8 (1988): 1485. http://dx.doi.org/10.1039/p29880001485.

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15

Adolfo Cuesta, Sebastián, Tania Cordova‐Sintjago, and José Ramón Mora. "Sulfonylation of Five‐Membered Aromatic Heterocycles Compounds through Nucleophilic Aromatic Substitution: Concerted or Stepwise Mechanism?" ChemistrySelect 5, no. 15 (2020): 4515–24. http://dx.doi.org/10.1002/slct.202000656.

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16

Masuya, Yoshihiro, Yuki Kawashima, Takuya Kodama, Naoto Chatani, and Mamoru Tobisu. "Thiolate-Initiated Synthesis of Dibenzothiophenes from 2,2′-Bis(methylthio)-1,1′-Biaryl Derivatives through Cleavage of Two Carbon–Sulfur Bonds." Synlett 30, no. 17 (2019): 1995–99. http://dx.doi.org/10.1055/s-0037-1611974.

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A catalytic reaction involving the cleavage of two carbon–sulfur bonds in 2,2′-bis(methylthio)-1,1′-biaryl derivatives is reported. This reaction does not require a transition-metal catalyst and is promoted by a thiolate anion. Notably, based on DFT calculations, the product-forming cyclization step is shown to proceed through a concerted nucleophilic aromatic substitution (CSNAr) mechanism.

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17

Mazal, Ctibor, та Jaroslav Jonas. "Nucleophilic Vinylic Substitution on α-Tosyloxymethylene Lactones". Collection of Czechoslovak Chemical Communications 58, № 7 (1993): 1607–23. http://dx.doi.org/10.1135/cccc19931607.

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Sodium salt of 3-hydroxymethylenetetrahydro-2H-pyran-2-one (V), obtained by Claisen condensation of δ-valerolactone with ethyl formate, was converted into its sulfonates and carboxylates IV, VII - X, which were obtained either as pure E-isomers or as mixtures of E- and Z-isomers; the mixtures were chromatographically separated. Substitution reaction of α-tosyloxymethylene lactones II, III and IV with aromatic thiols, azide anion, secondary amines and sodium enolates XI, XII and V was studied. The stereochemical outcome of this substitution is discussed from the viewpoint of mechanism of nucleo

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18

Holm, Andrew Thomas, Sanatan Nayak, and Philip Wai Hong Chan. "Gold-Catalysed Oxidative Cycloisomerisation of 1,6-Diyne Acetates to 1-Naphthyl Ketones." Australian Journal of Chemistry 72, no. 11 (2019): 881. http://dx.doi.org/10.1071/ch19330.

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A synthetic method to prepare 1-naphthyl ketones from gold(i)-catalysed oxidative cycloisomerisation of 1,6-diyne acetates is described. The proposed mechanism involves cyclopropenation–cycloreversion of the 1,6-diyne motif initiated by a 1,2-acyloxy migration. This is followed by nucleophilic attack of the ensuing gold carbenoid species by a molecule of water and autoxidation to give the aromatic product.

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19

CRAMPTON, M. R. "ChemInform Abstract: Nucleophilic Aromatic Substitution (Organic Reaction Mechanisms)." ChemInform 22, no. 45 (2010): no. http://dx.doi.org/10.1002/chin.199145325.

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20

CRAMPTON, M. R. "ChemInform Abstract: Nucleophilic Aromatic Substitution (Organic Reaction Mechanisms)." ChemInform 25, no. 13 (2010): no. http://dx.doi.org/10.1002/chin.199413288.

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21

Morgantini, PY, P. Fluekiger, and J. Weber. "Computer modeling of the activation processes of the aromatic nucleophilic substitution mechanism." Journal de Chimie Physique 89 (1992): 1723–28. http://dx.doi.org/10.1051/jcp/1992891723.

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22

Nudelman, Norma S. "The ?dimer mechanism? in aromatic nucleophilic substitution by amines in aprotic solvents." Journal of Physical Organic Chemistry 2, no. 1 (1989): 1–14. http://dx.doi.org/10.1002/poc.610020102.

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23

Lu, Ka, Xiao Feng, Chao-Xian Yan, et al. "Chiral phosphoric acid catalyzed asymmetric arylation of indoles via nucleophilic aromatic substitution: mechanisms and origin of enantioselectivity." Catalysis Science & Technology 10, no. 7 (2020): 2277–92. http://dx.doi.org/10.1039/d0cy00008f.

