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Journal articles on the topic 'Nucleophilic substitution reactions'

Author: Grafiati

Published: 4 June 2021

Last updated: 5 February 2022

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1

Kolodiazhnyi, Oleg I. "Stereochemistry of electrophilic and nucleophilic substitutions at phosphorus." Pure and Applied Chemistry 91, no. 1 (2019): 43–57. http://dx.doi.org/10.1515/pac-2018-0807.

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Abstract Nucleophilic and electrophilic substitutions are the most often applied reactions in organophosphorus chemistry. They are closely interrelated, because in a reacting pair always one reagent is an electrophile, and another nucleophile. The reactions of electrophilic and nucleophilic substitutions at the phosphorus center proceed via the formation of a pentacoordinated intermediate. The mechanism of nucleophilic substitution involves the exchange of ligands in the pentacoordinate phosphorane intermediate, leading to the more stable stereomer under the thermodynamic control. Electrophili

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2

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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3

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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4

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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5

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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6

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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7

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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8

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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9

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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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

Dolliver, Debra D., David B. Delatte, Derek B. Linder, James E. Johnson, Diana C. Canesco, and Jeffrey E. Rowe. "Nucleophilic substitution reactions of N-alkoxyimidoyl fluorides by carbon nucleophiles." Canadian Journal of Chemistry 85, no. 11 (2007): 913–22. http://dx.doi.org/10.1139/v07-097.

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Nucleophilic substitutions of N-alkoxybenzoimidoyl fluorides [p-ClArC(F)=NOR; R = CH3, i-Pr] by enolate-type ions have been performed to produce compounds that can exist in two tautomeric forms: the imine form{p-ClArC(Y)=NOR [Y = CH(CN)2, CH(CN)(CO2Et), CH(CO2Et)2]}or the enamine form {p-ClArC(NHOR)=C(R1)(R2) [R1, R2 = CN, CO2Et]}. These compounds display varying ratios of imine–enamine tautomerizm in chloroform: the diester compound exists almost solely in the imine form, the dicyano compound exists solely in the enamine form, and the cyano-ester compound exists in both tautomeric forms. Comp

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12

Kimura, Tsutomu. "Recent Advances in Magnesium Carbenoid Chemistry." Synthesis 49, no. 23 (2017): 5105–19. http://dx.doi.org/10.1055/s-0036-1590894.

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Magnesium carbenoids are a class of organomagnesium species possessing a halo group at the α-position. The reactions of magnesium carbenoids can be classified into the following three categories: nucleophilic reactions resembling Grignard reagents, electrophilic reactions resembling organic halides, and rearrangements resembling carbenes. This short review summarizes recent studies on magnesium carbenoids reported between 2010 and 2016, and milestone studies reported before 2010 according to the classification of the reactions into the aforementioned three categories.1 Introduction2 Structures

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13

Vasilenko, Dmitry A., Sevastian E. Dronov, Dzianis U. Parfiryeu, et al. "5-Nitroisoxazoles in SNAr reactions: access to polysubstituted isoxazole derivatives." Organic & Biomolecular Chemistry 19, no. 29 (2021): 6447–54. http://dx.doi.org/10.1039/d1ob00816a.

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An efficient protocol for the straightforward functionalization of the isoxazole ring via the reactions of aromatic nucleophilic substitution of the nitro group with various nucleophiles has been elaborated.

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14

Guo, Cai-yun, Robert L. Kirchmeier, and Jean'ne M. Shreeve. "Nucleophilic substitution reactions of polyfluoroalkylsulfonamides." Journal of Fluorine Chemistry 52, no. 1 (1991): 29–36. http://dx.doi.org/10.1016/s0022-1139(00)80319-x.

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15

Vogel, Philip, Sarah Figueira, Sivaramakrishnan Muthukrishnan, and James Mack. "Environmentally benign nucleophilic substitution reactions." Tetrahedron Letters 50, no. 1 (2009): 55–56. http://dx.doi.org/10.1016/j.tetlet.2008.10.079.

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16

Rohrbach, Simon, Andrew J. Smith, Jia Hao Pang, et al. "Concerted Nucleophilic Aromatic Substitution Reactions." Angewandte Chemie International Edition 58, no. 46 (2019): 16368–88. http://dx.doi.org/10.1002/anie.201902216.

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17

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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18

Li, Jinhua, Zhengyu Lu, Yuhui Hua, Dafa Chen, and Haiping Xia. "Carbolong chemistry: nucleophilic aromatic substitution of a triflate functionalized iridapentalene." Chemical Communications 57, no. 68 (2021): 8464–67. http://dx.doi.org/10.1039/d1cc03261e.

