with regards to nucleophilic substitution reactions, electron-rich species are relatively strong nucleophiles, as judged by rates of attack by electrophiles. For example, compared to benzene, pyrrole is more rapidly attacked by electrophiles. Pyrrole is therefore considered to be an electron-rich aromatic ring.[5] Similarly, benzene derivatives with electron-donating groups (EDGs) are attacked by electrophiles faster than in benzene.[6] The electron-donating vs electron-withdrawing influence of various functional groups have been extensively parameterized in linear free energy relationships.
^Rosokha, Sergiy V.; Kochi, Jay K. (2008). "Fresh Look at Electron-Transfer Mechanisms via the Donor/Acceptor Bindings in the Critical Encounter Complex". Accounts of Chemical Research. 41 (5): 641–653. doi:10.1021/ar700256a. PMID 18380446.
^Lappert, Michael F. (1988). "The Coordination Chemistry of Electron-Rich Alkenes (Enetetramines)". Journal of Organometallic Chemistry. 358 (1–3): 185–213. doi:10.1016/0022-328X(88)87079-7.
^Stalder, Romain; Mei, Jianguo; Graham, Kenneth R.; Estrada, Leandro A.; Reynolds, John R. (2014). "Isoindigo, a Versatile Electron-Deficient Unit for High-Performance Organic Electronics". Chemistry of Materials. 26: 664–678. doi:10.1021/cm402219v.
^Buß, Florenz; Mehlmann, Paul; Mück-Lichtenfeld, Christian; Bergander, Klaus; Dielmann, Fabian (2016). "Reversible Carbon Dioxide Binding by Simple Lewis Base Adducts with Electron-Rich Phosphines". Journal of the American Chemical Society. 138 (6): 1840–1843. doi:10.1021/jacs.5b13116. PMID 26824487.
^Davies, Huw M. L.; Hedley, Simon J. (2007). "Intermolecular Reactions of Electron-Rich heterocycles with Copper and Rhodium Carbenoids". Chemical Society Reviews. 36 (7): 1109–1119. doi:10.1039/b607983k. PMID 17576478.
^Lindsay Smith, J. R.; McKeer, L. C.; Taylor, J. M. "4-Chlorination of Electron-Rich Benzenoid Compounds: 2,4-Dichloromethoxybenzene". Organic Syntheses. 67: 222. doi:10.15227/orgsyn.067.0222; Collected Volumes, vol. 8, p. 167.
^Hawthorne, M. Frederick; Zheng, Zhiping (1997). "Recognition of Electron-Donating Guests by Carborane-Supported Multidentate Macrocyclic Lewis Acid Hosts: Mercuracarborand Chemistry". Accounts of Chemical Research. 30 (7): 267–276. doi:10.1021/ar9501479.
January 01, 1970
electron, rich, jargon, that, used, multiple, related, meanings, with, either, both, kinetic, thermodynamic, implications, with, regards, electron, transfer, electron, rich, species, have, ionization, energy, reducing, agents, tetrakis, dimethylamino, ethylene. Electron rich is jargon that is used in multiple related meanings with either or both kinetic and thermodynamic implications with regards to electron transfer electron rich species have low ionization energy and or are reducing agents 1 Tetrakis dimethylamino ethylene is an electron rich alkene because unlike ethylene it forms isolable radical cation 2 In contrast electron poor alkene tetracyanoethylene is an electron acceptor forming isolable anions 3 with regards to acid base reactions electron rich species have high pKa s and react with weak Lewis acids 4 with regards to nucleophilic substitution reactions electron rich species are relatively strong nucleophiles as judged by rates of attack by electrophiles For example compared to benzene pyrrole is more rapidly attacked by electrophiles Pyrrole is therefore considered to be an electron rich aromatic ring 5 Similarly benzene derivatives with electron donating groups EDGs are attacked by electrophiles faster than in benzene 6 The electron donating vs electron withdrawing influence of various functional groups have been extensively parameterized in linear free energy relationships with regards to Lewis acidity electron rich species are strong Lewis bases 7 See also editElectron withdrawing groupReferences edit Rosokha Sergiy V Kochi Jay K 2008 Fresh Look at Electron Transfer Mechanisms via the Donor Acceptor Bindings in the Critical Encounter Complex Accounts of Chemical Research 41 5 641 653 doi 10 1021 ar700256a PMID 18380446 Lappert Michael F 1988 The Coordination Chemistry of Electron Rich Alkenes Enetetramines Journal of Organometallic Chemistry 358 1 3 185 213 doi 10 1016 0022 328X 88 87079 7 Stalder Romain Mei Jianguo Graham Kenneth R Estrada Leandro A Reynolds John R 2014 Isoindigo a Versatile Electron Deficient Unit for High Performance Organic Electronics Chemistry of Materials 26 664 678 doi 10 1021 cm402219v Buss Florenz Mehlmann Paul Muck Lichtenfeld Christian Bergander Klaus Dielmann Fabian 2016 Reversible Carbon Dioxide Binding by Simple Lewis Base Adducts with Electron Rich Phosphines Journal of the American Chemical Society 138 6 1840 1843 doi 10 1021 jacs 5b13116 PMID 26824487 Davies Huw M L Hedley Simon J 2007 Intermolecular Reactions of Electron Rich heterocycles with Copper and Rhodium Carbenoids Chemical Society Reviews 36 7 1109 1119 doi 10 1039 b607983k PMID 17576478 Lindsay Smith J R McKeer L C Taylor J M 4 Chlorination of Electron Rich Benzenoid Compounds 2 4 Dichloromethoxybenzene Organic Syntheses 67 222 doi 10 15227 orgsyn 067 0222 Collected Volumes vol 8 p 167 Hawthorne M Frederick Zheng Zhiping 1997 Recognition of Electron Donating Guests by Carborane Supported Multidentate Macrocyclic Lewis Acid Hosts Mercuracarborand Chemistry Accounts of Chemical Research 30 7 267 276 doi 10 1021 ar9501479 Retrieved from https en wikipedia org w index php title Electron rich amp oldid 1216192551, wikipedia, wiki, book, books, library,
