Research Output

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Mechanistic pathways of aromatic nucleophilic substitution in conventional solvents and ionic liquids

2014 , Marcela Gazitúa , Ricardo A. Tapia , Renato Contreras , CAMPODONICO GALDAMES, PAOLA ROSSANA

Solvation effects on the reaction mechanism for nucleophilic substitution reactions have been kinetically evaluated in conventional solvents and ionic liquids.

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Changes in the SNAr reaction mechanism brought about by preferential solvation

2015 , Jazmín Alarcón-Espósito , Ricardo A. Tapia , Renato Contreras , CAMPODONICO GALDAMES, PAOLA ROSSANA

For model SNAr reactions in mixtures of acetonitrile and water, we found preferential solvation in favor of the aqueous phase.

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Experimental Analyses Emphasize the Stability of the Meisenheimer Complex in a SNAr Reaction Toward Trends in Reaction Pathways

2020 , CAMPODONICO GALDAMES, PAOLA ROSSANA , OLIVARES, MARIA BELEN , Ricardo A. Tapia

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Effect of the nature of the nucleophile and solvent on an SNAr reaction

2018 , Marcela Gazitúa , Ricardo A. Tapia , Renato Contreras , CAMPODONICO GALDAMES, PAOLA ROSSANA

The reaction of 2,4-dinitrobenzenesulfonyl chloride toward propylamine was kinetically evaluated in 19 organic solvents and 10 ionic liquids as reaction media.

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How the Nature of an Alpha-Nucleophile Determines a Brønsted Type-Plot and Its Reaction Pathways. An Experimental Study

2022 , CAMPODONICO GALDAMES, PAOLA ROSSANA , Ricardo A. Tapia , Cristian Suárez-Rozas

The reactions between 2-chloro-5-nitro pyrimidine with a serie of α-nucleophile derivatives were kinetically evaluated. The kinetic study was carried out in aqueous media and the data shown an unusual split on the Brønsted type-plot, opening a controversial discussion based on reactivities and possible reaction pathways. These split Brønsted type-plots are discussed over the hypothetical transition state (TS) structures associated to concerted or stepwise mechanisms with emphasis on hydrogen bond interactions between electrophile/nucleophile pair able to determine the reactivities and the plausible reaction routes.

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Specific nucleophile–electrophile interactions in nucleophilic aromatic substitutions

2013 , Rodrigo Ormazábal-Toledo , Renato Contreras , Ricardo A. Tapia , CAMPODONICO GALDAMES, PAOLA ROSSANA

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

2016 , Jazmín Alarcón-Espósito , Renato Contreras , Ricardo A. Tapia , CAMPODONICO GALDAMES, PAOLA ROSSANA

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Activation of Electrophile/Nucleophile Pair by a Nucleophilic and Electrophilic Solvation in a SNAr Reaction

2018 , Bruno Sánchez , Cristian Calderón , Ricardo A. Tapia , Renato Contreras , CAMPODONICO GALDAMES, PAOLA ROSSANA

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Synthesis and characterization of poly (ionic liquid) derivatives of N -alkyl quaternized poly(4-vinylpyridine)

2018 , XIMENA GABRIELA BRIONES OLARAN , Ricardo A. Tapia , CAMPODONICO GALDAMES, PAOLA ROSSANA , Marcela Urzúa , Ángel Leiva , Renato Contreras , Javier González-Navarrete

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Site activation effects promoted by intramolecular hydrogen bond interactions in SNAr reactions

2014 , Sebastián Gallardo-Fuentes , Ricardo A. Tapia , Renato Contreras , CAMPODONICO GALDAMES, PAOLA ROSSANA

The nucleophilic aromatic substitution reaction of benzohydrazide derivatives towards 2-chloro-5-nitropyrimidine is used as model system to experimentally and theoretically show that intramolecular hydrogen-bond formation operates as a perturbation that elicits a dual response at the reaction center of the transition state (TS) structure.