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19

Cherubim, P., and LW Deady. "Nucleophilic Substitution Reactions in Benzo[C][1,8]naphthyridines. II." Australian Journal of Chemistry 43, no. 8 (1990): 1469. http://dx.doi.org/10.1071/ch9901469.

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3-Chloro-1-methyl-6-(p- methylphenoxy ) benzo [c][1,8] naphthyridine has been prepared, the reactions with various nitrogen, oxygen and sulfur nucleophiles studied, and the results compared with those for the 1- chloro-3-methyl isomer. The 6-position was more reactive for oxygen and nitrogen nucleophiles, so much so that an initially added 6-NHR group was displaced by a second R′NH2 nucleophile at least as readily as was the 3-chloro group. With p- chloro ( thiophenol ), however, the 3-chloro group was preferentially displaced.

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20

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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21

Charushin, V. N., and O. N. Chupakhin. "SNH methodology and new approaches to condensed heterocyclic systems." Pure and Applied Chemistry 76, no. 9 (2004): 1621–31. http://dx.doi.org/10.1351/pac200476091621.

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The review surveys the reactions of electron-deficient azaaromatic compounds with mono- and bifunctional nucleophilies in which a nucleophilic attack at the unsubstituted CH carbon of an aromatic ring is one of the key steps. Use of the SNH methodology for the synthesis of fused heterocyclic systems by means of nucleophilic addition –addition AN–AN, addition –substitution of hydrogen AN–SNH, tandem substitution of hydrogen SNH–SNH, and other strategies will be discussed. Intramolecular SNH reactions will also be considered as effective synthetic tools to obtain condensed heterocyclic systems.

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22

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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23

ZHANALIYEVA, R. N., B. B. TORSYKBAYEVA, M. O. ALTYNBEKOVA, B. S. IMANGALIYEVA, and A. Zh NAZAROVA. "SYNTHESIS OF 2- (2I – ACYLOXY-ETHOXY) ETHYL CHLORIDE AND THEIR INTERACTION WITH AMIDES AND ALKALI METAL RHODANIDES." Periódico Tchê Química 16, no. 32 (2019): 996–1009. http://dx.doi.org/10.52571/ptq.v16.n32.2019.1013_periodico32_pgs_996_1009.pdf.

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This work is aimed at studying the reaction of nucleophilic substitution of the chlorine atom in 2-(2'-acyloxy-ethoxy) ethylchlorides with amines and a rhodanide ion and developing methods of synthesizing a 2-(2'-acyloxy-ethoxy) ethylchlorides, rhodanides, and their derivatives previously unknown in specialized literature. In the chlorohydrin molecule of diethylene glycol, there are two reaction centers that allow carrying out nucleophilic substitution reactions, as well as reactions that promote them with electrophilic reagents. The authors carried out several experiments for acylating diethy

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24

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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25

Baum, James Clayton, Jimat Bolhassan, Richard Francis Langler, Paul Joseph Pujol, and Raj Kumar Raheja. "Sulfonyl esters. 2. CS cleavage in some substitution reactions of nitrobenzenesulfonates." Canadian Journal of Chemistry 68, no. 8 (1990): 1450–55. http://dx.doi.org/10.1139/v90-222.

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An attempt to explore aromatic sulfonate esters as agents for the condensation of alcohols with mercaptans revealed an unusual process for sulfonate esters: CS bond rupture. Two mechanistic possibilities for CS bond rupture are explored: (i) radical anion intermediacy via single electron transfer and (ii) nucleophilic aromatic substitution. Both experiments and molecular orbital computations are presented to support the conclusion that nucleophilic aromatic substitutions are occurring. Keywords: sulfonyl esters, nitrobenzenesulfonates, CS bond rupture.

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26

Shen, Shusu. "Nucleophilic Substitution Reactions at Vinylic Carbons." Chinese Journal of Organic Chemistry 34, no. 12 (2014): 2448. http://dx.doi.org/10.6023/cjoc201406046.

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27

Rossi, Roberto A., Adriana B. Pierini, and Alicia B. Peñéñory. "Nucleophilic Substitution Reactions by Electron Transfer." Chemical Reviews 103, no. 1 (2003): 71–168. http://dx.doi.org/10.1021/cr960134o.

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28

Yew, Kyoung Han, Han Joong Koh, Hai Whang Lee, and Ikchoon Lee. "Nucleophilic substitution reactions of phenyl chloroformates." Journal of the Chemical Society, Perkin Transactions 2, no. 12 (1995): 2263. http://dx.doi.org/10.1039/p29950002263.

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29

Lennon, Patrick J., David P. Mack, and Quentin E. Thompson. "Nucleophilic catalysis of organosilicon substitution reactions." Organometallics 8, no. 4 (1989): 1121–22. http://dx.doi.org/10.1021/om00106a043.

