Gutmann's Donor Numbers Correctly Assess the Effect of the Solvent on the Kinetics of SN Ar Reactions in Ionic Liquids

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dc.contributor.authorAlarcón-Espósito, Jazmín
dc.contributor.authorContreras, Renato
dc.contributor.authorTapia, Ricardo A
dc.contributor.authorCampodónico, Paola
dc.date.accessioned2021-12-23T21:28:18Z
dc.date.available2021-12-23T21:28:18Z
dc.date.issued2016
dc.description.abstractWe report an experimental study on the effect of solvents on the model SN Ar reaction between 1-chloro-2,4-dinitrobenzene and morpholine in a series of pure ionic liquids (IL). A significant catalytic effect is observed with reference to the same reaction run in water, acetonitrile, and other conventional solvents. The series of IL considered include the anions, NTf2 (-) , DCN(-) , SCN(-) , CF3 SO3 (-) , PF6 (-) , and FAP(-) with the series of cations 1-butyl-3-methyl-imidazolium ([BMIM](+) ), 1-ethyl-3-methyl-imidazolium ([EMIM](+) ), 1-butyl-2,3-dimethyl-imidazolium ([BM2 IM](+) ), and 1-butyl-1-methyl-pyrrolidinium ([BMPyr](+) ). The observed solvent effects can be attributed to an "anion effect". The anion effect appears related to the anion size (polarizability) and their hydrogen-bonding (HB) abilities to the substrate. These results have been confirmed by performing a comparison of the rate constants with Gutmann's donicity numbers (DNs). The good correlation between rate constants and DN emphasizes the major role of charge transfer from the anion to the substrate.es
dc.identifier.citationAlarcón-Espósito J, Contreras R, Tapia RA, Campodónico PR. Gutmann's Donor Numbers Correctly Assess the Effect of the Solvent on the Kinetics of SN Ar Reactions in Ionic Liquids. Chemistry. 2016 Sep 5;22(37):13347-51.es
dc.identifier.urihttp://dx.doi.org/10.1002/chem.201602237es
dc.identifier.urihttp://hdl.handle.net/11447/5282
dc.language.isoen_USes
dc.subjectGutmann's donicity numberses
dc.subjectLewis acidity/basicityes
dc.subjectAnion (solvent) effectses
dc.subjectIonic liquidses
dc.titleGutmann's Donor Numbers Correctly Assess the Effect of the Solvent on the Kinetics of SN Ar Reactions in Ionic Liquidses
dc.typeArticlees

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