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Asymmetric arylation of indoles via nucleophilic aromatic substitution can be effectively achieved using chiral phosphoric acid as catalyst, where the mechanisms and origin of enantioselectivity were explored theoretically.

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24

Couture, Christiane, and Anthony James Paine. "Mechanisms and models for homogeneous copper mediated ligand exchange reactions of the type: CuNu + ArX → ArNu + CuX." Canadian Journal of Chemistry 63, no. 1 (1985): 111–20. http://dx.doi.org/10.1139/v85-019.

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The title reactions are an important class of copper mediated nucleophilic aromatic substitution processes, which constitute a useful tool in the molecular design and synthesis of small molecules. We report the results of extensive investigation of these processes, primarily focussing on cyanodeiodination (ArI + CuCN → CuI + ArCN). Among the interesting features of these processes are: (a) an unusual rate equation involving autocatalysis by CuI product; (b) retardation by both excess nucleophile (as KCN) and excess leaving group (as KI), which compete with ArX to complex with CuNu; (c) only cu

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25

Shemehen, R., O. Khilya, and Yu Volovenko. "REACTION OF 2-HETARYL-2-(DIHYDROFURAN-2(3H)-ILIDEN)ACETONITRILES WITH AROMATIC AMINES." Bulletin of Taras Shevchenko National University of Kyiv. Chemistry, no. 1 (57) (2020): 47–51. http://dx.doi.org/10.17721/1728-2209.2020.1(57).12.

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This article reports on the reaction of 2-hetaryl-2-(furanyl-2-ylidene)acetonitriles with aromatic amines as N-nucleophiles. 2-Hetaryl-2-(furanyl-2-ylidene)acetonitriles represent versatile building blocks in syntheses of ω-(N-aryl)alkyl substituted heterocycles due to the presence of 1,3-bielectrophilic acrylonitrile fragment functionalized with unsaturated heterocyclic ring and nucleophilic azaheterocyclic moiety. The carbonyl group masked within the N-arylpyrrolidinylidene fragment which undergoes a ring opening through the reaction with nucleophiles. So, a method for the synthesis of 2-het

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26

Ibrahim, Mahmoud F., Hanaa A. Abdel-Reheem, and Ezzat A. Hamed. "NUCLEOPHILIC SUBSTITUTION REACTIONS OF 2, 4-DINITTROPHENYL ACETATE WITH HYDRAZINE AND METHANOL SOLVENT EFFECT." EPH - International Journal of Applied Science 6, no. 1 (2020): 23–26. http://dx.doi.org/10.53555/eijas.v6i1.106.

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The generally accepted mechanism for nucleophilic aromatic substitution (the snare mechanism) is an addition-elimination mechanism and involves the formation of a Meisenheimer type of intermediate. The hydrazinolysis of 2,4-dinitrophenyl acetate in methanol proceeds exclusively through acyl-oxygen scission by a concerted mechanism. The process depends on the basicity of the leaving group and its steric hindrance as well as the possible intramolecular hydrogen bond in the transition state. The reactions of 2,4Dinittrophenyl Acetate with hydrazine obeyed pseudo-first-order rate constants (kobs).

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27

Kuznetsova, Anastasiya, Philipp Klein, and Till Opatz. "Halogenated 2,1,3-benzoxadiazoles as Potential Fluorescent Warheads for Covalent Protease Inhibitors." Proceedings 9, no. 1 (2018): 54. http://dx.doi.org/10.3390/ecsoc-22-05670.

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Recently there has been a growing interest in covalent protease inhibitors in both industry and academia, caused by their longer residence times, their higher potency and their high ligand efficiency. Covalently reactive moieties which interact with activated amino acid residues such as serine or cysteine in enzymes like proteases or esterases mostly act through nucleophilic addition, substitution or ring opening. In contrast, nucleophilic aromatic substitution (SNAr) is rarely employed. In our previous work, we prepared and investigated electrophilic “warheads”, which contain aromatic, hetero

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28

Osipov, Dmitry V., Kirill S. Korzhenko та Vitaly A. Osyanin. "Three-Component Condensation of β-Ketonitriles, 4-Fluorobenzaldehyde, and Secondary Cyclic Amines". Reactions 3, № 4 (2022): 625–33. http://dx.doi.org/10.3390/reactions3040042.

