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Reactivity indices profile: a companion tool of the potential energy surface for the analysis of reaction mechanisms. Nucleophilic aromatic substitution reactions as test case

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dc.contributor.author Ormazábal-Toledo, Rodrigo
dc.contributor.author Contreras, Renato
dc.contributor.author Campodonico, Paola
dc.date.accessioned 2017-04-10T13:03:44Z
dc.date.available 2017-04-10T13:03:44Z
dc.date.issued 2013
dc.identifier.citation J. Org. Chem., 2013, 78 (3), pp 1091–1097 es_CL
dc.identifier.uri http://dx.doi.org/10.1021/jo3025048 es_CL
dc.identifier.uri http://hdl.handle.net/11447/1119
dc.description Centro de Química Médica es_CL
dc.description.abstract We herein report on the usefulness of the reactivity indices profiles along a reaction coordinate. The model is tested to fully describe the reaction mechanism of the title reactions. Group nucleophilicity and electrophilicity profiles help describe the bond-breaking/bond-formation processes and the intramolecular electron density reorganization. The reactivity indices’ profile analysis is consistently complemented with hydrogen bonding (HB) effects along the reaction coordinate: the final outcome of the reaction is determined by the stage at which the HB complex can be formed. Transition-state structures located for six reactions studied, including the charged nucleophile thiocyanate, show that the main stabilizing interaction is that formed between the hydrogen atom of the nucleophile and the o-NO2 group. This result discards the role of HB interaction between the nucleophile and the leaving group previously proposed in the literature. es_CL
dc.format.extent 7 es_CL
dc.language.iso en_US es_CL
dc.publisher American Chemical Society es_CL
dc.subject Reactivity Indices es_CL
dc.subject hydrogen bonding es_CL
dc.subject reaction coordinate es_CL
dc.title Reactivity indices profile: a companion tool of the potential energy surface for the analysis of reaction mechanisms. Nucleophilic aromatic substitution reactions as test case es_CL
dc.type Artículo es_CL


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