Reactions of Aryl Acetates with Secondary Alicyclic Amines in Ethanol/Water Mixtures: Effect of the Solvent Composition on the Kinetics and Mechanism

dc.contributor.authorCastro, Enrique A.
dc.contributor.authorMillan, Daniela
dc.contributor.authorAguayo, Raúl
dc.contributor.authorCampodónico, Paola
dc.contributor.authorSantos, José G.
dc.date.accessioned2016-12-12T21:08:22Z
dc.date.available2016-12-12T21:08:22Z
dc.date.issued2011
dc.description.abstractWe report a kinetic study on the reactions of secondary alicyclic amines toward 4-nitrophenyl, 2,4-dinitrophenyl, and 2,4,6-trinitrophenyl acetates (1, 2, and 3) in ethanol/water mixtures of different compositions. It is found that (i) the intermediate in the reaction of 1 is stabilized in a mixture of 90 vol% ethanol; (ii) for the reaction of 2, the mechanism is stepwise in water but concerted in the mixtures; (iii) For the reaction of 3, the mechanism is concerted along the whole range of composition; (iv) the effect of -NO(2) outweighs the solvent effect; (v) preferential solvation in the core of reaction can be ruled out. (C) 2011 Wiley Periodicals, Inc. Int J Chem Kinet 43: 687-693, 2011
dc.identifier.citationInternational Journal of Chemical Kinetics, 2011, vol. 43, n° 12, p. 687-693
dc.identifier.urihttp://hdl.handle.net/11447/882
dc.identifier.urihttp://dx.doi.org/10.1002/kin.20598
dc.language.isoen_US
dc.subjectStructure-reactivity correlations
dc.subjectX-Substituted benzoates
dc.subject2,4,6-Trinitrophenyl methyl carbonate
dc.subjectRate-determining step
dc.subjectAqueous-ethanol
dc.subject2,4-Dinitrophenyl acetate
dc.subjectEster aminolysis
dc.subjectPhenyl carbonate
dc.subjectNonleaving group
dc.subjectPyridinolysis
dc.titleReactions of Aryl Acetates with Secondary Alicyclic Amines in Ethanol/Water Mixtures: Effect of the Solvent Composition on the Kinetics and Mechanism
dc.typeArtículo

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