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A new three-component condensation of β-ketonitriles, 4-fluorobenzaldehyde, and secondary cyclic amines was developed. A possible reaction mechanism has been proposed including Knoevenagel condensation followed by aromatic nucleophilic substitution. It was found that in the case of 3-oxopropanenitrile bearing the 6-amino-1,3-dimethyluracil moiety, the reaction is not accompanied by fluorine substitution in the Knoevenagel adduct, and the Michael addition of a secondary amine occurs followed by oxidation.

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29

Domingo, Luis R., Mar Ríos-Gutiérrez, Eduardo Chamorro, and Patricia Pérez. "Are one-step aromatic nucleophilic substitutions of non-activated benzenes concerted processes?" Organic & Biomolecular Chemistry 17, no. 35 (2019): 8185–93. http://dx.doi.org/10.1039/c9ob01589b.

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Analysis of the mechanism of one-step S<sub>N</sub>Ar reactions of non-activated benzenes shows the presence of structures similar to those of Meisenheimer intermediates, thus accounting for the non-concerted nature of these reactions.

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30

Kumykov, Ruslan M., and Arsen K. Vologirov. "NEW AROMATIC DINITRODERIVATIVES OF CHLORAL AS MONOMER FOR SYNTHESYS OF POLYESTER AND POLYHETERO-ARYLENE." IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENIY KHIMIYA KHIMICHESKAYA TEKHNOLOGIYA 61, no. 2 (2018): 4. http://dx.doi.org/10.6060/tcct.20186102.5613.

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The synthesis of aromatic dinitroderivatives of chloral effectively used in production of soluble, heat and fire resistant polyester and polyhetero arylenes using in the reaction of aromatic nucleophilic replacement was studied. The groups of new aromatic dinitroderivatives containing chloral as central groups between the phenyl nuclei: dichlorethelyne, carbonyl, acetylene and methylene groups were considered. The synthesis conditions were improved for polyester polyesterketones, polyesteretherketones, poliftalimides and polynaphtalamids without substantially affecting the thermal and solid ch

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31

Acevedo, Orlando, and William L. Jorgensen. "Solvent Effects and Mechanism for a Nucleophilic Aromatic Substitution from QM/MM Simulations." Organic Letters 6, no. 17 (2004): 2881–84. http://dx.doi.org/10.1021/ol049121k.

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32

Kang, Yan-Fei, Li-Ya Niu, and Qing-Zheng Yang. "Fluorescent probes for detection of biothiols based on “aromatic nucleophilic substitution-rearrangement” mechanism." Chinese Chemical Letters 30, no. 10 (2019): 1791–98. http://dx.doi.org/10.1016/j.cclet.2019.08.013.

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33

Jacobsson, Mårten, Jonas Oxgaard, Carl-Olof Abrahamsson, Per-Ola Norrby, William A Goddard, and Ulf Ellervik. "Acid-Catalyzed Nucleophilic Aromatic Substitution: Experimental and Theoretical Exploration of a Multistep Mechanism." Chemistry - A European Journal 14, no. 13 (2008): 3954–60. http://dx.doi.org/10.1002/chem.200701590.

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34

Arvanites, Anthony C., and Donald W. Boerth. "Modeling of the mechanism of nucleophilic aromatic substitution of fungicide chlorothalonil by glutathione." Journal of Molecular Modeling 7, no. 7 (2001): 245–56. http://dx.doi.org/10.1007/s008940100032.

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35

Kochetova, Ludmila B., and Tatiana P. Kustova. "Kinetics and mechanism of acyl transfer reactions. Part 15. Quantumchemicalsimulation of mechanisms of reactions of N-ethylaniline sulfonation." Butlerov Communications 57, no. 2 (2019): 19–27. http://dx.doi.org/10.37952/roi-jbc-01/19-57-2-19.

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The RHF/6-31G(d) quantum chemical simulation of the mechanism of the interaction of the secondary fatty aromatic amine N-ethylaniline with benzenesulfonyl chloride under conditions of non-specific water solvation, using the continuum model of the solvent, as well as of sulfonylation reactions of N-ethylaniline solvation complexes containing one water molecule, modeled specific solvation of N-ethylaniline with water, and one molecule of water and one of dioxane, which simulate the solvation of the amine with aqueous dioxane. Three-dimensional potential energy surface of these processes is calcu

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36

Krylov, Evgeny N., and Lyudmila V. Virzum. "Molecular electrostatic potential of the reaction center as a descriptor of the reactivity of arylsulfonyl halides." Butlerov Communications 64, no. 11 (2020): 33–41. http://dx.doi.org/10.37952/roi-jbc-01/20-64-11-33.