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30

McGeary, Ross P., Sara Rasoul Amini, Vincent W. S. Tang, and Istvan Toth. "Nucleophilic Substitution Reactions of Pyranose Polytosylates." Journal of Organic Chemistry 69, no. 8 (2004): 2727–30. http://dx.doi.org/10.1021/jo035779k.

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31

Tatke, D. R., and S. Seshadrif. "Nucleophilic substitution reactions of azabenzanthrone derivatives." Dyes and Pigments 7, no. 2 (1986): 153–58. http://dx.doi.org/10.1016/0143-7208(86)85005-7.

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32

Moiseev, I. K., E. I. Bagrii, Yu N. Klimochkin, T. N. Dolgopolova, M. N. Zemtsova, and P. L. Trakhtenberg. "Adamantanol nitrates in nucleophilic substitution reactions." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 34, no. 9 (1985): 1983–85. http://dx.doi.org/10.1007/bf00953951.

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33

Okhlobystina, Aleksandra V., Andrey O. Okhlobystin, Nadezhda T. Berberova, and Daria A. Burmistrova. "HYDROGEN SULFIDE IN NUCLEOPHILIC SUBSTITUTION REACTIONS OF HYDROXY GROUPS IN AROMATIC ALCOHOLS." IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENIY KHIMIYA KHIMICHESKAYA TEKHNOLOGIYA 61, no. 9-10 (2018): 36–41. http://dx.doi.org/10.6060/ivkkt.20186109-10.5716.

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Most methods of obtaining aromatic thiols are based on nucleophilic substitution reactions at halogen derivatives of aromatic hydrocarbons when used as nucleophilic reagents sodium thiolate, thiourea or potassium xanthate at high temperatures, pressure and in the presence of catalysts. The direct reaction of nucleophilic substitution of OH-groups in the phenols, pyrocatechol and benzyl alcohol to the HS-group in conditions of one-electron reducrion of hydrogen sulfide in acetonitrile and pyridinium ionic liquid was investigated for the first time. The proposed reactions proceed at room tempera

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34

Mclure, FI, RK Norris, and K. Wilson. "Nucleophilic Substitution Reactions of Thienyl Neopentyl Substrates." Australian Journal of Chemistry 40, no. 1 (1987): 49. http://dx.doi.org/10.1071/ch9870049.

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The reaction of the chlorides (4)-(6), which are both neopentylic and thenylic , were studied. The chloride (4), unlike its analogue (13) in the benzene series, undergoes ready solvolysis with alcohols to give the corresponding ethers, e.g. (7)-(9). The chlorides (5) and (6) react more slowly than (4) but undergo methanolysis to give the methyl ethers (11) and (12) respectively. In the dipolar aprotic solvents, dimethyl sulfoxide and dimethylformamide, the reactions of the chlorides (4), (5) and (6) with the thiolate salt (16) appear to proceed by an SN1-like, an SN(AEAE) and an SRNl process r

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35

Sheyi, Rotimi, Anamika Sharma, Ayman El-Faham, Beatriz G. de la Torre, and Fernando Albericio. "Phenol as a Modulator in the Chemical Reactivity of 2,4,6-Trichloro-1,3,5-triazine: Rules of the Game II." Australian Journal of Chemistry 73, no. 4 (2020): 352. http://dx.doi.org/10.1071/ch19524.

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2,4,6-Trichloro-1,3,5-triazine (TCT) is a privileged core that has the capacity to undergo sequential nucleophilic substitution reactions. Three nucleophiles, namely phenol, thiol and amine, were studied and the preferential order of incorporation on TCT was found to be first phenol, second thiol and third amine. The introduction of phenol was achieved at −20°C. The incorporation of this nucleophile in TCT helped to replace the third ‘Cl’ at 35°C, which is compatible with a biological context. The atomic charges on ‘Cl’ calculated by theoretical approaches were consistent with the experimental

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36

Wang, Jianghong, Ashot Kh Khanamiryan, and Clifford C. Leznoff. "Multisubstituted phthalonitriles for phthalocyanine synthesis." Journal of Porphyrins and Phthalocyanines 08, no. 11 (2004): 1293–99. http://dx.doi.org/10.1142/s1088424604000660.

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3,4,5,6-tetrafluorophthalonitrile and 3,4,5,6-tetrachlorophthalonitrile were used as substrates with various phenoxides to prepare 3,4,6-trihalo-5-p-substitutedphenoxyphthalonitriles, containing four substituents other than hydrogen, by nucleophilic aromatic substitution reactions. Subsequent reactions with unsymmetrical catechols gave tetrasubstitutedphthalonitriles, having four different substituents. In one instance, attempts to displace the last remaining fluoro group by an octanoxide nucleophile led to substitution of a p-methylphenoxy group, showing that phenoxy substituents are also lab

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37

Abd-El-Aziz, Alaa S., Christine R. de Denus, and Harold M. Hutton. "Ironcyclopentadienyl mediated 2-alkyl-2-arylphenylsulphonylacetonitrile synthesis." Canadian Journal of Chemistry 73, no. 2 (1995): 289–95. http://dx.doi.org/10.1139/v95-039.

