2018 |
Gazitua, M; Tapia, R A; Contreras, R; Campodonico, P R Effect of the Nature of the Nucleophile and Solvent on an Snar Reaction Artículo de revista New Journal of Chemistry, 42 (1), pp. 260-264, 2018, ISSN: 1144-0546. Resumen | Enlaces | BibTeX | Etiquetas: amines, aromatic aryl azides, conventional ionic kinetics, liquids, preferential reaction-mechanism, regioselectivity solvation, solvents, substitutions, temperature @article{RN422, title = {Effect of the Nature of the Nucleophile and Solvent on an Snar Reaction}, author = { M. Gazitua and R.A. Tapia and R. Contreras and P.R. Campodonico}, url = {/brokenurl#<Go to ISI>://WOS:000418369000027}, doi = {10.1039/c7nj03212a}, issn = {1144-0546}, year = {2018}, date = {2018-01-01}, journal = {New Journal of Chemistry}, volume = {42}, number = {1}, pages = {260-264}, abstract = {The reaction of 2,4-dinitrobenzenesulfonyl chloride toward propylamine was kinetically evaluated in 19 organic solvents and 10 ionic liquids as reaction media. This study was compared with a previous study to experimentally show that solvent effects and the nature of the reacting pair drastically affect the reaction rate and the reaction mechanism. While the reaction of the reference electrophile 2,4-dinitrobenzenesulfonyl chloride with piperidine is favored in polar solvents with the ability to donate or accept hydrogen bonds, the reaction with propylamine is favored in solvents with the ability to accept hydrogen bonds.}, keywords = {amines, aromatic aryl azides, conventional ionic kinetics, liquids, preferential reaction-mechanism, regioselectivity solvation, solvents, substitutions, temperature}, pubstate = {published}, tppubtype = {article} } The reaction of 2,4-dinitrobenzenesulfonyl chloride toward propylamine was kinetically evaluated in 19 organic solvents and 10 ionic liquids as reaction media. This study was compared with a previous study to experimentally show that solvent effects and the nature of the reacting pair drastically affect the reaction rate and the reaction mechanism. While the reaction of the reference electrophile 2,4-dinitrobenzenesulfonyl chloride with piperidine is favored in polar solvents with the ability to donate or accept hydrogen bonds, the reaction with propylamine is favored in solvents with the ability to accept hydrogen bonds. |
2015 |
Perez-Mendez, C; Contreras, R Quantitative Characterization of the Global Philicity Patterns of Common Diene/Dienophile Pairs in Cycloaddition Reactions Ii: The Interacting Pair Model Artículo de revista Tetrahedron Letters, 56 (14), pp. 1767-1770, 2015, ISSN: 0040-4039. Resumen | Enlaces | BibTeX | Etiquetas: amines, charge cycloaddition, diels-alder electronegativity, electrophilicity, hardness, mechanism, michael nucleophilicity, reactions, reactivity @article{RN272, title = {Quantitative Characterization of the Global Philicity Patterns of Common Diene/Dienophile Pairs in Cycloaddition Reactions Ii: The Interacting Pair Model}, author = { C. Perez-Mendez and R. Contreras}, url = {/brokenurl#<Go to ISI>://WOS:000351790700004}, doi = {10.1016/j.tetlet.2015.01.199}, issn = {0040-4039}, year = {2015}, date = {2015-01-01}, journal = {Tetrahedron Letters}, volume = {56}, number = {14}, pages = {1767-1770}, publisher = {2015 Elsevier Ltd.}, abstract = {We present a unified model of electrophilicity and nucleophilicity that considers the electrophile/nucleophile pair in an interacting regime, thereby avoiding the arbitrariness of defining them as the opposite ends of a unique reactivity scale. The model is validated against rate coefficients for the cycloaddition of azomethine ylides towards substituted acetylenes and Michael addition of a series of 1-(X-substituted pheny1)-2-propyn-1-ones towards hydrazine.}, keywords = {amines, charge cycloaddition, diels-alder electronegativity, electrophilicity, hardness, mechanism, michael nucleophilicity, reactions, reactivity}, pubstate = {published}, tppubtype = {article} } We present a unified model of electrophilicity and nucleophilicity that considers the electrophile/nucleophile pair in an interacting regime, thereby avoiding the arbitrariness of defining them as the opposite ends of a unique reactivity scale. The model is validated against rate coefficients for the cycloaddition of azomethine ylides towards substituted acetylenes and Michael addition of a series of 1-(X-substituted pheny1)-2-propyn-1-ones towards hydrazine. |
2018 |
Effect of the Nature of the Nucleophile and Solvent on an Snar Reaction Artículo de revista New Journal of Chemistry, 42 (1), pp. 260-264, 2018, ISSN: 1144-0546. |
2015 |
Quantitative Characterization of the Global Philicity Patterns of Common Diene/Dienophile Pairs in Cycloaddition Reactions Ii: The Interacting Pair Model Artículo de revista Tetrahedron Letters, 56 (14), pp. 1767-1770, 2015, ISSN: 0040-4039. |