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To study the reactivity of arylsulfonyl halides, the molecular electrostatic potential (MEP) was considered for the first time as a descriptor. The reaction of hydrolysis of aromatic sulfonyl halides in the medium of mixed acetone-water solvents (according to the literature data of rate constants) was used as a model. The calculation of the structural parameters of the molecules of substituted arylsulfonyl halides was carried out using the ADF2014 software package at the level of the DFT/M06/6-311+G* (PCM) theory. It was found that the magnitude of the MEP on the sulfonyl sulfur atom is very s

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37

Sanecki, Przemyslaw, and Edward Rokaszewski. "Kinetics of hydrolysis of aromatic mono- and disulfonyl chlorides." Canadian Journal of Chemistry 65, no. 9 (1987): 2263–67. http://dx.doi.org/10.1139/v87-377.

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A continuous polarographic method of recording instantaneous concentrations of —SO2Cl groups in an aqueous acetic acid system containing CH3CO2Na has been elaborated. Ten model monosulfonyl chlorides underwent hydrolysis according to pseudo-first order kinetics (20% H2O, 80% v.v. CH3CO2H, 0.5 mol × dm−3 CH3CO2Na). Plots of hydrolysis for seven disulfonyl dichlorides with different number of —CH3 groups have been determined. Pseudo-first order rate constants for two consecutive reactions of hydrolysis (k1 and k2) have been computed and the influence of —SO2Cl and [Formula: see text] groups on t

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38

Chavan, Arun B., Sanjeev M. Reddy, and G. Krishna Chaitanya. "Elucidating Reaction Mechanism of Gefitinib- An Anticancer Drug by Computational Technique." Oriental Journal Of Chemistry 40, no. 3 (2024): 835–40. http://dx.doi.org/10.13005/ojc/400327.

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The present investigation centres on the application of quantum chemistry to clarify the innovative synthetic pathway for Gefitinib derived from methyl 2-isocyano-4,5-dimethoxybenzoate. This pathway encompasses various chemical reactions such as cyclization, halogenation, regioselective demethylation, Williamson's ether synthesis, and nucleophilic aromatic substitution. The reaction necessitates the presence of four intermediate species and yields a total of 11 transition states [TS]. The energies of each reactant, intermediate, and product were determined through the utilisation of density fu

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39

Artamkina, G. A., A. Yu Mil'chenko, I. P. Beletskaya, and O. A. Reutov. "Effect of nature of the nucleophile on the mechanism of nucleophilic aromatic substitution reactions involving fluorenyl and trimethylstannyl anions." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 37, no. 12 (1988): 2550–56. http://dx.doi.org/10.1007/bf00952638.

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40

Nakagaki, Ryoichi, Mitsuo Hiramatsu, Kiyoshi Mutai, and Saburo Nagakura. "Photo-Smiles Rearrangement (IV) Electron-Transfer Mechanism of an Intra-Molecular Aromatic Nucleophilic Substitution." Molecular Crystals and Liquid Crystals 126, no. 1 (1985): 69–75. http://dx.doi.org/10.1080/15421408508084155.

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41

Lubis, Siti Masitah, Muhamad Fadhly Hariadi, Nilna Amalia, et al. "One-Pot Synthesis and Antioxidant Activity of 4-Phenoxyquinoline Derivative from Clove Leaf Oil." Materials Science Forum 1068 (August 19, 2022): 161–66. http://dx.doi.org/10.4028/p-3q70s0.

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Synthesis and antioxidant assay of 4-phenoxyquinoline derivative namely, (E)-7-chloro-4-(2-methoxy-4-(prop-1-en-1-yl)phenoxy)quinoline, from clove leaf oil have been conducted. This compound can be prepared from eugenol (isolated from clove leaf oil) in either two-step or one-pot synthesis. In two-step synthesis, eugenol was subjected to base-catalyzed-isomerization to give isoeugenol, which in turn underwent aromatic nucleophilic aromatic nucleophilic substitution with 4,7-dichloroquinoline to generate (E)-7-chloro-4-(2-methoxy-4-(prop-1-en-1-yl)phenoxy)quinoline in 57% total yields. By combi

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42

RajanBabu, T. V., G. S. Reddy, and Tadamichi Fukunaga. "Nucleophilic addition of silyl enol ethers to aromatic nitro compounds: scope and mechanism of reaction." Journal of the American Chemical Society 107, no. 19 (1985): 5473–83. http://dx.doi.org/10.1021/ja00305a024.