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A unique route to the synthesis of 2-alkyl-2-arylphenylsulphonylacetonitriles via the nucleophilic aromatic substitution (SNAr) of chloroarene cyclopentadienyliron complexes with 2-alkyl phenylsulphonylacetonitriles has been investigated. Reactions of chloroarene complexes (1a–d) with 2-alkyl phenylsulphonylacetonitrile (2a,b) in the presence of K2CO3 in DMF at room temperature led to the formation of complexes 3a–d and 4a,c,d in good yields. The use of alkylated phenylsulphonylacetonitriles as nucleophiles in the reactions with the p-dichlorobenzene complex (1e) allowed the formation of the d

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38

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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39

Feng, Shouai, Yixin Li, Hong Liu, et al. "Mesoporous Silica for Triphase Nucleophilic Substitution Reactions." CHIMIA International Journal for Chemistry 72, no. 7 (2018): 514–17. http://dx.doi.org/10.2533/chimia.2018.514.

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40

Rossi, Roberto, and Al Postigo. "Recent Advances on Radical Nucleophilic Substitution Reactions." Current Organic Chemistry 7, no. 8 (2003): 747–69. http://dx.doi.org/10.2174/1385272033486729.

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41

Barrett, Anthony G. M., D. Christopher Braddock, Rachel A. James, Nobuyuki Koike, and Panayiotis A. Procopiou. "Nucleophilic Substitution Reactions of (Alkoxymethylene)dimethylammonium Chloride." Journal of Organic Chemistry 63, no. 18 (1998): 6273–80. http://dx.doi.org/10.1021/jo980583j.

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42

Matveeva, E. D., T. A. Podrugina, Yu K. Grishin, A. S. Pavlova, and N. S. Zefirov. "Phosphonium-iodonim ylides in nucleophilic substitution reactions." Russian Journal of Organic Chemistry 43, no. 2 (2007): 201–6. http://dx.doi.org/10.1134/s107042800702008x.

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43

GUO, C. Y., R. L. KIRCHMEIER, and J. M. SHREEVE. "ChemInform Abstract: Nucleophilic Substitution Reactions of Polyfluoroalkylsulfonamides." ChemInform 23, no. 3 (2010): no. http://dx.doi.org/10.1002/chin.199203088.

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Żwawiak, Justyna, and Lucjusz Zaprutko. "Reactions of Nucleophilic Substitution in Bicyclic Nitroimidazodihydrooxazoles." Journal of Heterocyclic Chemistry 51, no. 5 (2014): 1463–67. http://dx.doi.org/10.1002/jhet.1907.

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Narasaka, Koichi, Shunsuke Chiba, and Kaori Ando. "Concerted Nucleophilic Substitution Reactions at Vinylic Carbons." Synlett 2009, no. 16 (2009): 2549–64. http://dx.doi.org/10.1055/s-0029-1217752.

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46

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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Kutschy, Peter, Pavol Kristian, Milan Dzurilla, Dušan Koščík, and Róbert Nádaskay. "Selectivity of nucleophilic addition to and substitution at isothiocyanatocarbonyl group. Reactions of 4-pentinoyl- and 2-(2-propinyl)-4-pentinoyl isothiocyanate with amines and methanol." Collection of Czechoslovak Chemical Communications 52, no. 4 (1987): 995–1005. http://dx.doi.org/10.1135/cccc19870995.

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Abstract:

4-Pentinoyl isothiocyanate reacts with primary and secondary amines by either nucleophilic addition to N=C=S group to yield the corresponding thioureas, or a nucleophilic substitution at the carbonyl group to give 4-pentinoic acid amides. The less nucleophilic diphenylamine reacts selectively to afford the product of nucleophilic addition only. 2-(2-Propinyl)-4-pentinoyl isothiocyanate, having a sterically hindered carbonyl group, furnished with primary amines a mixture of amides and thioureas, whereas the bulkier secondary amines react selectively to form thioureas only. Both isothiocyanates

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48

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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Aurell, María J., Miguel A. González-Cardenete, and Ramón J. Zaragozá. "A new mechanism for internal nucleophilic substitution reactions." Organic & Biomolecular Chemistry 16, no. 7 (2018): 1101–12. http://dx.doi.org/10.1039/c7ob02994b.

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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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