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43

Döring, Thomas, Romesh C. Boruah, and Wolfgang Pfleiderer. "Synthesis of 7-Acyl-2,4-disubstituted Pteridines by Radical Nucleophilic Substitution and Displacement Reactions." Pteridines 15, no. 4 (2004): 129–48. http://dx.doi.org/10.1515/pteridines.2004.15.4.129.

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Abstract 2,4-Disubstituted pteridine derivatives (1-3) react with acyl radicals very selectively in position 7 by a nucleophilic Substitution mechanism (4-10). Oxidation of the 2-methylthio group proceeds with m-chloroperbenzoic acid in good yields to the corresponding 7-acyl-2-methylsulfonyl-4-aminopteridines (11-16). The methylsulfonyl group can easily been displaced by nucleophiles such as aliphatic amines (27, 29, 32-42, 45), cyclic amines (56-61), aromatic amines (30, 31) and amino acids (43-54). Oxygen nucleophiles lead to 7-acyl-isopterin derivatives (62-66). The acyl side-chain is also

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44

Dvorak, Trevor, Haley Hernandez-Sandoval, Sunayn Cheku, et al. "Development of a Rapid-Response Fluorescent Probe for H2S: Mechanism Elucidation and Biological Applications." Biosensors 15, no. 3 (2025): 174. https://doi.org/10.3390/bios15030174.

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Hydrogen sulfide (H2S) is an important signaling molecule involved in various physiological and pathological processes, making its accurate detection in biological systems highly desirable. In this study, two fluorescent probes (M1 and M2) based on 1,8-naphthalimide were developed for H2S detection via a nucleophilic aromatic substitution. M1 demonstrated high sensitivity and selectivity for H2S in aqueous media, with a detection limit of 0.64 µM and a strong linear fluorescence response in the range of 0–22 µM of NaHS. The reaction kinetics revealed a rapid response, with a reaction rate cons

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Akinyele, Elizabeth T., Ikenna Onyido, and J. Hirst. "Mechanisms of aromatic nucleophilic substitution reactions in ethyl acetate and tetrahydrofuran." Journal of Physical Organic Chemistry 3, no. 1 (1990): 41–47. http://dx.doi.org/10.1002/poc.610030109.

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Berven, Leise A., David Dolphin, and Stephen G. Withers. "The base-catalysed anomerization of dinitrophenyl glycosides: evidence for a novel reaction mechanism." Canadian Journal of Chemistry 68, no. 10 (1990): 1859–66. http://dx.doi.org/10.1139/v90-288.

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The mechanism of base-catalysed anomerization of per-O-acetylated 2,4-dinitrophenyl-β-D-glucopyranoside in dimethylsulfoxide has been investigated using a variety of techniques. A mechanism involving proton abstraction at C-1 was eliminated by the absence of proton exchange at that center and the measurement of a secondary deuterium kinetic isotope effect for the 1-deuterio substrate. A mechanism involving phenolate departure and recombination is rendered unlikely on the basis of remote substituent effects on the reaction rate and by the absence of any exchange of the phenyl moiety with added

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Palleros, Daniel R., and N. Sbarbati Nudelman. "The effect of a hydrogen bond acceptor catalyst on the dimer mechanism in aromatic nucleophilic substitution." Journal of the Chemical Society, Perkin Transactions 2, no. 4 (1985): 479. http://dx.doi.org/10.1039/p29850000479.

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Enoch, S. J., T. W. Schultz, and M. T. D. Cronin. "The definition of the applicability domain relevant to skin sensitization for the aromatic nucleophilic substitution mechanism." SAR and QSAR in Environmental Research 23, no. 7-8 (2012): 649–63. http://dx.doi.org/10.1080/1062936x.2012.679691.

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Al-Lohedan, Hamad A., and Anthony J. Kirby. "Solvent effects on aromatic nucleophilic substitution by the ANRORC mechanism. Hydrolysis of 2-chloro-3,5-dinitropyridine." Journal of the Chemical Society, Perkin Transactions 2, no. 7 (1995): 1283. http://dx.doi.org/10.1039/p29950001283.

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Wubbels, Gene G., та Kandra M. Johnson. "New Nitronate σ Complexes and the Mechanism of Nucleophilic Aromatic Photosubstitution Para to a Nitro Group". Organic Letters 8, № 7 (2006): 1451–54. http://dx.doi.org/10.1021/ol0602497.

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